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13
Anonymous
@confessions
21 Aug 2014 10:14AM
• 10,363 views • 0 attachments
[ − ] thread [ 9 replies ]

I hate traveling for work. What I do can be done remotely. I'm the guy relaxing at the coffee shop, or the library, sitting in the mall, anywhere I have a decent wifi connection and I'm good. On rare occasions I have to travel onsite and it sucks. This particular time was a favor for a friend. He had too much on his plate to do the job so it fell to me. Kiss the wife, hug the kids, off I go to San Diego.

The whole flight I kept starring at the letterhead on the proposal. I could swear I knew the logo, knew the name of the firm, but couldn't place it. Even when I made it to SD I couldn't quite figure out how I knew that firm. Hotel didn't do early checkin, no big deal it's a roller an a backpack I can manage. I debated about renting a car an then just hailed a cab. The firm was massive, huge lobby, hot receptionist. She took my name and told me it'd be a moment.

It wasn't until I heard the click of the heels, the gasp, and the soft voice that it clicked and I knew why the name was familiar. Standing behind me was my ex from high school. Yay awkward professional environment. She found out that morning that I'd be the one handling the job. Her boss assigned her as my babysitter while I was here. Jane didn't think it was funny, her boss probably did. Jane offered a tour of the place. I asked where I could leave my bags and the receptionist stashed them for me. I kept pace so I wouldn't stare at Jane's ass. She'd grown from the high school girl into a beautiful woman. I noticed the ring, lucky guy. She rattled off about this office or that person and I just nodded and kept going. I was here to fix the system, everything else was a distraction.

After the tour I offered to buy Jane lunch. I admitted I'd taken a cab and that I hadn't checked in yet. Just to make it overly awkward I threw in "not a date" and the smile on her face said I'd hit my mark. I was fine with taking a cab but she offered to drive. We picked up the bags and headed to some Thai place. Lunch was great. Conversation was all business until that ran out. Then things went personal. I was married, I had kids. She was married, had a little girl. We stayed away from the "since high school" cliche. I think both of us wanted to avoid talking about that part. Eventually I picked up the check. Again I offered to get a cab so as not to inconvenience her. She insisted on dropping me off at the hotel.

It was in the hotel parking lot where I sensed something was wrong. Instead of just dropping me off she parked on the side. She seemed distracted and suddenly started sobbing. She'd caught her husband Brad cheating 2 weeks ago. They were not separated. Her daughter was up with her parents for the summer and she really didn't want to go home to an empty house. I was the shoulder to cry on and I let her sob it out. I offered dinner plans and asked if she wanted to share the room. Room was already booked. She smiled and asked if I'd rather stay at her house. I started to talk about the cancellation policy and she laughed. The firm did a lot of business with this hotel, she could fix it with a single call. Hearing her laugh made me feel better. I hadn't realized we were holding hands, but I did notice her hand on my thigh. She rubbed a little bit and smiled. I didn't fight it and pretty soon my pants were unzipped.

She had her phone in one hand and my cock in her other hand. I could hear the lady's standard hotel greeting. Jane rattled off her friend's name and the lady said it'd be a moment. Jane smiled and started sucking. When her friend came on the line she popped off and started jerking me hard. She told her friend she needed to cancel the room. When the friend started talking she popped back on. 20 minutes of off and on and me having to be as quiet as possible. Once Jane hung up she worked her magic. She knew how close I was, and she didn't care. It felt amazing to drain my balls in her mouth. She stayed on a few moments longer and sucked me dry, swallowing every last drop. I tried not to laugh when she said "hope you wife doesn't mind I borrowed you".

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12
Anonymous
@confessions
19 Sep 2015 8:30AM
• 3,393 views • 1 attachment
[ − ] thread [ 18 replies ]

So, last month I went to a sex party at a club...there I was enjoying my evening, a little drunk, and a little high...while having a feel around the darkroom, I find my hands on this smoking hot ass of a girl who is busy sucking off some other guy. When presented with a beautiful round ass and smooth pussy, no man would walk away. So, after the other guy is done and I've had my face and cock in her pussy for about 10 mins she stands up. It's my fucking sister! We just both looked, not sure what to do or say. I didn't see her again until at the end of the night I was on my own, and her friends had gone, so she asked me if I wanted to share a cab home. Needless to say we went back to my place for another drink and ended up fucking like animals. She's only a year younger than me, and keeps sending me dirty texts... I want to keep doing it, but know I probably shouldn't.

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2
Anonymous
@random
12 Jul 2016 3:58PM
• 867 views • 1 attachment
[ − ] thread [ 2 replies ]

Was working in New York City for the past week,so today I finished early to get ready to go home bit wanted to go soak up some rays first. I got a cab out to the Rockaways and set up for a relaxing days sun. Had been sitting there about an hour not really minding what was around me when an older man set up just beside me, he was in his 50's dark skinned and very fit looking. We sat for awhile and I was just watching him, every time a hot guy would walk by he would touch his cook in his swim shorts.
This made me hard as fuck cause I could see his bulge. I got up the courage to say hi and in seconds we were chatting away. Then he saw my bulge and asked if I was looking at the hot girls on the beach and I told him I was looking at the same thing he was. Big smile from him and I could see him growing.
Then he asked if I wanted to go back to his place for a cold drink and of course I said yes, he lived a good bit from the beach but while he drove I would drop my hand in his crotch to tease him and it was working by the time we got in the door of his apartment he was hard and it was massive. I dropped down and tried to take it all in my mouth but I could only get the head in, so I stroked it and sucked the head like a lollipop for an hour he was so hard it was awesome. He asked if I wanted him to fuck me and why not I thought, he fucked like a twenty year old and it was heaven, then just as he was about to cum he pulled out and covered my face in his hot sticky cum. Then he slowly sucked my cock that was rock hard . He just got up walked over to his sofa and bent over the arm pulled apart his cheeks and I dove in, I was so turned on by now I only fucked his ass for about a minute before I felt the surge of cum in my balls I pulled out and shot my load all up his back and covered his ass which I then licked clean,
,I can't wait to come back to New York, and sit on the beach again ,as he drove me back to the hotel he said next time he will arrange a couple of friends for a get together. Can't wait!!!

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Anonymous
@confessions
22 Nov 2011 12:45AM
• 807 views • 0 attachments
[ − ] thread [ 6 replies ]

I love watching my wife fuck other guys. Just about all of my friends have fucked her plus hitch hikers,delivery guys, room service waiters, a hotel masseuse, a few guys on a nude beach 2 of them in the dunes with nobody around 1 right on the beach in full view, a cab driver, 6 guys in a bar after closing, her boss, her sisters husband. She was a 18th birthday gift for a kid who lives a few houses down from us and a 76th birthday gift for a father of a friend. Befor any of you pics or it didn't happen jerks speak up we don't take pics or vids of any of it. Some people on the beach took pics and vids they might have made to the web but we have never seen them and the guys at the bar wanted to but we wouldn't let them. Not all sluts want to be on the web.

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7
Anonymous
@confessions
04 Jun 2014 8:05PM
• 14,160 views • 4 attachments
[ − ] thread [ 12 replies ]

I'm nearly 60 and have enjoyed 30 years of paid sex with some really memorable occasions. Unlike many other guys who have satisfying sex lives with partners or girlfriends I have had to pay, but I have used the opportunity to have sex with attractive young women that I would never have been able to enjoy any other way. I'm always after the elusive girlfriend experience, however but treat girls well and have often been very pleased with the outcome.

A bit of history: Back in 2010 I used the Adultwork website to meet up with a beautiful 19yo photographic model model (we'll call her Clare) who also liked to offer extras. After a very successful sexual encounter I told her I enjoyed gangbangs. "What's a gangbang?" she asked! Well I didn't just tell her, I felt obliged to educate her properly and organised one with myself and 3 other middle aged guys. She and we loved it and she held several with other organisers before at Christmas 2011 I suggested another new experience, a visit to a well known naturist/swinging club. Let's call it Oreos.

All organised, several guys and her met at a pub before going the club. At reception, however she was turned away. We hadn't realised they had a 21yo age limit and she was 4 days short of her birthday. Fortunately one of the guys had a hotel room so we were still able to party but this was always the special event that didn't happen.

Soon after that Clare started a relationship and stopped working. She became pregnant and had three children. She left a lot of punters bereft, we wished her well but she had been one of the most enthusiastic and lovely amateur hookers, with a genuine fondness for older men and a strong exhibitionist streak and sense of fun.

I could never get over the missed event however and kept trying to arrange it with other girls. In the end I advertised a reverse booking on Adultwork and my very cheap offer of £100 for 'at least two hours' at the club was accepted by a girl calling herself Lush Companion. She was delightful, half Philipino, petite and sweet. We stayed the whole evening and I had a great time. We treated two guys to joining us in a private room although they only got to watch us and be wanked off by her.

Earlier this year, I heard rumours that Clare was working again and established email contact. In a racy chat session she let on that she felt occasionally stifled by motherhood and craved the attention she used to command from guys. She also wanted to prove she was as tight and passionate as before she delivered her babies vaginally. She was proud that her figure was almost as slim and firm as before.

We arranged to do the Oreos visit nearly five years after the first time. She would travel from home in Birmingham to Bristol, I would pay her travel expenses, plus £60/hour for two hours and would try and arrange a couple of other guys to increase her income and make up more of a party.

I advertised on Craiglist for single guys to "share an 25yo slim amateur hooker at Oreos" and when I had a disappointing response, advertised for couples as well. I did have about 2 guys and 2 couples expressing an intention to attend and participate. As it turned out nobody from Craigslist or any of my usual gangbang circulation list turned up (Losers) but we had a ball anyway.

When Clare's train arrived I was delighted to discover she was just as pretty and slim as I remembered and just as friendly and up for it. She looked stunning in the nude at Oreo's and I enjoyed a shower with her as she experienced some initial embarrassment.

Clare was only shy for about ten minutes and then realised that there were worse fates than being fancied by 20-30 blokes. She really entered into the swinging spirit. We fooled around in the Jacuzzi, were joined by a black couple who were very naughty with each other underwater. The woman, Kate, said she wanted to lick Clare out so we went to the largest of the private rooms. I could tell that Clare was really getting off on the very polite but obvious attention from guy in particular one and feeling magnanimous to both Clare and the guy said Puss could do whatever she wanted and she asked the very 'buff' and extremely nice guy, John, if he wanted to join us to 'help use up a bottle of baby oil'.

In the private room I french kissed Clare and slathered her slim torso and pussy with oil while Clare wanked John. She then sucked him while the Kate licked Clare out and fingered Clare's pale pink pussy with her brown fingers and crimson nails whilst declaring that "Oh my god you have most gorgeous pussy (True) and you taste so good". While she did that her partner fucked her in doggy with his stereotypically large cock.

Then I said it was Ok, so John found himself fucking Clare but forbidden to cum. He and I took her in turns and in several position before he came on her smooth belly. As the client, I reckoned I would finish the session by coming inside her. OMG that was lovely. Winston was fiddling with her anus and my balls which I quite enjoyed but Clare didn't appreciate!

Winston was pissed because Clare wouldn't let him fuck her "You'd split me open" she said, which seemed unlikely seeing as she had delivered several babies, but she was still very tight and I gather she had had a bad experience with a BBC in the past. Absolutely her call, after all, I was the only one paying!

After the joint session in the private room John had to leave. He had a huge grin and still couldn't believe his luck having had Clare choose him and me telling him he couldn't come until I said so!

With only 45 minutes until we had to catch the train, I had a second wind and having asked Clare just for a cuddle, we had a very sweet spoons and cowgirl quickie session in a clean private room, by ourselves (I'm afraid we left the other one with soggy towels and pools of oil and worse. Disgraceful!).

Well, after two and half hours in total at the club we ran out laughing into the street and hailed a taxi, getting her to the station just 5 minutes before her train. I don't know how many times she came over the evening. I managed more than I thought I was capable of and the subsequent Viagra headache was just mild enough for me to bask in the afterglow.

I won't forget this amazing experience for a long time. It hugely exceeded already high expectations, mostly because of a wonderful girl and a very good vibe at the club.

It cost me £140 for her (all I could afford), £15 entrance (special offer for couples on Tuesday), £30 in cabs, £40 for her train fare. This is twice as much as I've ever spent on a punt. Would have got 4 half hour sessions with my hometown regular - but what an experience!

She and I have exchanged texts and emails over the subsequent 24 hours. It is abundantly clear that she really enjoyed it. I'm so glad.

Details have been changed to protect the guilty but this actually happened last night 3rd June. I know - I was there !!!!!!!!!!!!!!!!!!!!!!

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Anonymous
@confessions
21 Feb 2026 4:12PM
• 148 views • 0 attachments
[ − ] thread [ 4 replies ]

I confess I can’t stop thinking about my ultimate fantasy of being used by a group of a specific type of man. I’ve always been attracted to truckers and other blue collar types, I loved the way rowdy older guys outside of bars would catcall and look at my ass as I walked by, before I was even old enough to understand what I was feeling. I love being lusted after by crass, perverted older men with no shame. It makes my pussy drip with anticipation.Ā 
My ultimate fantasy is to get picked up by an older man and have him blindfold me and take me to a spot where his friends are waiting, and they’re all making vulgar comments about how much they want to use my body, stripping me naked and roughly exploring my body. I’m white and 5’1, a natural redhead and I’ve always been thick and curvy. I have a soft chubby pussy that stays waxed and smooth. My body looks so good in ropes, so my fantasy involves being tied up and placed in a swing or another apparatus that leaves me helpless with my legs spread open. I want to be taken advantage of, fucked in all my holes and told how good my juicy pussy feels while being used like a toy. It turns me on so much to be the center of a shared experience for a group of buddies with big thick cocks and rough hands. Even better if some of them are BBC. I’ve always desired being taken advantage of and used for black men’s pleasure.Ā 
Maybe it’s you and your boss at the construction site, spit roasting me in his office, or maybe you and your trucker friends toss me in the back of one of your cabs and take me to a remote field where you take turns filling me. Maybe you work on cars all day and then you & your coworkers decide to have me as an after-work treat in the back of the shop.Ā 
When you’re done using me like a toy, you drop me off back home to my husband, filled with other men’s juices and never telling a soul. You an your buddies deserve a nice release every now and then.

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Anonymous
@random
16 Nov 2015 7:05PM
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So I went for a few beers after work in a local dive bar, when I got in it was a good crowd of the usual suspects and a cougar that was new, I got the empty seat next to her at the bar and after a few minutes we got into a conversation about general shit, I bought her a few drinks and then she got all flirty. Two hours into kit she said she had to go so she went out to call a cab, when she came back in she asked if I wanted to go into the parking lot to say goodnight cause the cab would be 15 minutes. Out we go and she drops my pants to the ground and starts blowing me and it was good. I came in her mouth about ten seconds before the cab pulled in and she just piped up and jumped in the back .I pulled up my pants and the fucking bitch had stolen my wallet. Most expensive blow job ever!!!

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Anonymous
@confessions
30 Dec 2012 9:19AM
• 2,215 views • 0 attachments
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I think i'll start off by describing myself, i'm a young guy, about 5'8'', short brown hair and brown eyes. i'm in good shape, i like to keep fit and am in the gym a good bit during the week. about a month ago now, i met a guy there named Ryan.
Ryan's a few years older than me, in his mid 20s, about a half a head taller and in very good shape. the first time i met him, i was mid-workout and he came over and asked if i needed a spotter. i said sure and we got to talking, i commented on how i liked his beard, we joked around, and finished our workouts together. i thought he was just a cool guy and that he wanted to make a new friend. it never occurred to me that he was gay, i'm straight so i wasn't on the look out for any signs that he would be attracted to me.

at the time i didn't know he was gay so when he asked me if i wanted to go to a club with him about a week after meeting him i said sure. we got a cab in that night and on the way he leaned over and asked if i'd ever tried this before, while holding out a little blue pill in his hand. as a matter of fact i had tried extacy before so when he offered me one i happily received. about 10 minutes later we were in a dark club with dance music pounding from the speakers. it was the kinda music people would associate with gay guys partying but i liked dancing to that music so i still hadn't put 2 and 2 together. it didn't take long for the extacy to kick in and boy did it hit hard. i felt amazing, i could feel the beats of the music in my skin, i couldn't stop dancing if i tried and i was talking to anyone near me. now for anyone who hasn't taken extacy before, you have to realize that it makes you want to dance, a lot, which means you sweat and have to make sure to drink a lot of water or else you'll get an unbelievable hangover the next morning. it wasn't my first time, so i knew i had to keep drinking, but that also made me need to piss pretty bad.

i didnt know where the bathroom was so i asked Ryan and he'd brought me over. he said he had to go too but when we walked in all the urinals and stalls were taken up except for one. Ryan looked at me and said "lets just go together, we're both guys so it's not a big deal right?". that made sense to me, like i piss beside guys in urinals so what does it make a difference in a stall?

i was bursting so i just agreed and rushed in. as i unzipped my pants, Ryan came in behind me and closed the door. i thought that was kinda weird so i turned around. as i did he grabbed my cock and started kissing me. i was in complete shock, i was just stuck there for a split second thinking "what should i do?!". he kept pulling my cock, and i don't know if it was the pill but it felt amazing. i started to get hard and he dropped to his knees and took it in his mouth. he took my whole cock in his mouth and i didn't even care that he was a guy at this point, i was just entirely focused on the feeling of his warm, wet tongue sliding up and down my shaft. he got it nice and wet before he started stroking it and sucking my balls, moaning while he did it. it didn't take him long doing that to make me wanna cum, so i grabbed the back of his head, and shoved my cock as far down his throat as possible. the feeling of my balls contracting as i pumped my cum down the back of his throat almost made me pass out. i collapsed back on the toilet seat as he stood up wiping his lips and said "see you outside" before leaving the stall. i pulled my pants back up and went out to dance more, because i was still high as fuck.

however, i did make sure to return the favor as a thank him on the cab drive home ;)

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Anonymous
@confessions
15 May 2012 9:53AM
• 1,748 views • 0 attachments
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I went to a popular rest stop this morning. Sitting at a picnic table near a tree was this big, black trucker eating a sandwich.

I went in to use the toilets and couldn't keep thinking about how sexy he looked. It was soooo tempting to ask if he'd fuck me. The thought just wouldn't go away.

Never, ever have I done something so bold and daring. Not only that, I knew that he could just as easily beat the shit out of me if he wasn't interested. But I threw all caution to the wind.

As soon as I came out of the toilets, I walked up to him and said, "I've always wanted to feel a big, black cock in my ass." He practically choked on his sandwich as he turned to look at me. I thought for sure he was going to cuss me out or come at me with his fists.

But to my utter surprise and delight, he replied, "And I've been thinking how good it would feel to fuck some white boy ass." And with that, he wrapped up the rest of his meal and led me to his truck.

This was the first time I'd ever been in the back of a semi cab. It was amazingly "spacious" for such a tiny space.

That man fucked my ass HARD! He came inside me and spilled so much seed it dribbled down my legs.

I've never done anything so spontaneous in all my life. He didn't even use a condom and I regret that part. I will be checking myself for AIDS and STDs soon. But at the moment, I'm glowing from my own orgasm and I am thinking that the experience was so worth it.

He told me when he usually comes through this way. I am definitely thinking of meeting him again.

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Anonymous
@random
21 Apr 2021 5:41PM
• 653 views • 4 attachments
[ − ] thread [ 6 replies ]

I love jerking off to girls I hooked up with in college. Wish I’d been better in the early digital camera years about taking photos, but I have stories to go with what I do

I finger-fucked this girl with three fingers in the cab on the way home on my 21st.

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