The night I fingered a crackhead and why I remember it fondly. 

A used to assist a friend in throwing some epic parties 15ish years ago. One night, after a few too many, I fucked a short portly blonde. She wasn't ugly by any stretch of the imagination, but she wasn't a stunner. She sat firmly in the 6-7 range. You know? Attractive enough to fuck sober, but you worry they'd get clingy and want to be a thing. Even now, at 37, chatGPT rates me an 8.5 for conventional attractiveness, even after I told it to be harsh, so you know... I've got that goin' for me. BUT, to my shock, she pulled a switcharoo and didn't want people to know she fucked me. ME!? 

Fast forward 12 years, and we reconnect on FB. Her husband just died, I just got a divorce, and it was nice to have someone to talk to. Her condition was evident in the photos that she was a user, but we weren't "talking" like that, so it was whatever. We hung out once, and it was a buddy hang, not a fuck buddy hang. 

Months go by, and I start receiving texts. The government took her sex trophies and she was homeless. Not like this was an ongoing situation, this had all happened within the last 5 hours. She had a ride somewhere later that night, but was spending some downtime at a casino. I thought, "Well, damn...I could bring her food and toss her 50 bucks, seeing as how she's broke and probably hasn't eaten all day." I get there, and after a while we decide to head to my car to continue our very lengthy conversation. It's, like, 2:30AM.

It was here that she started to fall asleep while I rubbed her boney shoulders. No exaggeration, she is 4'11 (jail records confirm this) and at the time MAYBE 85lbs. She coils into my lap, so I slide my hand towards her hips and continue rubbing. I'm a stand up guy. A saint, really. So, I ask permission to slide into her panties and I get the okay! I'm using both hands to grip her hip bone, and I might as well have been gripping a prop skeleton. I slide my hands in and started to rub her pussy. She lets out this raspy crackhead moan... You know the one. She honestly sounded like she was on death's door, which is actually why I'm telling this story, as it occured to me today that I should Google whether or not she was still alive. This went on for about 15 minutes. 

The pros, and why I remember it fondly: No ass cheeks. Everything was easy access. No thighs to move out of the way... it was just pussy and bird legs. Her little body curled up in my lap next to my hard dick made me feel massive! 

The cons: Dehydration. She couldn't get wet and her pussy was a walking swiftly into "don't touch it" territory smell-wise. These crackheads just don't care for themselves the way they should. 

The end. 

I confess that I lost my virginity to my first cousin and I want to fuck my sister. My cousin and I would watch porn that she stole form her dad at night, after my grandmother went to bed. Before long we were trying things from the porn on each other. She always kinda chubby but not too much and she was always pretty. Her pussy, ass, and tits are very nice. For a while, we just did oral stuff, I ate her pussy and licked her asshole and She would suck my dick, lick my balls and ass, she's great at it. I watched her go to the bathroom and other kinky things like that. But I did not penetrate her for a while. My cousin lived at my grandmas so we could only have our fun when I visited.

At home I was full of sexual frustration. I had to live with my beautiful sister who won't do things like that for me. it was like torture. I stole her dirty panties a lot and once jerked off over her while she slept in her room. The closest I got was one day during spring break in High School. Both parents were at work and I was sitting in the couch, just hanging out, around noon. She and I smoked weed together and she walked into the living room and asked if i wanted to burn, I said yes and followed her to the garage. She was a robe with pajama bottoms under it and her hair flipped up into a towel, she had just showered. After smoking and getting super faded, We return to the living room, I sit where I was and she curled up into a kind of ball to leave space for me to sit on the couch. I was turned on just sitting next to her.

"You can stretch out, put your feet in my lap" I told her. She kinda smirked and said, "really?" she kinda laughed. I reassured her and she put her feet up into my lap. After a while, I put my hands on her feet and started rubbing them. She look at me funny at first, but started to enjoy it. She let me do this a while, I got a boner while rubbing her feet and I felt like it was gonna rip outta my jeans. She fell asleep. I watched her sleep for a few minutes and whispered her name to make sure she was sleeping. She was, and I ran my hands down her leg and felt her inner thigh, she was so warm and smelled so good fresh outta the shower. I was so horney and I got carried away, I pulled my cok out and touched her feet with it. This is when she woke up and jumped up at the sight of my cock. She told me to put it away, she said we were brother and sister and that thats wrong. she said she wouldn't tell anyone but i shouldn't do that, she left the room. I went into my room and jerked off violently, I was kinda furious. It was rough for the next few weeks until I went back to my grandmas.

My next visit to grandmas, after the sister incident, I told my cousin that we need to fuck. She was reluctant but finally agreed. I got hard instantly, and was read to go, she pulled her pants down and I ate her pussy for like 2 seconds, just enough to get it wet and then shoved my dick in her beautiful pussy. This was the first time I was inside a pussy and It was magnificent, I waited so long and it was better than i ever though. She told me not to cum inside her, and I said I wouldn't, I didn't mean too, but It was so good. I couldn't pull out. I cam so hard inside her. We were afraid she would get pregnant but she never did, and we where way more careful after that.

Me and my cousins stopped having sex for many years, but started again about 3 years ago. Now, I live a lone and every few weekends she will come stay and we still have fun. I want to try to talk her into making some uploads for this site, Lets see how it goes.

So sexy when a woman curls her toes when she’s masturbating. 

Need Advice pls.
Have been seeing my gf a couple of years and our sex life is healthy but her teen daughter kinda flirts with me. She sometimes comes into the bedroom when I'm changing and stares at my crotch, commenting on how many buttons I have on the fly or says "look at your sausage sticking out" when she can see the outline through my shorts.
She like having a back and shoulder massage as well as running my fingers down the back of her arms as it tickles her and gives her goosebumps. She pretty much likes gentle "tickles"/strokes anywhere on her shoulders, collar bone, back of her legs etc. So over the months theres been a few incidents. She's had on short sleeping shorts and one weekend morning we sat on sofa together, she was curled up with her bum facing towards me and I spent ages stroking the back of her legs, right up the top of her thighs and even across the bottom of her exposed bum cheeks. She liked it but never says much other than "it tickles" and she squirms and giggles. Also she doesn't wear a bra in bed, the other day I came home from work and she'd been home all day ill. When I sat with her, she put pillow on my lap and laid back on it playing on her iPad, knees bent up and I was stroking her head, tickling her arms and also just above the hip bone where its sensitive. Pretty much all round her exposed midriff, running my hands along and up her rib cage and I was literally about an inch from the base of her breasts!! My heart was pounding, I could see her breathing was increased but she just lay calmly lapping up the attention. When I ran my fingers along the waistband of her pyjama bottoms, due to her slightly curled position and being long-legged but short body and having her knees bent right up, her crotch was only about 6 inches from my fingers. I didn't know whether she was just waiting to see what happened or what. Another weekend morning we did a similar thing but she lay on one side with her face inches from my cock! Back in summer she put her hand almost right in my lap so I could tickle the back of her arm and she kept twisting it about so I could tickle all of it but the base of her thumb kept touching my cock which then got harder. Next thing I know, rather than putting her head in my lap with a cushion as normal, she just plonked her head down right on my growing erection!! I didn't know what to do or say and her mum was in the house this time so stayed quiet.
Another time she asked for a proper back massage so got her to lay on my bed, again on a weekend morning, small vest and shorts, no bra and I spent ages doing the same, running my hands over this tall slim, pretty blonde girl with a bubble butt!
One night in bed she got in to give her mum a rare cuddle (shes too old for all that really), I got in behind her and she shoved her bum right back in my lap and I know she could feel all my package! I only had thin boxers on and my cock started to grow so I twisted away slightly cos she's cheeky I thought she might call out "whats your sausage doing pressing against me" or similar cos she thinks saying things like that in front of her mum is funny. After I twisted my cock away, she moved her bum about, not sure if she was trying to find it!! Me and her mum are pretty open and they both know I'm comfortable with nudity so her mum trusts me around her, luckily.
On another occasion I'd been in the shower and was stood in the bath still drying off and her mum called up to me from downstairs so I opened the bathroom door to shout back, the step daughter was in her room and knew I'd just been in the shower and without asking or knocking on the open door just walked into the bathroom! My towel I think was just covering my cock but I don't know. We all just laughed it off. Unfortunately the hand in lap or looking at my crotch while I'm changing hasn't happened for a while.
Really don't know what to do, she's gorgeous and its a massive thrill stroking her body and being inches from her bare breasts while she lays happily on my lap. How would you guys take it from here? On one hand she prob wants something to happen but its seriously taboo, on the other, she may just enjoy the attention.

Curling everybody! Me and ex cuck all her dates and bf! Have threesomes on the regular! me ,her and my dog! She such a dirty bitch in heat lol  I really made her into the best friend one could of ever want and need!

2 in 1 confession. I saw my mom naked. She didn't know I was upstairs and she walked out of the bathroom after a shower and we ran into each other. She covered her top but not her bottom and she went right back in the bathroom.

That was the first time I saw her fully naked. I've seen her pussy before a couple years back as a teenager. One summer night she fell asleep on the couch and left the TV on. I went to get the remote and there it was fully exposed and on the edge of the couch (she was curled up facing inward and her nightgown rode up). spam-boner. I started rubbing myself and then got a little daring and started rubbing my dick against her pussy lips. I was nervous as hell and hoping the TV was loud enough to drown out my heavy breathing and low enough to not wake her up, of course, simultaneously thinking of a plan B explanation in case she wakes up. I felt myself getting close and rubbed a little faster. The taboo alone was extremely arousing. I felt my first contraction and it shot on her pussy lips. My better judgment compelled me to point my line of fire away. Grabbed some nearby tissues and cleaned up the crime scene before making like a tree.

My cousin is my best friend. She's 19, has an amazing body, and a very cute face. We hang out once a week, have lunch and shoot the shit.

She's always been very physical with me, nothing overtly sexual... just full on hugs, sitting on my lap, that type of thing.

A couple months ago she upgraded to talking with me about sex, and what she wants, as well as sending me pictures of her in skimpy clothing.

Last month she spent an entire week at my house. Most of the time she spent walking around half naked, or curled up in my bed. The last night she was here she came to my room while I was reading, took off every article of clothing, and tried to make out with me... I got up and left the room. The next day she claimed she didn't remember any of the prior night due to the copious amounts of alcohol and weed.

I want nothing more than to fuck her brains out, however, I know this would completely change the dynamics between the two of us. Personally I like having somebody that is constantly talking to me about sex, and sending me pictures, and turning me on... gives me something to think about when I fuck randoms.

Should I go for it? Fuck her brains out... and never talk to her again? Or should I continue to be turned on by her daily and fantasize about her when I fuck other chicks?

This is a communique between myself and a girl I used to fuck. My responses are in quotations.

The previous times they had slept together the intensity had escalated nicely, organically and without the tedium of words and planning. The first time he fucked her it was hurried and urgent, racing the clock before his unsuspecting roommates would return home. After barely five minutes he'd shook his head and uttered "you're too much for me" and pushed deep as he released inside her, behind latex. Several dates later as he fucked her bare, she whispered in his ear that she'd love it if he didn't pull out this time; breathlessly he confirmed the request and almost immediately came, shaking as he shot hard within her eager body. She loved the warm wetness when he pulled out, and the slick reminder of him lingering inside her as she went about her day.

But on this day there was a certain new edge to the energy between them, something menacing coming to the surface as he suddenly threw her against the bed. Then back to gentle and tender kissing. Light, grazing touches. Her heart raced, having no idea which direction all this was taking. The slight fear of him was terribly erotic and she gave herself over to it. Her manner shifted almost imperceptibly. Her entire body seemed to take on a slight posture of invitation, ready to be used, and her wide eyes flashed with willingness.

"The form that flesh takes and in its desire. To be lost in the rage and despair. It is but a knife edge, the menacing nature below the surface. The need to contain, dominate, dictate. And that tenderness reminds me of the intimate, the senses satisfied, which while I do feel, I prefer the hollow, the shell of fear, the unsuredness of ones own nature. The slope upon which we fell, I revisit daily. I would use your body again as a vassal, I would grip more firmly the control of us, and less firmly of me, for in those moments I come closest to my limit.

In cruder terms I want you as an object, a canvass for sexual mistrust and rage"

He flipped her again harshly and without warning, face-down on the bed. He straddled her just below her hips and she felt his cock pressing, searching. She arched up as much as she could and gasped as he slid his whole thick length into her. She loved how full his cock always made her feel, she felt stretched tight around it, truly penetrated. The first few thrusts were deliberate, even casual. Then he started to pick up the pace, until soon he was drilling into her. He leaned forward and wrapped a strong hand around her throat, squeezing enough to cut off her breath. Another flood of fear mixed with excitement washed over her and she tensed. The grip released and she drew in breath sharply, panting. He grabbed her right arm and pinned it behind her back, hard. She rode the discomfort of it, mentally aligned the pain of her twisted elbow and shoulder with the intense pleasure of being fucked. He grabbed her left arm and pinned it the same way. She fought panic and took in the fact of being in this helpless position for the first time. Now he kept both of her arms pinned firmly with his own body as he leveraged his weight forward and gripped her throat again. She felt pressure build behind her eyes and the sound of her pounding heart filled her ears. Release, gasp for breath. Grip, release. Gripping again, this time a fraction harder... unconsciously she pressed into his hand, craning her neck to encourage him. She was overwhelmed by her pleasure in submitting. In that moment she desired to be hurt, taken, used for his pleasure in any way he demanded.

"The body remembers well. The cock pressed inside, against the back of your throat. Spreading each orifice anew. How taut you became under my hand."

What are you going to do?" He murmured it so low she had to ask him to repeat it. Slightly confused, she replied with uncertainty "I don't know..." They had scarcely spoken a word during sex in previous sessions. With a serious face he looked her over and said very slowly "You are going to do whatever I want you to." Blood rushed to her cheeks and between her legs as she silently nodded assent. He grabbed her legs roughly and spread them wide in a swift movement. There was a controlled measure of violence in his face and she gazed into it, showing him her fear mixed with arousal. Still looking her in the eye, he reached down and slid two fingers inside her... slid out and back with three... slid out and back with four. She moaned low with pleasure, pushing against his hand as he rocked it back and forth, curling his fingers inside her. He started to push harder and she felt the hard knuckles of his hand pressing to gain entry. She gasped in audible pain, involuntarily closing her legs around his hand. He relented, easing the pressure and the pain returned to a pleasurable level. This exercise was repeated a number of times, but in the end the pain was too great when he tried to force his hand inside. So he raised it, warm and wet from her, to her face and she opened her mouth obediently, eagerly. He slid all four fingers into her mouth and she closed her eyes in enjoyment as she cleaned her taste from them.

I have a confession.
I visited my little sister at her new house because I was helping her decorate.
When she got there she was wearing this old wifebeater and jean shorts, but I couldn't take my eyes off her lovely bare feet and painted toes. She is about 4'10 and brunette with an arse and pair tits of a young woman much bigger than her...Not that I'm complaining.

We had painted 2 of the 4 walls in the guest room, when the song "Hips don't lie" by Shakira came on the radio, and she jokingly started to dance and shake her arse like Shakira. I took the opportunity to dance with her, because although she didn't know about the terrible things I wanted to do to her, we have always been close. I started out slow, running my hands down her sides, and then into her back pockets. Just feeling on that nice round arse. She had nowhere to go with my hands in the pockets, and I took a firm grip and pulled her close and brushed her hair away from her neck to kiss her there. She began to purr and she swore under her breath repeatedly (I love her potty mouth, because although she is 19 I still feel I can spank her for being naughty :P).

She just pulls away from me, looks me in the eyes for a moment, and lays on the carpet. I get down to my knees and lift her legs in order to suck on those toes and kiss her all the way up to her shorts. I slip my hands into the waistband, her stomach warm against the back of my hands, and I unbutton the shorts. I pull them hard as she allows herself to go limp, and they slide down her beautifully formed legs. I pull her Wonder Woman underwear (I remember them, because there is something about a grown women in kids pants) and chow down in Chinatown. She writhes around moaning the whole time and I hear her scratching the carpet with her nails as she tries to grab hold of something. She cums hard, and pushes my head away.

I crawl over to where she is lay curled up in the fetal position. I grab her arm and pull her back over onto her back. I didn't mean to throw her around like that but the thrill of her being so defenseless and weak excites me, so I keep going. I straddle her and put my hands around her neck. She blows me a kiss and shakes her cunt under my weight, almost like an invitation. I slip my dick in her, her tight pussy takes my breath away and I feel like I'm gonna cum almost immediately, so I just kiss her stomach and feel those perfect tits. I fuck her softly for hours while the fan stood on the chair blows through my hair. Today was a good day.

she was awakin one morning with her dad in bed with her and his hand down the front of her panties. of course she was shocked scared and frightened. he calmed her quickly and let her know who it was. she say she ask him several times what he was doing and for him to stop. says her pussy was soaked and his middle finger was burried deep as it could go inside her. she was liking it and he knew it. she had set on his lap for years in the recliner watching tv and learned she could squrim around and he would get hard under her ass. she didn't know for a while why or even what it was but she liked when it would happen. he was priming her then by doing nothing about it. he never tried to expose it to her or acknowledge it in any way. this had happened as late as two days before her mom left for ohio on business. she was two weeks from turning fifteen. she couls feel his bare hard cock against the side of her leg throbing. he told her she had one chance to say no and he would either go or stay till morning. she remembers vividly saying don't leave. with that he kissed her and she fumbled with his tounge in her mouth and kissed him back. he then mounted his self on top of her and opened her legs as far as they would go moving the leg of her panties open he lined up the head of his uncircumsized cock with her flower and showed her how to open it for him. she felt the pressure of his dick pushing against her and as he pushed harder the head went inside. she says he rotated his hips a bit and pushed further. it hurt. he would pull it back out and then go a little further the next time as he found the path she could literaly feel herself tearing inside and excepting his fat cock little by little. he had given her her legs to this point and let her move them about, then he hooked them in front of his elbows and started pumping slowly in and out to as deep as he had already been. he was just better then half way and without warning or sign he broke the established rythem and let his body sink to its fullest inside her. she tried to buck him off of course and all it done was take him in deeper. she resolved the fact he wasnt going any where and her body relaxed to except the act. he started a slow grind with his pelvic bone against her clit, she was in pain and in extacy at the same moment. he did not pump her for a good while she says. they just lay there. she says she can still close her eyes and feel her pussy contracting around his member. then comes the fetish for dirty talk he started telling her how good she was making daddy feel, she was a woman now and he was going to fuck her like one. he told her with his loins grinding against hers that if she ever told anyone at all even her best girlfriend, it would mean he would more then likely go to jail and her life would change for the worse for ever, he says you must not ever tell baby girl. she said ok daddy. then he started back out as slowly and gentel as he entered. he got half way out then went back in all the way each time getting longer then before till he was fucking her full on. she says she would moan and whimper and would say in her ear you are driving daddy wild little girl, your pussy is better then mommies, you make my cock so hard. do you like daddy fucking you? this was the ultimate, you know you are daddies little slut now don't you, and she said nothing, he gently pulled her hair for the first time, and said it a little louder and she responded with yes. he came inside her with his vas. safe cock. rolled off and let her curl up next to him and go to sleep. this went on for two years. then theyy decided it was time to stop before some body found out like mom. does this excite you or turn you off??

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.”