I like trannys. I love the taboo of lifting up a skirt, seeing a dick and the sucking it.

Saturday night, being alone, horny and bored I surfed the casual encounters section of Craigslist under T4M. Found a tranny in my area who was looking for a no strings attached hook up. This one was also a VERS (top and bottom) and that was something I had been wanting to experience. Wasn't sure if I was ready to get pounded, but I at least wanted the option.

I got there, was invited in and as we talked, tranny told me that there was a spouse. I was nervous at this point and that said spouse was home. I was nervous. No advanced warning, I wasn't exactly quiet. The marriage is open and the spouse was told that I was coming over and why. So I was a bit calmer. Then I was asked "Do you want to meet my wife?" I wasn't expecting that question, but I agreed because I know some people in an open marriage want their spouse to meet their fling as a sign of honesty or something.

She entered the room and come to find out, the spouse was another male to female tranny. That was also unexpected, but what ever. So the three of us talked, then the spouse asked "Aren't you here to fuck my wife?"

I answered "Yes, I just was waiting for you to leave."

"You think you two are going to have sex and I get nothing?"

By this point my dick was about to tear through my pants. I thought she was still screwing with me, but part of me knew she was serious. I was about to ask another question when she said "Either get on with it or leave."

That's when I felt a pair of lips on my mouth. The tranny I met on line and I started kissing and undressing each other while the spouse watched. I have been watched before, but those were times when I was having sex with a woman. Here someone was watching me, and stroking themself while I sucked a dick.

This was suck a turn on that I came while I was on my knees. I was rubbing myself while sucking and getting dick slapped. I wasn't ready to be done just yet, and neither were they. I stood up and was ordered to bend over the arm of the couch. I watched as the tranny picked up the bottle of astroglide. Her spouse was now in just a bra. Her nightie was removed sometime before and her dick was in her hand. She was passable transvestite, no hormones, perfectly working dick.

I felt the dick head against my asshole and slowly my asshole opening up to accept it. I was getting it, my first time, bareback. My dick was hardening again.

I felt the dick slide out of me and felt the cum on my back. I then looked up to see the spouse come towards me, stroking her dick. I watched as she came over my face.

I laid on the couch, stroking myself as they watched. I asked them to call me a "cum covered faggot", and as they did I came on their floor.

I drove home in a bit of shame...and still get hard thinking about it.

With the house all to myself from Thursday through Sunday night, I suggested to Robby (our gang bang guru) that it would be great for him to arrange a fuck session where we could take advantage of an empty house for a change, rather than renting a hotel room for our activities. He came through within the first couple of hours, which just shows what an amazing track record he has of snagging seriously fuckable women.

He'd connected with Jamie via a Craigslist ad. She's 30, 5-5 120, with blonde-highlighted light brown hair and 32B tits. The photo posted here is the one she sent along with her request to meet. Because it was midday Thursday, Robby was only able to arrange a threesome, since the rest of the guys in our over-50 GB group couldn't make it on such short notice. Jamie was apparently OK with that, though, since this was to be her first multi-guy sex encounter and she wasn't too sure how overwhelmed she might be with more participants. And if her claims could be believed, it would prove the first time in more than a month that she'd had any kind of sex at all.

While waiting for them to show up, I gave Robby some shit via text because, after picking Jamie up from her place in North Denver, he had trouble finding my house on the southeast side. He claimed his GPS was all fucked up, but I was more certain it was operator error. Also on the way over, he "warned" me that Jamie was a bit on the skanky side, but I replied that, given our plans for the afternoon, that was a benefit rather than a flaw.

They showed up at my place just before 1:00 p.m., around 20 minutes late. I'd prepared our guest room in advance by stripping the queen-size bed and putting on a new bottom sheet plus clean pillow cases, setting out a brand-new tube of lube, and adjusting the shades so the room wouldn't be quite so bright. Meeting them at the front door, I saw that Jamie was dressed in a pleasantly slutty outfit: Short green cloth jacket over a black lace sleeveless top with a purple bra showing underneath, a denim micro-mini skirt that barely covered her ass, and over-the-knee high-heeled leather boots. She had her hair tied back in a ponytail and spun around after coming through the door so I could apply the green silk scarf I was using as a blindfold. She'd asked for this as one of the conditions of the afternoon's activities, and I was happy to oblige.

Given the lateness of their arrival and the fact Robby had to leave in an hour to pick up his kids from school, we immediately headed upstairs and got down to business. I helped Jamie off with her jacket and unzipped her skirt so she could slip it off. She quickly removed her lacy top and I unhooked her bra. We all agreed she could leave her boots on for the duration. Meanwhile, Robby was stripping down to bare skin, tossing his clothes haphazardly onto the floor in his haste to start in on Jamie. She asked us to leave her undershorts on -- they were leopard-print boy-shorts -- which was fine because they'd been altered by having two carefully placed holes cut out of the crotch. One showed off her smoothly shaved pussy while the other exposed her tight little asshole. I ran my hand down over her buttocks and slipped my middle finger into her tight, wet pussy while removing my clothes at a pace considerably slower than Robby had achieved. He put his hands on her small, firm tits and began to suck on her nipples, which stood up nicely to the attention. She used one of her hands to tug on his fully erect cock - it was hard even before he took off his trousers -- and meanwhile I disengaged so I could remove the rest of my clothes as well.

Robby suggested she lie on her back, which she did, and he stuck his face in between her thighs to taste some of that sweet, sweet pussy. I thought he might be down there a while, but after only about a minute of some serious licking he stood up, pulled her hips closer to the edge of the mattress, and jammed his seven-inch dick into her wet slit. She had her legs up in the air with Robby pressing his hands against the backs of her thighs to keep them there as he pounded her hard. I'd stroked myself from a semi-hard to a fully erect state and climbed onto the bed so she could take my dick in her mouth. By changing my angle of approach, I was able to slide my entire member into her mouth. Of course I'm less than six inches, so it's not a huge challenge, but I could still sense the tip of my cock hit the back of her throat with every downward thrust, which was a great feeling.

After a few minutes of fucking her while standing alongside the bed, Robby suggested it was my turn to squeeze my dick into that pussy. We helped flip her over -- her equilibrium was compromised somewhat by the blindfold -- and I entered her from behind, doggie-style. It had been a couple of months since I'd had sex, so this was a welcome opportunity and I made the most of it, thrusting enthusiastically as Jamie reached down with her right hand and rubbed it briskly across her clit. Meanwhile, Robby had opened up the small bottle of Astroglide he'd brought with him and suggested we DP the girl. She was definitely on board with that idea, so we maneuvered ourselves into position with me on my back and her on top, facing me. She reached down and re-inserted my cock into her pussy and leaned forward so I could suck on her tantalizingly erect nipples. I moved my legs together and Jamie did the same with hers, which allowed Robby to climb aboard and straddle the two of us. He squirted some lube onto his index finger and worked it into Jamie's rear hole, removed it quickly, and leaned forward while pressing his cock's head against her anus. She balanced on one hand above me while reaching back with her other hand and pulling her butt cheek aside to provide him greater access. A deep grunt from her, plus added pressure on my dick inside her pussy, told me he was in her ass. I lay still with my hands on Jamie's hips while Robby did all the work. He pounded her ass with enthusiasm and some deep penetration while she ground my pussy against my lower body. I saw Jamie's chest flushing red and moved my hands from her hips to her tits, tugging insistently on her nipples to match the rhythm the two of them were playing out above me. After a couple of minutes, Jamie let out a big groan and announced she was cumming.

By this point Robby was starting to run out of gas, so he pulled out of her ass and stepped across the hall into the bathroom so he could find a towel for wiping off his dick. Jamie rolled off me and onto her back, but she was clearly far from done. Neither was I -- so I climbed off at the foot of the bed and pulled Jamie toward the edge, pushed her legs up into the air and told her to hold them there (which she did by looping her arms around the backs of her knees), and then I sank my cock into her ass. It was the first time I'd done anal in probably 20 years, and it felt terrific. I was soon pounding her with balls-deep thrusts, and she let go of one leg so she could reach down and mash her fingers against her clit in a rapid-fire manner. Meanwhile, Robby crouched next to her face and stuck his newly cleaned-off dick into her mouth. She sucked him enthusiastically while I fucked her ass; then her butt muscles clenched and she was suddenly in the midst of her second orgasm.

Once it passed I withdrew, especially since my legs were shaky from all the thrusting that I was hardly used to anymore. Robby decided he wanted some more of Jamie's asshole, so we switched positions and he stood at the foot of the bed with his dick inserted all the way into her poop-chute. After about eight or ten thrusts he announced he was ready to cum, so he pulled out and shot a nice thick glob of white goo all over her pussy lips, with some coming to rest on her shorts. I was positioned behind her, with her head cradled in my lap, so I reached down and used two of my fingers to scoop up some of Robby's ejaculate. Then I popped my fingers into Jamie's mouth and she sucked them dry.

By now it was time for Robby to split, but I wasn't quite ready to call it quits and Jamie agreed to let me take her home. As Robby dug around on the floor for his discarded clothes and started to put them on, I finally pulled off Jamie's blindfold -- it was simply too much in the way after all this time -- and convinced her to get on top of me, 69-style. Robby said a quick goodbye, to which Jamie was only able to reply with a muffled grunt, since at that moment she had my entire cock in her mouth. I licked her pussy, sucked on her clit and slipped a finger into her ass, hoping to induce a third orgasm, but she came off my cock long enough to explain we'd made her pretty sore down there, so instead I pulled my face and hands away from her crotch and simply let her do her work. About three minutes into this latest activity I said, "OK, finish me off." Jamie took that as a cue to get me to cum, so she wrapped her hand around the base of my cock, sucked harder on the head, and shortly thereafter I was pumping my jizz down her throat.

She wanted to smoke a cigarette (Marlboro!), so she slipped on her black lace top and I led her toward the deck that's just outside our back door. She also wanted something alcoholic to drink, so I unscrewed the top off a tiny bottle of Barefoot Moscato and poured it into a juice glass. Classy presentation, eh? By now it was nearly 2:30, so rather than begin another fuck session -- we were both pretty sore at this point -- I suggested I drive her home. We got dressed and hit the road. On the way there, we enjoyed an interesting conversation about local politics, the police -- she was on probation for her 2nd DUI, thus a suspended drivers' license and the inability to drive -- and other non-sexual elements. As she exited my car she stuck her head back inside and gave me a warm kiss on the lips. "Tell Robby I'll be in touch again soon, OK? And next time, a couple additional guys would be all right." She'd obviously enjoyed herself!

I finally had my first anal experience.

I am seeing this married woman for almost a year, it is a thing from work, that escalated to FWB situation. She is a beautiful woman, little bottom heavy, but still very, very good looking for a 40 year old.

We fuck once or twice a week, and this is an arrangement I am totally happy with. Now, the confession part is, that last week, we had sex, she had already came when we switched to spooning position. I kind of separated, if you understand what I mean, to enjoy the view of coming in and out of her, so I was going all the way in and all the way out, she was wet that much, that her thighs were all sticky. I was doing this slowly, and she loved it, and one time that I was going back in, I kind of missed, and pressed against her asshole. I did back out immediately, but she reacted with a loud moan. So I pressed against her, kissing her neck, now trying to "miss" on purpose. And I did, and loved her reaction. Everything was so wet, that when on the fourth or fifth "miss" I pressed, and did not back out, it just went in.

She moaned loudly, and turned to kiss me, eating my face from lust. I managed only three more strokes and finished inside.

After the shower, I asked her if she enjoyed it, and she said yes, admitting that she had no idea that she might enjoy such a thing.

I am seeing her Monday after work, and I think I just struck gold.

How It Started 3 1 and 2 were posted earlier
After Jack left I jumped up and got in the shower. It was Saturday and I didn’t have to work until Monday. I thought I had better hurry before Jack gets impatient and starts to get angry. I had grabbed a razor and some shaving cream before I got in the shower. I have been shaving my private areas for a couple of month now. I didn’t have very thick hair on my arms or legs and I had never had much facial hair. I only shaved maybe once a week and only because it looked straggly. I shaved my legs and what few hairs I had on my chest. I made sure my ass and front side was smooth. The plug was still in my ass when I got ready to shave there so, I had to pull it out, shave and then put it back in. My body felt strange when I got out of the shower. It was cool and tingly. I went to the mirror and started doing my hair. I was trying to curl it while I was blow drying it and it sound funny but, it was looking pretty good. I put on some make up to help me look more like a girl. When I got done I went to get something to wear. I didn’t have a lot of clothes to wear. Mostly what I had were panties, sleepwear, and a couple outfits. I never needed much because I only wore them in my room. I put on a thong and found a pair of shorts that were really tight and short. I remembered I had bought a halter top when I bought those shorts. Then I heard Jack say “Come on Sue. We don’t have all fucking day.” He was mad, so I hurried up and put on the shirt I had on last night and tied it over my stomach. Then I thought “OH FUCK. I had forgotten my chastity device.” I got it out of the drawer and put it on my dick. I clicked the lock and didn’t know what to do with the key. I stuck it in my pocket and ran downstairs.
When I got downstairs, Jack was in the kitchen. I said “I’m sorry for taking too long.” Jack looked me up and down. He said “You are worse than a woman. Did you wear everything I told you to?” I nodded yes. “Well let’s see.” He replied. I unbuttoned the front of my shorts and turned around. I pulled them down over my ass and bent over. I reached back and spread my ass cheeks so, he could see the pink jewel on the end of the plug. He walked over and rubbed my ass. Jack grabbed the end of the plug and started to pull it out. The fat part the plug slipped out of my ass and he pushed it back in. I moaned when he did it. Jack said “You like that sissy don’t you. Now turn around and show me what else you got on.” I stood up and turned around. He snickered when he saw the lock and said “That’s nice. Where’s the key?” I reached down and got the key out of my pocket. I handed it to him with my hand shaking so much I almost dropped it. Jack said “Is that the only one?” I nodded yes and Jack smacked me a crossed my face hard. He said “Don’t lie to me. Is this the only key?” My eyes watered up as I shook my head no. He told me to go get the rest of them. I ran to my room and got the other two keys. I went back to the kitchen to where Jack was standing and put my hand out with the keys. He took the keys and said “This better be all of them or you will be sorry.” I blurted out “I’m already sorry.” And he just laughed.
“Come on Sue.” He said “Were going for a ride.” My eyes got wide with fear. I had never been out of the house dressed like this. I said “Please Jack no. I don’t want to leave. I’ll be good and do anything you want. Just don’t make me be seen like this.” Jack said “It will be ok. You look great and where we’re going nobody will see you.” I was kind of flattered that he thought I looked good but, was scared of where he was taking me. He grabbed my arm and started pulling me towards the door. We got to the driveway and he told me to get in his truck. I got in the passenger side and he started to back out when he said “Slide over here next to me.” I slid over and it looked like I was his girlfriend on a date. We didn’t drive far before he was reaching in his pants and pulling his cock out. I looked down and knew what he wanted me to do. I slid down the seat and turned so that I was facing his lap. I lowered my mouth until it was just above his cock and he pushed the back of my head down on his cock. I bobbed my head up and down sucking him. We were going down the highway with me sucking him the best I could when I heard a horn blow. I never stopped but Jack laughed and said “I think the truckers like you. Get back on the seat with your knees pulled up.” I never stopped sucking his cock as I climbed back on the seat and put my knees under my body. My mouth was on his cock and my ass was up pointing towards the passenger window. I didn’t look back not wanting to see who was going to see me. Jack told me to take my shorts and thong off. I shook my head no with his cock in my mouth. He grabbed the hair on the back of my head and shoved me down until his cock was all the way down my throat. I couldn’t breathe this way and he knew it. Then Jack said “Do it and I will let go.” I couldn’t get my shorts off fast enough and when I did he released my hair. Now my ass was bare and facing the window for everybody to see. Jack loved it. He would speed up to catch some trucks and then slow down when we were beside them. He did this a couple of times and then told me to reach back and pull my plug out. I did as I was told and the he said “Start fucking your ass with that thing until I tell you to stop.” The plug would stretch my asshole when the fat part went in and out. I was still sucking his cock and every time the large part would pass though me, I would be forced to take a deep breath causing me to suck him deeper in to my throat. He rolled the window down and I could hear horns blowing and I thought I heard people hollering something. This went on for a while and then Jack rolled the window up. He told me to sit up and put my shorts back on.
I got turned around and when I looked up I saw that we were pulling into a mall parking lot. I was scared as hell, not knowing what Jack was doing. He said “We are going shopping. You need some new things to wear.” I was scared. I had never been in public dressed as a girl. I had fantasized about it but, never had the courage to do it. He parked the truck and got out and said “Come on lets go.” I just sat there and refused to get out and Jack said “Sue, you better do what I say or I will take you to that truck stop on the highway and let all the truckers that you just flashed fuck you until can’t walk!” I knew I had to do what he said so; I got out and walked into the mall with him holding my arm really tight. Our first stop was Victoria Secrets. Jack was picking up lacy thongs and sleepwear. Then he turns and said “You need some bras. What size do we get? Double A-.” and laughed. He called a sales woman over and asked where they kept the bras that would fit his girlfriend. It was funny I almost smiled when I thought about him calling me his girlfriend. She pointed to the area of the store to go. He found some bras that were for flat cheated women. He handed me several and then he saw the garter and stocking. He like them and grabbed a few of them. My arms were full of things and he walked me to the checkout. I put the stuff on the counter and the girl scanned them. It was over $400 of stuff. I looked at Jack and he bent down and whispered to me “You better get your credit card out before I start sending your pics to my friends.” I paid for the thing and we left the store. The rest of the day was more of the same. We want into a lot of store and bought more clothes. Everything he picked out was slutty clothes that a prostitute might wear. He even made me but heels and boots at a shoe store.
We were walking down the mall and I was amazed that all day nobody seemed to know I was a guy. I even had seen a few guys checking me out like I was girl. Then all of a sudden I saw a group of guys that I had seen before. They were friends of Jack and John for the gym or the bars. I never looked up and just walked by them. Jack stopped to talk to them. I walked down the mall and thought I better stop and wait. After a few minutes Jack walked up and grabbed the back of my neck and said “Don’t you ever walk away from me? You should have stopped and chatted with the guys that will be fucking you soon!” I didn’t know what to say but, “I’m sorry” Was he really going to make me fuck all his friends? Maybe he was just threatening me. Then he said “You owe me for that and I know how make you pay.” I guess we were done at the mall because he led me out to his truck and we started to drive.
We drove for awhile to a place I was not familiar with. It was a part of town that was run down and an area that most normal people go. There were vacant building everywhere and a few people that looked like they were wondering around. Jack pulled the truck over and said “Get out! I want you to get out of the truck and walk down this street. I’ll pick you up in three blocks if you make it that far. All you got to do is anyone you pass you got to ask them if you can suck their cock! If they want you to you got to go with them and do as they say. Suck them; fuck them or whatever it takes to get them to cum on or in you.” I panicked and pleaded Jack not to make me do this. I told him I would do anything he asked just please take me home. He said “Tell me what you will do to make this not happen.” I started blurting out that I would suck his cock anytime he wanted and he could fuck my ass as often as he liked and I would be a good slut for him. He said “OK only two blocks then.” I screamed “NOOO, I’ll dress like a whore and you can show me off to anybody you like. I will act like a slut and you can take me anywhere you want and show me off to your friends.” Jack said “Just one block unless you got more to offer.” I thought and then whimpered “I will suck and fuck all of you friends and I will be your whore to use. Please don’t make me walk down this street.”
Jack said that he would agree to this if I proved that I was a good whore. He said “Pick someone on this street and suck their cock and we could go home.” I didn’t have a choice and it was better than having to walk three blocks and have sex with everyone on the street. I looked around and pointed to an old bum that was sleeping in a doorway. I figured he probably not interested. Jack pulled the truck next to the doorway and rolled down my window. Jack said “Go ahead and ask him.” I called out to the man and he just grunted. I yelled again and he rolled over and I seen his face. In the doorway he was all balled up but, when he looked up I saw he was a black man. “Tell him” Jack said. I said “Sir, Do you want me to suck your dick? I will if you want me too. He got up and started to walk towards the truck and Jack said “Show him your ass.” I turned around and put my ass up toward the window. I pulled my shorts down over my ass just as he got to the truck window. He was looking at my ass and Jack asked him if he wanted to get in. I heard the door open and I moved over to let him in. He got in the truck without saying anything. Jack said “Ask him again.” I asked him if he wanted me to suck his cock and then he started reaching in his pants. He unbuttoned and unzipped his pants and pulled out the biggest fucking cock I had ever seen. Jack started laughing and said “Good choice Sue.” His cock looked more like an arm than a cock. It was at least a foot long and as big around as a beer bottle. I knew there was no way I could suck his dick. Jack started to drive and told me to get busy. I crawled down to the floor in between the bums legs and put my face in front of his cock. I reached to the side of the seat and moved it as far back as it would go. This gave me room to move around and kneel in front of him. He smelled terrible. He smelled like burnt wood and strong body odor. I started licking his cock and it tasted just as bad as it smelled. I tried spitting on it a lot to help the taste, but it only helped a little bit. He was getting hard and thank god it didn’t get much bigger. I was licking up and down his cock and he was moaning. I put the head of his cock and tried to take him in my mouth. I was only able to get a couple of inches in and my mouth was full. Jack must have thought I wasn’t trying hard enough because he grabbed the back of my head and started pushing me down. Even with him pushing, it wouldn’t go down my throat. I only had less than half of his cock in me. The bum was starting to breathe heavy and was moaning. Jack pulled my head back and said “Not to fast Sue. Don’t make him cum yet. I want to see how much of that monster you can take in your sissy ass.” I pleaded with Jack not to make me do that. I knew his cock would hurt me and probably give me some sort of STD. Jack didn’t want to hear it. “We can go back and you can fuck all the men in that area if you want.” Jack said. I told him that I didn’t want to do that either. He said “It your choice.” I knew I would lose. I lost the last night. I lost this morning and I’m going to lose now.
I got up without saying a word or looking at either one of them I got up and pulled down my shorts and thong down. Jack said “Bend over and let your lover pull that thing out of your ass.” I leaned towards Jack and put my ass up towards the bum. He looked at my ass for a while with a confused look on his face. Then I thought “Oh fuck, he thought I was a girl.” He reached out and touched my ass and I cringed. He spread my ass cheeks and was looking at my bottom with a pink jewel in it. He grabbed the plug and started pulling like he didn’t knew what it was. He kept pulling harder watching my ass stretch around it until in came out. He looked at the plug and then I saw him put it his pocket. I remember thinking it was kind of funny. He must have thought the jewel was worth something. I got back up and moved until I was sitting on his lap. I rose up until I could point his cock at my asshole. I sat back down and started putting pressure on it to push it in. It felt like I was sitting on a pole. It wasn’t going in at all. I pushed back as hard as I could and it never went in anymore. I looked at Jack and said “It’s not going to fit.” Jack told me to look in the glove box. I opened it and saw some condoms and some gel. I grabbed the condoms and Jack hollered “No slut, use the gel.” I squirted some of the gel on my hand and reached back to put it on his cock. I thought I better use a lot and put more in my hand to spread on my asshole. I got back up and put his cock back to the entrance of my ass and pushed. “OH FUCK” I squealed. Only the head of his cock went in me. It felt so big and burned as my ass tried to stretch around it. It still only went in an inch or so and stopped. I would push back but, my ass won’t open for it.
Then all of a sudden we hit a big bump in the road. The jolt slammed me down on his cock and another couple of inches went in me. I screamed like I stabbed and was not able to breathe. The pain was terrible. I was trying to maintain my balance while I got used to the size of his cock. Jack saw what the bump did and must have got an idea. He started giving the truck gas which pushed my back towards the bum’s cock. Then he would slow up and then give the truck gas again. This made me moved back and forth on the bum’s cock. Another inch slide in me and I was holding on the dash trying to control. All of a sudden Jack turned down a street and I recognized the area. We were back at the mall. I thought “Oh no, everybody was going to see me.” That was not why Jack came here. The mall was big and had a road that circled it. When we hit the first speed bump I knew why Jack came here. The bum’s cock slammed another inch in me. The mall road had a lot of big speed bumps on it to keep people from speeding. I was doing my best to hold on to keep control when Jack said “Put your hands on your head Sue.” I knew that meant there would be nothing stopping that cock from going all the way in me. I let go of the dash and put my hands on my head when the next bump hit. His cock slammed into me and I think I almost blacked out. I pushed with my legs trying to lift myself some and the next bump came. More and more of the bum’s cock was going deeper into my ass. The speed bumps seemed to be very close together and my legs were tired and I couldn’t lift myself anymore. Every bump pushed his cock farther in me. My ass didn’t hurt much now but, I felt a lot of pressure on my insides. My weight forcing down and the speed bumps slamming me on his cock must have pushed the bum over the edge. He grabbed me around the waist and pulled me down hard on his cock. I felt his cock drive deeper than ever and I felt his course hair rub against my ass. He was all the way inside me. My stomach felt like I had been punched in it. He grunted as he came in my ass and then he released me. I was too weak to lift myself off his cock and just sat there impale by his big cock.
Jack reached over and grabbed me by the arm and pulled me towards him. The bum’s cock was yanked out of my ass and Jack said “Funs over get the fuck out dirt bag. Get the fuck out.” The bum never said a word and just stuffed his cock into his pants and opened the truck door. As soon as he was out Jack sped off. He looked at me and said “What a slut you turned out to be. Time to go home sissy.”

Hello all you dirty kinky perverts. I have a confession and I can only tell you all because none of my friends and family would like it, I am still not sure I do but it happened and there is nothing I can do about that now.
Ok my name is Ann and I am 39 years old, I left my husband about 4 months ago, he was very abusive both verbal and physical. I had to move over 400 miles away to get away from him. It was an old friend from school who actually convinced me to leave him. We reconnected through facebook about a year ago. And in that time I opened up to her about what was happening in my life. She always said I could come and stay with her if I needed to get away and I finally took the plunge packed a few bags left my husband a note and left, got on a train and turned up at Lisa's door that same day. She welcomed me and it was like we had never been apart, we had always been close at school until she moved away when her dad got a job. She had gone through something like me and had got away from her abusive husband, but unlike me she had 2 daughters Jan 21 and Laura 19. She was much stronger that I was and took her husband to court and he is actually serving time. That first night we just sat and talked drank a lot of wine and she told me she was seeing someone, what I didn't expect was she was seeing another woman and said I would meet her later in the week. She showed me to the spare room and I was very drunk at that point, I woke the next morning with a bad hangover laying on top of the bed totally naked. I couldn't remember getting undressed but I needed to pee so very much I ran to the toilet still naked burst into the bathroom and sat down to pee. It was only then that I saw Lisa in the shower, I laughed and said I was sorry but really needed to pee. The bathroom was a full on wet room with no shower screen and I got a very good look at her naked body, and thinking back she got a good look at me too. Now about the only good thing my Ex did for me was making sure I kept myself fit. I am quite short just 5 foot tall, I have long dark hair but very small almost no breasts at all. For 10 years I have waxed my pussy and don't think I will ever let hair grow back now. As I looked at Lisa, feelings of jealousy came back because unlike me she has and always had massive breasts and also unlike me she had a nice pubic bush, he strawberry blonde hair looked amazing next to her pale skin. She also has freckles all over. I remember seeing her naked as we were growing up but couldn't remember all those freckles, I asked her where they all came from and she laughed saying she always gets more every time she sunbathes. I finished peeing and said I should go put something on, she laughed and said not to worry about it as she and her daughters really didn't bother too much with clothes at home. I stood up and she said to come and shower and she would was my back and hair for me. She was so gentle and I almost didn't notice as she got lower and washed my bottom too. We dried off and she said I should come and meet her girls. I had a towel on but when we got to the kitchen both her girls were totally naked and oldest Jan was her double. Laura was short like me and a natural blonde, She was in a word beautiful.

Now as the weeks went on I got very used to being naked with them all, and Kerry, Lisa's girlfriend was so nice I could see why she liked her. Last month Lisa had to go away on a course and left me alone with the girls. Jan had gone out and I went to ask Laura what she wanted for dinner, her room door was wide open and she was on her PC, there was no mistaking what she was looking at, it was a lesbian porn movie and there was also no mistaking what she was doing, she had a vibrator deep inside her pussy, I didn't know what to do or say, but she laughed and said sorry she forgot to close the door, all the while sliding her vibrator in and out her pussy. She turned round and I got an even better view of what she was doing, her legs wide open and shaved pussy it looked amazing. Now I had never ever been with another woman before but had thought about it and more so since I started living here. Laura laughed and asked If I liked what I saw? Before I could answer she reached out and put her hand on my pussy, she smiled and said "your wet" All I could say was what do you want for dinner? she pushed a finger in my pussy and said "your pussy" I was lost from that moment on, she pushed me onto her bed opened my legs and before I could say no she was licking my pussy. I gave in and let her do what she wanted. I have to say her tongue was amazing, I knew she had done this before, maybe lots more. I came soon after and she kept licking and I came again and again. She finally stopped and said she had wanted me from the first time she saw me. I told her I felt so guilty but she laughed and said not to. I went to make dinner and I felt her behind me, she kissed the back of my neck her hand at my ass, she pushed her finger at my asshole and then pushed it in, I am very used to anal sex as my ex would fuck my ass most nights and if I am honest I enjoyed anal more than in my pussy. She had me bent over the worktop and she was fingering my ass, now she was quite rough too and spanked my ass too, she called me her whore and said I would have to do what ever she wanted now. She kept spanking me, quite hard and I knew it would be sore to sit after this. She pulled her fingers from my ass and put them to my mouth and told me to lick them clean, I did as she asked and then she turned me round and kissed me. Now the next 2 weeks she would come to my room at night and do what ever she wanted to me. We almost got caught by her sister a few times.

I moved out last week into a small flat just down the road. Laura visits me each day and uses me like a whore. I am so scared Laura will find out

I proudly confess, I turned my buddies 26 yr old daughter into a cum sponge ! and I am wearing her cum soaked panties as I tell you this , I was visiting my friend, who lives about 100 miles away, he asked if I would take a phone back home with me, and his 26 yr old daughter would come get it , she lives close to me, her face and body popped in my memory right away, sure ill take it .. well i was home maybe 30 min, when she calls, asking if I wanted to meet her , or she could come to my house, i gave her directions then sat down with a scotch to wait. when she came in, she was much prettier than I remembered, and nice full, round firm tits that she displayed in a super tight, low cut tank top, man, no freaking bra on.. I had been rubbing my cock, before and when she arrived, so when I stood up, so did my cock, she acted as if nothing happened, nothing did, except me showing my erection to my friends young daughter.. I asked if she wanted something to drink? wine she tells me, my mind was racing, my lust for this young girl was raging, I opened the best bottle I had, knowing how a Good wine makes one feel, I have a chance of having a dream come true.. Gawd this babydoll is so fine...she sipped the wine, I looked at her ,there it was the slight skin flush of warmth, nipples staying hard , ,great .we talked, I glanced boldly at her breasts and between her legs as we spoke, I gave her $20 and said her dad asked me to give it to her, I knew she was having a hard time, so I said , next time you are in a tuff spot, u got my number, call me, if I can help, if I can do Anything for you, call me looking, at her tits again, slowly I raised my eyes to look into hers, if I can help you, I will help you , thanks she replied.. I lit up some refer took a drag then offered it to my guest, I turned up the stereo her eyes closed as she moved with the beat coming from the speakers, going for it , I stood up reaching for her hands , I said dance with me, that hard body melted into mine, her breasts were mashed against my chest, the light shorts she wore couldn't hide the wetness between her legs as I ground my hard on all over her body, she was loving it, I was loving it , she looked into my eyes and smiled wickedly, as she turned around, pressing her pretty ass up to my cock, as we moved to the music I started fingering her clit and feeling those fantastic breasts of hers... i pinched ..one nipple a little too hard, she yelped letting me know, and almost at the same time her body contracted and fluid gushed from her pussy, I mean, she must have squirted 2-3 gallons, she was weak, so I helped her to my bed, to relax.. let me get these wet things off you pulling her shorts and panties off, as soon as they cleared her feet, I buried my face between her legs, double licking her twat and taking in the womanly scent that comes from between her legs, smelling that woman hole my cock turned to rock Hard Cock, and I was like a dog humping her fucking leg ! I couldn't pull my mouth away from her pussy, , I ravaged that hole, that, tight cunt, that hot, tight, wet pussy.. I pulled her bottom up towards me, and I pulled back my head, there was her shaved cunt, and asshole at eye, and mouth level, my tongue darted to that little brown hole, I licked around it, this way and that way then pulled her ass cheeks apart,. my tongue went straight into her asshole! as I tongue fucked her, Gawd, she moaned, she shot gallons of cum all over both us and my bed. I held her clit in between two fingers and I put two more fingers up her butt hole. I want to feel my cock down your throat I said, getting up on my knees,she took it all down to, my balls, she throat fucked me for a while, then she stopped she stood up, looking down at me she says as she straddled my face, you are going to worship me , you are going to call me your goddess, she ground her sweet wet pussy into my mouth, do you want to worship me little man , yes i nodded, good she said as she grabbed my cock and guided it to her sweet asshole.I am with her almost 24/7 now, and I cater to her, I lick her, I worship her, she lets me lay at her feet and suck her toes when her g.f.s come to visit...oh I forgot the amazing thing here, I'm 64 shes 26. you know how many times 64 goes into 26? as many times as it can ...lol

I confess that I had my first sexual experience with another man last night.

I've fantasized about being with a guy for a long time. I'm not attracted to other men, but the idea of sucking another guy's dick, having a man finger my butt or even having a guy fuck me in the ass has always turned me on. I've bought toys - dildos, buttplugs, prostate massagers, etc - used them on myself and had some amazing orgasms...but I'd always be fantasizing about a real dick sliding up my ass.

After a going through a recent sexual drought, I finally decided to get over my shyness and fulfill my fantasy. I responded to a couple of interesting ads on Craigslist and found a guy who sounded decent and was interested in some of the same things I wanted to try. We corresponded a bit, then agreed to meet up in public and get a hotel room for the night to fool around. He was about 10 years older than me (mid-40s), slightly overweight, average height and a bear; he seemed decent during our brief public conversation and we discreetly got a room.

There was little conversation once we got in the hotel room, as we both quickly stripped and got things started. Neither of us was into kissing or embracing or anything like that, just looking for sex. I'd indicated in our correspondence that I was looking to bottom and be more submissive, while he was interested in being more dominant. He sat down on the bed and I got down on my knees in front of him, with his cock in my face. Prior to this, I'd never had a close look at another guy's dick. His cock was average length (five to six inches) and slightly thicker than mine, while his bush and balls were unshaven. I cupped his balls with one hand and started stroking the base of his shaft with the other, then finally slid the head of his cock into my mouth. I didn't try taking it very deep, as I have a hell of a gag reflex, just sliding it in and out a little and running my tongue around the head and along the underside. I'd pretended to give blowjobs on my dildos before, but this was totally different. The taste of his cock, how it felt in my mouth, his balls in my hand...incredible. From his groans, he was clearly enjoying it. After awhile, I felt his cock throb and the head flare in my mouth - at first, only once every couple of seconds, then more frequently - and I got my first taste of his old-cum. At that point, he told me to sit on my hands and just use my mouth. I obliged and focused just on sucking him, until he put his hand gently on the back of my head and his cock began to pulse. I've eaten my own cum before, but having a load shot directly into my mouth was entirely different. Usually, by the time I'd get my own jizz in my mouth, it would have cooled and started to become clumpy. His load was a spurt of warm liquid directly onto my tongue and down my throat. Each time his dick would pulse, another burst of sperm would flood my mouth and I think he shot five spurts before he was finished. He told me to keep his dick in my mouth and suck out the remaining cum until he went soft, then had me kiss each of his balls and thank him for the jizz.

He told me we had some time until he was hard again and that he'd use it to prepare my virgin ass. By this point, my dick was throbbing and I desperately wanted to cum, but he told me I wasn't allowed to yet. He instead had me get up and bend over a small table in the room. He then put on a set of latex gloves, spread my ass cheeks and told me to keep my eyes forward. I did and soon felt a cool fluid applied to my asshole and the surrounding area. He began to rub my hole with a well-lubed finger, slowly, in a circular motion and gradually applying more pressure. I tried to relax as much as possible as he slowly pushed the tip of his finger through my outer sphincter and continued his slow massaging of the inner ring of my asshole. During my solo play sessions, I've fingered my own ass, but the sensations of having another man sliding his finger slowly up my butt was entirely different. On my own, I could control the speed, depth and pressure of the movement, but here I had to just accept his movements. Finally, my anus yielded and his index finger was inside me. The slight pressure in my butt felt good and I enjoyed it for a few moments before he began to stroke my insides, the beckoning motion of his finger searching for my g-spot. When he finally found it, the sensation was incredible. My urge to cum shot up as pulses of intense pleasure went through my dick with every motion of his finger. The feeling was so much more intense than any of my attempts at massaging my own prostate. I couldn't decide what I wanted more - to cum or to have him fuck me. I think I begged for both at one point. Buried in the pleasure was a feeling of increased pressure on my asshole as he started to work his middle finger into my ass. With both of his fingers inside me finally, my butthole started to hurt a bit, but I forgot about that as he intensified the prostate massage, using both fingers. I pleaded for him to milk me, to jerk me off and let me cum, but he still refused. It wasn't time for that yet...it was time for him to fuck me.

Keeping his fingers up my ass and me bent over the table, he presented me with a condom and made me unwrap it and slide it over his stiff cock. I kissed his balls again, at his request, then he had me apply lube to his sheathed cock. Finally, he withdrew his fingers from my hole, took off the glove and positioned himself behind me. He pressed the head of his cock against my asshole gently at first, then increasing the pressure until my anus spread for him. As he pushed in, I relaxed and pushed back against him - within a few seconds, he was inside me. I'd put dildos up my ass before, but this was a completely different experience. His cock was warm and moved inside me as he shifted position; it felt like he was so deep up my ass and his girth stretched my anus even further. I could feel his bush against my ass cheeks and his balls against my upper thighs. After giving me a few seconds to adjust, he started to fuck me. He started slow at first, drawing his cock most of the way out, then sliding it all the way back in slowly. His strokes would catch my prostate on occasion and I couldn't help but moan as ecstasy shot through my dick. He changed up his thrusts, pulling out maybe an inch, then pumping back in, keeping his cock deep inside of my rectum. After a few minutes, he pulled his cock out most of the way, staying inside me only an inch and doing shallow thrusts, which felt so good on my prostate. Once I'd relaxed enough, he withdrew his cock completely, allowed my ass to close a little, then thrust back deep inside me. The first time he did this, I moaned especially loud and begged for more - after that, each time he withdrew, he told me to beg before he'd put it back in again. And I did. Over and over. He then thrust deep into me, laid on top of me on the table and began to thrust more rapidly - deep, hard, fast pounding of my asshole. His breath quickened in time with his thrusts and it felt like his cock was swelling inside me. With a final groan, he shoved his dick as deep in me as he could - I could feel him pulse even through the condom and knew he was cumming, finally cumming after almost 15 minutes inside my butt.

He withdrew his dick from my tired asshole, took off the condom and laid down on the bed, then beckoned me over. He had me straddle his thighs and then he began to finally stroke my dick. I came in less than 10 seconds, my throbbing cock finally getting release. I pumped out more jizz than I think I ever have in my life and he made sure it all ended up on his dick and balls. When I was done, he squeezed the contents of the condom out onto his cock, mixing our loads, and had me lick him clean. I was still shaking and weak from the intense orgasm and thorough fucking, but did as he said and cleaned up all the cum from his body. With that completed, we both dressed and left.

My writing may not convey it as well as I might like, but it was an amazing experience. I've never felt such intense pleasure, never thought it would feel so good to be fucked in the ass and never cum so hard. He's already sent me a message suggesting we do it again, though he'd like me to show up with a buttplug in next time, so my ass is already prepared and he can just pull my pants down and pound me. He's also suggested maybe bringing a few other toys or even having a longer meet-up, so he can give me a real prostate massage and spend a few hours with his cock in my ass. I'm already looking forward to it.

Today my sister came over and said she has not had any  cock since the pandemic! Proceeds to drop her shorts bends over my couch and says have at big brother! I stood there in disbelief! Walked over spread those apple bottom cheeks and dove in head first licking that pussy and asshole! She is moaning and bucking and exploding! I get up after 20 minutes and put the head of my cock to that beautiful pussy and she bucks back! I am balls deep in my 22 year old sisters pussy! She is moaning, screaming and exploding! I let a big grunt out and just explode in her! I mean I filled her! Cum is just dripping out the more I fuck her and after about 15 minutes I explode again and now it is running out down her thighs she says I am done and omg my pussy thanks you! She drops to her knees starts to suck my cock clean I start to get hard she continues to suck my cock and now I am rock hard she continues and she can tell I am about to cum! She starts jerking me off and I start cumming and she just starts licking and swallowing! 

Part 6: Last day of skiing

Part1:http://mlos.pika777.eu.org/V3167386
Part2:http://mlos.pika777.eu.org/V281D41F
Part3:http://mlos.pika777.eu.org/V864472F
Part4:http://mlos.pika777.eu.org/V894B84B
Part5:http://mlos.pika777.eu.org/VC75358A

After I left the Sauna/Spa and went up to my room, I heard what kind of reward Mike got for playing the alpha male. That faint squeaking noise again. When Mike and Jolie got down to dinner, I was already there. She wore a wonderful dress again, with a little push up for her breasts. It was dark green, in perfect contrast to her hair. I cant really point a finger at it, but she looked like she just had sex. When I got close to her when she was at the salad buffet, I could even smell it. I guess it was the estrogene coming from her body. I got aroused and frustrated. I hadnt had my chance today. And I couldnt get any closer now. I finished my meal without seeing her again or being close to her. My frustration only got worse when I went to my room. I listend for them to come up too. When they came and passed, I went to my door to see if she slipped anything through this time. Nothing. I watched TV, read my book. Nothing would help. So I went to bed. When I was already half a sleep, I heard my phone vibrate. I looked at the clock. 11 pm. It was Jolie. I sat up immediately and was wide awake.
J: "I'm sorry, Mike was so protective of me. He would have recognized you if you came too close. I can chat now though, he is fast asleep."
Me:"It's okay. You looked beautiful at dinner tonight."
J: "Thanks! I was worried that my hair was messed up because I fucked Mike just before dinner."
Me:"I heard that. Your hair was fine."
J: "I'm sorry you must be frustrated, not a good topic to talk about that then. Just one more thing: Mike fell asleep so quickly, he didnt get me after dinner... I still need pleasure though..."
Me:"I have a spot for you right next to me... ;-)"
J: "I cant, its too dangerous. After last time, Mike was so suspicious."
Me:"Damn shame. Tomorrow is the last day for me..."
J: "For us too..."
- Pause -
Me:"I want to see you once more. I want to fuck you. Make you my slut."
J: "I would like that... but I dont see how... You make me wet..."
- Jolie sent a pic of her wet pussy -
- I sent a pic of my dick -
Me:"Send one with mike sleeping besides you on it"
- she did -
J: "You like that?"
Me:"Yeah I like it if you're my little slut..."

We continued chatting and exchanging pics for a while. She made me promise not to show any of those to anyone. And I only broke that rule for Anna (see my other stories). I told her I would try to follow them the next day and she agreed.
The next morning went by without anything interesting happening. I followed Mike and Jolie to the gondola as before, but this time I got into the cabin with them. It was a risk, but I felt like it. Jolie looked at me in panic, before trying to look relaxed. Mike didnt recognize me at first, but then said "Hey, dont I know you?" - my heart stopped for a moment - "You are a guest in the same hotel as we are!" "Oh yes! I think I saw you in the sauna the other day." Mike:"I hope you didnt stare at my fianceé like that old dude." He laughed. I laughed with him "No I didnt even had the chance. You left just as I came." Mike:"Right, right. So are you here on your own?" Me:"Yes, but I met nice people in the hotel." Mike:"Yeah? Who?" I looked at Jolie for a brief moment. She seemed tense. She hadnt talked at all. Me:"Well you know the cute receptionist?" Mike:"No way really? Nice bro." Me:"Thanks" even though I wasnt sure what he complimented me on. I barely suggested anything. We went silence for a little bit. When we arrived at the top, Mike asked me if I wanted to come with them. I agreed, even though Jolie looked scared. So we went down a few pistes, but after a while Mike said:"I wanted seen this black piste over at the other side, wanna join me?" Jolie answered:"You know I dont like black ones, they are too hard for me." I said:"Yeah, I'm not that good at snowboarding yet." Mike:"Okay you suckers can stay on the red piste all you want, I will try the black one. Lets meet here again in 20 min okay?" Without waiting for our answer, he went his way. We looked at each other. Smiled. We went down the piste half way, before turning into the forest once more. Once again she sucked me off, but she had to make it quick so it wasnt that much of a pleasure. I gave her a good mouth full anyway. We quickly went down the rest of the piste. The lift was only half filled when we left the bottom station. Jolie was sitting to the right of me, at the right-most seat. I leaned forward a bit, got out of my gloves and shoved my hand in her pants. My body should cover the view. She inhaled sharply. My fingers found her clit. I already felt her wetness. I played with her clit until we were close to the top station. Shortly before we arrived I told her "Get down from the mountain at 12:30 today." She looked at me in confusion, but didnt answer since we arrived and Mike was already waiting. When we reached him I said "It was nice skiing with you, but I wanna go solo for the rest of the day." Mike nodded "I get it man. Have fun!" I nodded and went my way. I made sure to be at the gondolas top station way before 12:30 so Mike wouldnt see me arrive. A little before the agreed time, Jolie arrived. We got into a cabin, I asked: "What did Mike say?" Jolie:"He wants to get as much as possible out of today." Me:"Well thats something we have in common." She smiled. While we went down hill it started snowing. Jolie sat besides me and my hand was in her pants again. She leaned against me as I fingered her pussy. Her soft moans were a pleasure for my ears. Shorty before the bottom station I managed to make her cum. She hugged me and said "Thank you. Thank you for everything." We got out of the cabin and I said "I'm not done yet. Come to my room right away, when you get into the hotel. Jolie:"But... What about Mike?" Me:" You are my slut now, dont forget that." Jolie smiled and said "Okay." I went into the hotel just before her. Went into my room and got my jacket and pants off, just before I heard her knock. She was still in her ski outfit. I took her jacket and pants off too. There she was, in her skin tight ski underwear. My cock grew in my pants. I grabbed her, pushed her towards the bed and made her bend over. She looked back at me while I peeled the bottom of her. Her ass plopped out. She stood up again and I removed her top. And her bra. Then her panties. She stood in the middle my room. Just seeing her made me hard. I threw her on the bed, got rid of my cloths as well and got over her. Kissing her. Then I got an idea. It had snowed the day before and there was still some on the balcony of my room. I grabbed some snow and went back in. I kissed her again and pushed some snow into her. It melted quickly but did it job. She moaned in excitement. I got over her and pushed her down. Forced her hands down and kissed her neck. I put my dick against her pussy, she nodded and said "do it to me... fuck me.."
I waited. She added:"Fuck me really, really hard. As hard as you can..." I rammed it in. She screamed, of lust or pain, I couldnt tell. But I fucked her. Harder and harder. She moaned louder and louder. Her first orgasm came soon, but I kept fucking. "yeaah yeahh keep going, keep going..." I did. I kept ramming my full 7 inches into her wet, tight hole. I came in her. Kept going, until her felt her pussy contract for the second time. I looked at the time.

Mike could come down any moment now. I helped her stand up and we went into the shower together. When I was applying soap to both of us, she pressed her ass against me. I covered my dick in soap, then spread her cheeks and put my tip against her asshole. She said "I never had an..aaaal", mid-sentence I pushed myself into her. I didnt go all the way - I couldnt ruin her ass like Angie's - but I fucked her with about half of it. She was in pain at first, but then seemed to enjoy it more and more, until after about 5 min she said "I just came..." I pulled out and force her to suck me off. I came in her mouth. We finished the shower. We got dress and she looked at her phone. Jolie: "Oh shit Mike will be here in 5-10 min.. I gotta go!" I slapped her ass and said "Thanks for making my skiing vacation so very... unique." She smiled, hugged me and said "We'll stay in touch yes?"
I nodded and she went to her room.

And thats the end of it. Jolie and I stayed in touch for a while, even sending nudes back and forth, after a few months she either lost interest or Mike somehow made her stop again. Since I started this story I tried to get in touch again, but no answer so far and I dont expect that to change.

If you liked it, please leave a like. That will encourage me to write more :)

So, I have a confession. More of an admission I guess.

I'm not homosexual, maybe I'm bisexual. It's hard to tell, because I've never been with a man. I've always loved women, and I'll never stop wanting them. But lately, I've been thinking about experimenting with being a "bottom".

I guess I should start from the beginning here. The last girl I was with, I guess it was a year or so ago, was the love of my life. I had finally found the girl I wanted to marry, to be with until one of us died. I was happy, and she was EXTREMELY adventurous sexually. Our first night together before we were a couple involved a threesome with her friend. It was actually initiated by her friend actually. That's another tale though.

SO, after we started really dating, things clicked quick, and we fell in love. Love isn't something that I throw around without meaning, she's actually the first of any of the girls I was with that I truly felt it for.

Sex was fantastic. We fucked like rabbits, we fucked in public, in my car, just, wherever, whenever. I STILL to this day dream about the sex. Well, while she would be blowing me, she would always massage around with her other hand, and one day, she went low and started pushing her finger against my asshole.

I never really got into the idea of having my ass fondled, but she was the kind of girl who would convince me to jump off of a cliff. I mean, this girl was heavenly, with a mix of the devil. Natural beauty, un-dyed Raven hair, tits that were out of this world, hell I doubt I'll ever do better.

Anyway, so she starts working around it, and I'm not so much in a panic, but just wondering what I should do. Damn if she didn't figure it out for me, a quick deep throat made me release whatever pucker I had as I felt the ecstasy of her pleasuring, and she worked her finger right in.

She looked at me, and just held her finger in as she stroked my cock with her other hand, and smiled. I smiled too, because, I loved her, in my head I was worried that if I enjoyed it, she might think I was weird.

Well, more and more times during sex, she would work her finger in during a blow job right to the point where she started working her finger in and out. I didn't stop her, because she enjoyed it, and honestly I did too now. It was an extra pleasuring to my already fantastic fucking.

I decided to pay her back with some ass play of my own one day, and I turned her on her belly as I massaged her, working down along the hump of her bottom, spreading her cheeks and working my tongue in. She moaned in joy as I tongued her ass and fingered her clit at the same time. I had never eaten a girl's ass before, but if there was a girl to try it on, it was her. I had fun, she was very clean, as am I, so I wasn't worried about anything "gross". Who am I kidding, I freaked out at first, but in the moment, you just go all in. You know it.

Well, the next night, she decided to PAY me back for her pleasure. She told me to lay on my back, because she wanted to give me a massage. I told her it wasn't a big deal, because massages didnt do it for me. They still really dont. I don't find them too erotic unless I get a bj at the end. Which I never did haha.

She playfully tells me to just do it, so I abide. She starts massaging me, and after a few moments, I realize she started working a lotion around my bottom. Now, I've been told that if I posted a picture of my ass, and hid the fact that I was a dude, I could have men jerking off to it. I've often considered doing it as a joke. Then revealing that the ass belonged to good ol' me. Anyway, back to the story..

She starts rubbing lotion on me, and beckons for me to get up on my knees and elbows. She starts to use the lotion to stroke my dick and balls, and it feels fucking fantastic. I'm wondering to myself, "My god, how can it get any more awesome??!!" When all of a sudden, I feel a warm moistness start to tickle around my cheeks. I tensed up when I felt her breath roll over my ass, a little warm air against my bottom.

Suddenly, she begins licking and rolling her lips around my ass hole as she strokes. I tried my best to not cum, but it was probably the best feeling I've ever had in my entire life. I came BUCKETS. I'm pretty sure I applauded her.

So, some time passes, and one day after lunch on a weekend, she tells me she wants to start using toys. Again, I've never used toys. Never really figured much for them, as I have the perfect toy for a girl right between the legs.

I tell her to get whatever she wants, and we'll try them out. So, a few days later a package from Amazon shows up at our door (we lived together for a bit in a nice rental house) and low and behold, she ordered a vibrating dildo.

I joked with her and said I was sad that she didn't think my dick was up to par anymore and she laughed and said that they were the same size, she just wanted to try a few things. So the night the dildo came, I was eager to see what she had in mind.

She asked me if I'd fuck her in her ass. I'd never had anal sex with a girl before. Don't get me wrong, I tried. My ex some time before her flew off the bed in pain because I was too big. And since then, its never really been anything I thought of doing. The vagina and mouth work just as well.

I said hell yeah, and after careful careful careful amounts of effort, we got it in, and the fuck began. At first it was slow, incredibly slow. Almost to the point where I was just wanting to take it out and fuck her normal. But, as she always did, she surprised me. She started fucking speeding up to the point where it was like I was railing away at her like normal. I still was careful, I'd read too many horror stories.

In all this, I'd forgotten about the dildo. The purple, ugly, veiny didlo. The damn thing sat next to her as I fucked her ass sideways.

Now, I've watched a lot of pornos. And they've been the best education a man could ever need. I grabbed the damn thing, I never held one before, so it was like holding another man's penis. Odd. I decided I was going to double penetrate my girlfriend. I slowed down enough to work it in, and with the satisfactory moan from her, I did my best to maintain a rhythm. Eventually, I handed the rains of ol' Veiny to her and it was epic. She came a lot, I came a lot, and it was a fantastic night.

A few nights later, because I was out of town, I came home to her in a sexy little number and the ol Veiny on the bed. I figured we'd be repeating the night we had earlier in the week, and I was excited. The way she could work a dick, damn I hate the guy who she's with now...

So, we set about it, and she gets the lube out and starts applying it all over the dildo. I kind of had an idea what she was up to. I'm not a moron, and I'm horny like 99% of the time. The other percent I'm sleeping. She asks if she can use it on me.

I stared at her for a while wondering if there was a wrong answer here. I didn't know if it'd be like Indiana Jones and The Last Crusade, where I had to "Choose Wisely", or not. I decided, since she and I had been having wild nights, what the hell. We only live once.

Well, haha, it didn't work out. I did not have the anal space for anything like that, and honestly, I was terrified. I could tell she was disappointed, but not completely downtrodden about it. She told me that we'd have to work up to it. I agreed, if only to appease her.

So over the next couple of months, she would use two fingers instead of one, increasing slowly to three, to the point where it almost hurt when she was working her hand in and out.

Well, things didn't work out between us, and we ended up breaking up before ol' Veiny ended up anywhere near my ass. This is where I'm at now, and I can't figure out what's going on in my head.

I've had thoughts about having a dick jammed into my ass, and it subsequently railing it. I mean, not just any dick, a fit, young fellow like myself. Not a beary old dude. I dunno, there's just something about it that turns me on. I dunno if its because I still am drawn back to the passion with my ex, and kind of "finishing" what we set out to do, or what. I mean if that was the case, I'd just stick a dildo up there and call it a day. I think there's more to it than that.

I have what some may say is a sexy penis. Its not ugly or funny looking, its just exactly what its supposed to be. And I think thats the kind of penis I'd hope for haha. I see some of them in porn, and its kind of a turn off. So, I know its not the penis that draws me.

I've thought, maybe just a girl with a strap on? But I dunno, I feel like if I were to go that far, why not have it be a real, pulsing, throbbing cock?

These are questions I ask myself all the time. I know I love women, but maybe I'm not opposed to the idea of an attractive man. Only sexually though. I couldn't have a "relationship", per se. I mean, don't get me wrong, I'm a supporter of equal rights, politically, sexually, you name it. I'm just not gay in that way. If at all. I think its a sort of bicurious attraction that I'll never fullfill. I dunno. I just had to get it out I suppose. I don't really talk to anyone about my sexual habits, so I figure a sex message board might be the place to do it.

It was a Friday evening in late March 2019. My wife was halfway through her two-week overseas trip to visit her brother, and I had the house to myself (except for my cat). Earlier that week I’d texted Jamie to see if she was up for a visit to one of our local XXX theaters, a possibility we’d tossed back and forth since earlier in the year. She and I met the previous October, when a buddy of mine had arranged a gang bang as part of our group’s ongoing activities. Using Craigslist personals, our cadre of six to eight guys, aged 50-plus, had fucked close to a dozen women over the previous year. With that platform’s demise, activity was down considerably, but we’d had one great last party, with Jamie as the target. She’s in her mid-30s, a petite 5’1” and just slightly more than 120 pounds, a natural brunette with dyed-blonde streaks, a shaved pussy, and 34B tits. On that October 2018 Sunday afternoon, five of us guys (ranging in age from 53 to 67) worked her over for the better part of three hours. Every hole was violated multiple times, she had semen leaking out of both lower orifices (not to mention the multiple shots she’d taken down her throat), and her orgasms had easily surpassed the two-dozen mark. Driving her home later that day from the hotel room where we’d done our dirty work, Jamie insisted she’d had the time of her life.

Five months later, I contacted her to ask if she wanted to accept the offer I’d made on that drive home. Jamie returned my text midday Thursday, and I agreed to pick her up the following evening for a night of as much semi-public debauchery as she could handle. It turned out she’d just been released from jail that day, having served five days in the county lockup for failing to appear at a DUI hearing. Subsequently bailed out by a friend, she announced how horny she felt, clearly ready for some action.

She popped into my car wearing a black mesh see-through top (no bra), covered by a light zip-up jacket, plus a black micro-mini skirt (barely covering her ass) and ankle boots with four-inch heels. I asked what she was wearing underneath the skirt, and in reply she grabbed my hand and shoved it between her thighs. “Black crotchless panties. You like them?” she asked. Her pussy was silky smooth and already wet.

We drove over to Circus Cinemas, the XXX movie house in North Denver. The downstairs area is an adult store, featuring tons of videos for sale plus every possible type of sex toy you can imagine. Upstairs there are three theaters, each showing hardcore fuck films. One is devoted exclusively to gay porn, while the other two show a constantly rotating mix of professionally shot hetero porn drawn from studios like Brazzers, Vixen Video, etc. A few years ago, the owners had installed new fold-down stadium-type seats with armrests in between each. The theaters have seven or eight rows of five seats each, but the place rarely has more than 12-18 patrons at any one time.

I paid our $12 entry fee and we headed up the stairs. This place has CCTV with monitors in each theater, so it’s possible for customers to see who’s coming in and whether they’re heading for one of the movie theaters. Women don’t come here often, so the appearance of a female always draws considerable attention. Couples seem to fit into one of three stereotypical roles. Most are there for stimulation, so they come in, watch the screen for 20 or 30 minutes (some sit stoically while others might engage in some light petting), and then split, presumably to return home to fuck while the juices are still flowing. A smaller number are there to show off, gladly allowing those around them to watch-and-jerk while they engage in oral sex. We usually see the girl go down on the guy, suck him dry after a short spell, and then they leave.
The third group, by far the rarest, is where the woman is there to engage with random customers. This almost always involves her performing blow jobs on assorted guys, while her companion either (a) simply watches, (b) finger-fucks her at the same time, (c) either goes first or patiently awaits his turn, or (d) joins in. In all the times I’ve gone to CC, I’ve never seen any full-on intercourse – well, except for that one time a truck-driver type fucked a cross-dresser in his ass.

Jamie was clearly ready for us to be part of that third group. We slipped into Theater One, where she promptly led me down to the front row. Most of the action takes place in the darkened recesses of the back row, but it’s a cramped space. Jamie clearly preferred the front, where there were no obstacles for anyone to approach her. It was 7:30 on a Friday, but the place was pretty empty. I counted five guys in both theaters, and none of them seemed ready to hit on Jamie. She slipped her hand into my sweats –I’d worn sweatpants commando-style, anticipating the action to follow – while I reached over and started to play with her pussy. After about 15 minutes of this, and with no one coming forward she said, “Let’s get out of here and head over to Pleasures.” On our way out, she talked me into buying her a pint-sized vibrator from the bargain bin, which would come into play much later that evening.

West Colfax in Denver is an old Jewish neighborhood that is now mostly Hispanic. A fixture at King & Colfax is the old Act I & Act II porn house, which was bought out a few years ago by the folks who operate multiple Pleasures adult stores around town. They remodeled the place, which mostly involved splitting the two big theaters into five mini-ones, and thankfully solved the problem of the place always smelling like piss. It’s a pricier entry fee ($24 for a couple), and they’re adamant about two things, both of which were told to us several times while I waited for the cashier to hand over my change. No unaccompanied women – ever – and couples are required to stay together the whole time.

We walked through the entry door into a dark corridor lined with viewing booths. Another aspect of this place is the melding of an old-time porn theater with modern booths, each with its own video screen and hundreds of XXX movie options. Your ticket price includes unlimited viewing over a six-hour period, although I’ve never seen anyone’s ticket checked to see if they’re overstayed their welcome. There must be 40-50 booths in all; some have doors that lock on the inside, but most are fairly open. The hallways wind around in a way that you almost wish you’d brought some breadcrumbs to scatter so you can find your way out again. This place was far better attended, and Jamie certainly attracted a lot of attention as we worked our way toward the east side of the building and its multiple mini-theaters.

Each theater shows a different porn genre, and it’s marked on the doors so you know what to expect. Only one runs pure hetero porn, though, and that’s where we were headed. It’s the theater farthest from the entrance, with two rows of five padded theater seats WELL PAST their sell-by dates, plus fairly spacious aisles all around the block of seats. Jamie again led me to the front row, but this time we had plenty of company. The first guy, around Jamie’s age, wasted no time in unzipping his jeans and pulling out his semi-hard dick. She tugged on his trouser leg to urge him closer and immediately sucked him all the way into her mouth. Then she wrapped the fingers of her right hand around the base of his shaft while working her lips around the cock-head, meanwhile reaching over to me with her left hand and grabbing my wrist. She pushed my hand in between her spread-apart thighs, and I responded by shoving two fingers into her pussy and pressing my thumb against her clit.

This first guy lasted maybe three minutes and pulled out just as he was coming. Some of his semen landed on her outstretched tongue, but most got deposited on her chin. Before she had a chance to wipe it away, however, a much older guy (mid-50s?) jumped in front of her with his pants already down around his ankles. She went to work on him immediately. Meanwhile, I climbed down off my seat and knelt as close to her front as possible. Once she realized what I had in mind, she twisted toward me while pushing her companion over to the other side. This gave me much clearer access to her pussy, and I took full advantage. I did everything to her that she liked, with two fingers deep and up against her g-spot, my tongue flicking her clit and occasionally sucking on it hard between my lips, and pulling out my fingers to replace it with a rigid tongue. She loves to have her asshole worked as well, but with the narrow confines of the seating and the fact she was sucking off a guy who partially blocked my full access to her crotch, that was one maneuver that would need to wait until later.

Old Guy neatly shot his wad down her throat and got replaced right away by some hefty Hispanic dude. I kept eating and fingering her pussy, and she rode up against my face through three or four orgasms plus a total of four blow jobs to completion. My knees were getting sore, so I stood up just as Guy No. 4 (a chubby white guy in his 20s) blasted her face. At that Jamie was ready for a break, so I helped her up and scraped most of the jizz off her chin before feeding it to her. The crowd of guys, which had grown to about 15 from the time we’d started, let out a collective “Ooh.” She called out to the group, “Don’t go too far, boys. I’ll be back shortly.”

We found our way through the maze to one of the bathrooms, and I locked the door behind us as she sat down to take a pee. “Did you bring any condoms?” she asked. I admitted to be holding half a dozen, so she smiled and said, “Oh, good. Let’s go back and see who wants to fuck.” As we walked into the mini-theater to return to our seats, Jamie stopped short and confronted the same old guy who’d been her second oral customer. “You’re still here,” she stated rather than asked. “You got enough left to give me a good fuck?” He appeared speechless and could only nod, so she grabbed hold of his shirtfront and half-dragged him behind her as she made her way to the front row again. “Give him a rubber,” she instructed me, so I did and then went to lean against the side wall to watch what came next.

Jamie reversed herself and knelt on the sagging theater seat, halfway leaning over the back while spreading her legs. Old Guy dropped his drawers to display a reasonably erect dick, tore open the condom wrapper and expertly slipped it on. He leaned up against Jamie, trying to find the proper height to allow him entry. Meanwhile she reached down between her legs and helped guide him into her pussy. There was a bit of confusion and halfhearted thrusts as they tried to work out between them who was going to do what. But they eventually fell into a satisfactory rhythm, and Old Guy gave her everything he had. The room was quiet except for the XXX video playing up on the big screen, so it was possible to hear clearly the guys grunts as he thrust forward, the slap of his thighs on her ass, and the moans coming from her mouth as she rubbed her clit while getting fucked.

At this point the room was pretty full of guys. Most of them had their dicks out and were stroking them. Off in one corner I noticed, for the first time, two fairly hefty cross-dressers who were clearly T-gurls, complete with breasts on display by their low-cut outfits. The smaller one was on his knees, sucking some skinny guy’s cock. Meanwhile the larger one – at least 6-4, 275 – pushed away a couple of guys who were standing in the row behind Jamie. I later learned s/he went by the name of Brittany, since as we were leaving an hour or so later, Jamie made a point of collecting a phone number. Anyway, Brittany stood right in front of Jamie as she was getting fucked, waited a beat or two to size up the situation, and then moved those feminine garments aside to reveal a massively thick cock. Without saying a word or waiting for Jamie’s reaction, s/he pulled Jamie’s head forward with one hand while guiding that dick between her lips with the other. The sight of her choking on that monster may have been too much for Old Guy, because he quickly finished up inside her and withdrew.

Jamie forced her way off that cock and asked Brittany to fuck her. S/he grunted by way of reply and went to the front of the room. I offered up a condom as s/he passed by, only to be told in a high, lispy voice, “No thanks, I’ve got my own.” Brittany ripped open a Magnum, worked the latex over the massive cock-head and down the impressively thick shaft, and took Jamie fairly brutally. S/he grabbed Jamie’s buttocks and lifted her up off into the air, which was the only way Brittany could achieve full penetration without kneeling on the floor; that’s how much of a height difference there was between them. This repositioning forced Jamie’s head down to the bottom of the seat, her face plastered against the faux-velvet-covered seat back. Brittany pounded her mercilessly for at least 40 or 50 strokes before letting out a most unladylike bellow and freezing in place while “her” cock pulsed inside Jamie’s pussy. After withdrawing, Brittany spun Jamie around and stuck that jizz-covered dick into her mouth. Jamie calmly licked it clean and then tilted her head back so she could drain the cum from the used condom she’d grabbed out of Brittany’s hand and suspended up above her face. Those still assembled (literally) gave her a standing ovation.

As all good actors know when it’s time to leave the stage, Jamie decided the conclusion of her encounter with Brittany was the perfect exit line. She stood up, somewhat shakily it seemed, pointed to the jacket she’d shed so that I knew to grab it, and then took my hand as we made our way out of the theater. Knowing I hadn’t gotten much of Jamie’s attention so far, although I’d enjoyed the show immensely and was proud to have used my oral skills to make her cum multiple times, as we headed toward my car she said, “Let’s go back to your place and try out some of those toys you told me about. I can’t wait to run my new vibrator over my clit, and my ass needs some serious Zac-attention.” But the rest of the evening’s activities will have to wait for another time to be told.