Most unexpected sexual encounter

GorillaHorse said:

I grew up in one state and moved to another. This girl from where I grew up was in rehab I believe in the state I moved to. I picked her up, took her to a party that was going on at a friends house, fucked her in an empty bedroom at the party, left the party and drove her back to rehab. It was bonkers. And she had the biggest tits and super skinny. Really blew my mind and probably led to me getting my first beautiful slampiece from the state I moved to.

It was a surreal moment but I remember most of it vividly.

Click to expand...

Taking advantage of a bitch in rehab... you’re a class act

CalifornianSTUD said:

I have a ton but I would say the absolute most unexpected was when I was leaving an escort job at a pretty fancy with a pretty attractive young rich guy. As I’m learning I stop by valet and a cute little Latino guy is working. I hand him my ticket and says “we both have Kias”. I smile and say “oh, nice”. He then says “most people who stay here drive very nice cars”. I say “they are over compensating”. And he says “like you mean they have small penis?” So I say “yea, something like that”. He says “so does that mean you have a big one?” I said “no, it’s not big, it’s huge”. He says “must be nice. I wish I had a big one”. I say “do you want mine?” as I slowly unzip. He pulls me into his little booth and I whip it out. . We start making out and I undo his pants and lower them enough to where his ass it out. I flip him around and spit on his hole and then go to town. He moaned ‘ay, ay, ay, ay, ay... for 45 minutes straight. When I was done he asked what room I was staying in but I told him I wasn’t staying there. He asked why I was here at 4am so I told him “I was paid by a guest to fuck them for the past 3 hours”. He then asks “you fucked him for 3 hours then came right to me?” I told him yes. He then asks how can he find me, so I gave him my number.

Sad part of the story, he was deported a week later.

Less sad part is, I flew down to Guadalajara a month later to see him. He was fine but had 8 roommates. When I stayed there he told them all to let me fuck them, so during that week I had a house of sexy little Mexican guys at my sexual service.

Click to expand...

LOL, I wonder why he was banned...

TypicalWhiteGuy said:

Taking advantage of a bitch in rehab... you’re a class act

Click to expand...

The way I see it, she took advantage of me. It is e.x.a.c.t.l.y what she wanted. She was 100% sober, and we had a great relationship. I was also very young. Like teenager bro. Chill the fuck out.

Aren't you the guy who fucked the guy that he beat up for being queer? Are you sure you want to do this?

When my wife suggested I come home for lunch on her day off, and arrived to find a nooner waiting.

The first time I played homewrecker, seeing as I didn't know he was bi lol I was crashing there bc he was married to a relative who let me stay there for summer vacation and he slyly said something about me having a fat ass while we were watching tv one day and on thing led to another

one*

sangheili90 said:

Not that long ago I was out grocery shopping and after checking out at the register I was stopped by one of the employees there when I was walking out the door. He said to me that there was an "older woman" who wanted to give me her card and that she wanted me to text her sometime. I took the card, having no idea who the woman was or what she really looked like, he described her to me and I recalled seeing someone who matched her description but I didn't actually meet her.

Anyway, I got home and decided to text her, as I didn't see what harm could come of it and it would prove to be an interesting experience. She replied relatively quickly, we texted back and forth a bit and we decide to meet up at her place later that night. I spoke to her briefly over the phone just before I got to her house, but I was pretty anxious about the whole thing.

I arrive to her door and I see a woman who is substantially older than I am, my initial impression was that she was 60+. She lived in a small town house with tons of other homes around so I didn't feel all that unsafe. She invited me in, as she was still getting ready, so I sat down on her couch as I waited. To say the least I was very shocked about the whole thing, as I really wasn't expecting her to be that much older, but I wasn't going to bail out on her at that point, as that would have in my opinion been extremely rude. We hop in my car and we spend a bit of time together that evening, just talking. I actually did like her on a personal level but the massive age difference and the manner of which I met her made it a bit awkward at first.

We arrive back at her place and she invites me in to hang out more with her, which was fine as I did actually enjoy her company. She made a comment about the cowboy boots I had on and mentioned to me that she owned almost 20 of them. I asked her to show me some of them so she lead me to her bedroom where she had her wardrobe. I sat on the foot of the bed as she was showing me some of her boots and I knew that this was going to lead to something more.

After she was done showing me her boots there was what felt like a long silence and I could feel the tension and anticipation. I initiated by saying "I know this is forward but would you like to have sex?". She thought about it for a couple seconds, mentioned that she liked my approach and then said she would love to.

I started taking my clothes off and she complimented my body as I went down to just underwear. I took off my boxers and when she saw my cock she instantly got on her knees and wrapped her lips around the tip of my cock. She was only able to work with about half of it but she tried to deep throat it to no avail, she later mentioned it was a bit too much. I sort of felt like fucking her but not knowing anything about this woman I decided not to go through with it, so I let her finish me off orally. She swallowed all of my cum and I got dressed.

I hung out with her for a bit longer after that, as I didn't want to just leave awkwardly, before I ended up leaving.

After that she would text me pages every single day, due to wanting more of my cock. She sent me a text saying that she wanted to try to deep throat it, as she saw it as a challenge due to it's size. I did go over one more time for a bj but she became increasingly problematic with the texting over the subsequent days,so wanting to avoid leading her on I mentioned to her I wasn't interested in anything more sexually from her.

Click to expand...

Great story!!
You should have just fucked her good atleast!

SamMann75 said:

My son's class parents hosted a fundraiser for a charity, all dressed up and dinner and drinking and dancing (just the parents no kids), a good time was had by all.

After the event we were walking with another set of parents and the light snow was getting heavier and the wind picked up. The other dad asked where we were parked and as they were closer offered to drive us the extra block to our car. As we live a good hour outside the city I thought about getting a room at the hotel we were passing. They came in and waited to see if we got a room before going along. My wife chatted with them in the lobby as I went to the desk. I got the only room available and returned to our little group and said all they had was a 2 bedroom suite, why don't you come up instead of driving in this? His wife said you have been drinking dear and the roads are not getting better.

When the elevator jolted I think we all felt a little more buzzed then we realized as we all bumped into each other grabbing anything to steady ourselves and pulling each other further off balance...and had a good laugh. This couple was a good 15 years older then us. We got into the suite and I half collapsed into the couch, his petite wife gently sitting beside me as he swept through the room to the floor to ceiling windows commenting on how lavish the room was. He called to my wife who was still standing near the door, then walked over to her saying she had to see this view. He walked her across the room, up the three steps to the area in front of the windows that had a love seat and 2 chairs, and right up to the window. He stood behind her and leaned over her shoulder and softly said isn't the harbor beautiful in the snow? My wife purred, his breath must have been warm on THAT spot behind her ear...he put his hand on her hip...his wife put her hand on my knee and said your wife is truly beautiful...I know I had a conversation with his wife about mine but I can't recall anything I said...I just watched as his hand slid up her side, then slowly lowered the zipper from under her arm on her strapless dress. The dress fell to the floor as he pressed up against her, her hand coming up onto the window near her shoulder, I could see her bare breast pressed against the glass and she gasped and said it's cold and he softly said in her ear and your so hot and then he kissed her neck right behind her ear....his wife now telling me how the moment we showed up tonight he's been talking about what a magnificent dress she was wearing...his hand on her hip I watched his hips press forward and my wife gasped...then the window fogged momentarily as she exhaled and moaned your so big as she pushed her hips back against him. Still gripping her hips he pulled back slowly and pressed forward...further and she moaned your so deep...oh god I need this. His wife said don't worry dear he's not really that big as her hand slid up my leg and grabbed my hardon through my pants...and she leaned into me and whispered ok for her maybe it feels really big as she gave my dick a squeeze. We sat there in silence with her squeezing my dick through my pants as her husband took long slow deep thrusts into my wife, my wife pushing back to meet his thrusts, her body trembling, her legs shaking her moaning loudly the glass fogging around her hands and face and breast pressed up against the glass. We watched as she had two very intense orgasms, and after about 15 minutes he grunted he was going to come and she yes give it to me and she had her third orgasm as he buried himself deep and lifted her off her feet into the window as he came.

When he pulled out my wife turned around and kissed him before getting on her knees and and start cleaning him off. He certainly wasn't big by my wife's standards, but he was better then average and fairly thick. His wife whispered that she'd suggest we take out turn but...and I felt her squeeze my dick...which was no longer hard and felt sloppy. I'm not sure when I came but soon I found myself between her legs giving her oral listening to her husband moan and exclaim in surprise that he was getting hard again. Moments alter I heard my wife grunt and moan...his wife said your wife looks incredibly sexy on all four. I heard my wife grunt again and again and I turned to look over his wife's thigh to see him taking her doggy style, her panties were gone but she was still in the garter belt thigh highs and heels, his pants were around his ankles and his shirt was open as he knelt behind her and was not giving her long hard fast thrust, which she was pushing back against and rolling her hips in what she calls the figure 8. She moaned oh yeah give me that big cock hard, he pulled her hair back and slapped her ass saying you like it rough and she replied I do right now...I felt a hand on the back of my head and I resumed performing oral listening to him pounding away to my wife's enjoyment. After three orgasms (no idea how long) she pulled my chin up to her surprising firm stomach, I laid my head on her stomach watching my wife now on top of him riding him with her breasts in his face. For 40 minutes I laid between her legs on the couch, my head on her stomach her hand playing with my hair and her foot rubbing my hard again cock watching our spouses fuck in several positions, my wife having several orgasms before he came in her again. About 10 minutes before they ended his wife said goodness he's going to have to go back to the chiropractor after your wife's done with him..and with her foot rubbing my cock through my pants I came again.

After they finished and were just laying on the floor breathing heavy she stood me up, letting her dress fall off she took my hand and wearing just bra and panties led me to the bathroom, undressed me and cleaned my off with a warm face cloth before rinsing my underwear in the sink and hanging them up to dry. She took the hotel robe and put it on me and led me back out to the couch and sat on my lap, started telling me how incredibly sexy the two of them looked together. He was laying flat on the floor and my wife was once again seeing to the cleanliness of his softened cock. Licking and sucking it gently, her nipples looked swollen I don't think I've ever seen them so big. I think it was a surprise to us all as he started to stiffen again. He said are you up for it, my wife said I might never get the chance again as she climbed up his body and onto him. They were gentler this time, a few short periods of hard and fast but mostly gentler. In the light as they changed positions I noted how red my wife's ass was, and there were marks all over her breasts as I remembered he had sucked on them a lot during their second round.

The next morning he joined my wife in the shower and then we left and went to our separate homes. We see them at school all the time and talk like old friends. We've never done anything since, we've never even talked to them about it since. It's like it never happened.

Click to expand...

Great story! Thank you for sharing this!

Many years back I was the day manager at a grocery store and it was my job to let the deli crew in at 5am. One morning I opened up as usual and went back to my car to get something and a friend of mine pulled up next to me. He had been drinking all night with his wife at home and she had passed out. He told me she was suppose to give him a blow job but she didn't get around to it before she feel asleep. He was obviously horny as hell and hinting heavily that I should suck him off. We were very good friends and I had lusted after his dick for years but with no luck because he was straight. There was one time we both were really drunk and I felt him up after he passed out but he woke up long enough to tell me to stop.

So here was my chance to see and play with his dick if I decided to do it. I watched as the deli crew as they went inside and told my friend to wait there that I would be back. I went inside and checked on the crew and took the phone off the hook so they wouldn't have to answer the phone. I then went back outside and over to me friends car where I found him passed out and his pants around his feet. His dick was rock hard and he was dripping precum. I reached in and slowly wrapped my hand around his dick. I tugged on it some and collected his precum and put it up to my mouth. His hand moved over and unlocked the doors, never opening his eyes.

I though oh shit I'm going to get fired but I was being invited to service a friend I've wanted for years and he was ready. I went around the car and got in on the passenger side and shut the door. I waited until the interior lights had gone off and I went down fast onto his dick. Sucking hard and massaging his balls to release his man juice. I was in a hurry so I had to work fast. I had never sucked that hard before but I was determined to get his load. Then I felt his stomach jerk and his balls got tight. He then moaned loudly as he pumped his cum in my mouth and there was a lot of it too. I swallowed like a mad man making sure I didn't miss any. I sat back up and wiped my lips as he started to open his eyes. He smiled at me and pulled his pants back up. He thanked me and kissed me on the check and told me to have a nice day. He drove off and I made it inside the store before the other manager showed up. I went straight to the bathroom and quickly jacked off as I tasted his cum in my mouth..........

SamMann75 said:

My son's class parents hosted a fundraiser for a charity, all dressed up and dinner and drinking and dancing (just the parents no kids), a good time was had by all.

After the event we were walking with another set of parents and the light snow was getting heavier and the wind picked up. The other dad asked where we were parked and as they were closer offered to drive us the extra block to our car. As we live a good hour outside the city I thought about getting a room at the hotel we were passing. They came in and waited to see if we got a room before going along. My wife chatted with them in the lobby as I went to the desk. I got the only room available and returned to our little group and said all they had was a 2 bedroom suite, why don't you come up instead of driving in this? His wife said you have been drinking dear and the roads are not getting better.

When the elevator jolted I think we all felt a little more buzzed then we realized as we all bumped into each other grabbing anything to steady ourselves and pulling each other further off balance...and had a good laugh. This couple was a good 15 years older then us. We got into the suite and I half collapsed into the couch, his petite wife gently sitting beside me as he swept through the room to the floor to ceiling windows commenting on how lavish the room was. He called to my wife who was still standing near the door, then walked over to her saying she had to see this view. He walked her across the room, up the three steps to the area in front of the windows that had a love seat and 2 chairs, and right up to the window. He stood behind her and leaned over her shoulder and softly said isn't the harbor beautiful in the snow? My wife purred, his breath must have been warm on THAT spot behind her ear...he put his hand on her hip...his wife put her hand on my knee and said your wife is truly beautiful...I know I had a conversation with his wife about mine but I can't recall anything I said...I just watched as his hand slid up her side, then slowly lowered the zipper from under her arm on her strapless dress. The dress fell to the floor as he pressed up against her, her hand coming up onto the window near her shoulder, I could see her bare breast pressed against the glass and she gasped and said it's cold and he softly said in her ear and your so hot and then he kissed her neck right behind her ear....his wife now telling me how the moment we showed up tonight he's been talking about what a magnificent dress she was wearing...his hand on her hip I watched his hips press forward and my wife gasped...then the window fogged momentarily as she exhaled and moaned your so big as she pushed her hips back against him. Still gripping her hips he pulled back slowly and pressed forward...further and she moaned your so deep...oh god I need this. His wife said don't worry dear he's not really that big as her hand slid up my leg and grabbed my hardon through my pants...and she leaned into me and whispered ok for her maybe it feels really big as she gave my dick a squeeze. We sat there in silence with her squeezing my dick through my pants as her husband took long slow deep thrusts into my wife, my wife pushing back to meet his thrusts, her body trembling, her legs shaking her moaning loudly the glass fogging around her hands and face and breast pressed up against the glass. We watched as she had two very intense orgasms, and after about 15 minutes he grunted he was going to come and she yes give it to me and she had her third orgasm as he buried himself deep and lifted her off her feet into the window as he came.

When he pulled out my wife turned around and kissed him before getting on her knees and and start cleaning him off. He certainly wasn't big by my wife's standards, but he was better then average and fairly thick. His wife whispered that she'd suggest we take out turn but...and I felt her squeeze my dick...which was no longer hard and felt sloppy. I'm not sure when I came but soon I found myself between her legs giving her oral listening to her husband moan and exclaim in surprise that he was getting hard again. Moments alter I heard my wife grunt and moan...his wife said your wife looks incredibly sexy on all four. I heard my wife grunt again and again and I turned to look over his wife's thigh to see him taking her doggy style, her panties were gone but she was still in the garter belt thigh highs and heels, his pants were around his ankles and his shirt was open as he knelt behind her and was not giving her long hard fast thrust, which she was pushing back against and rolling her hips in what she calls the figure 8. She moaned oh yeah give me that big cock hard, he pulled her hair back and slapped her ass saying you like it rough and she replied I do right now...I felt a hand on the back of my head and I resumed performing oral listening to him pounding away to my wife's enjoyment. After three orgasms (no idea how long) she pulled my chin up to her surprising firm stomach, I laid my head on her stomach watching my wife now on top of him riding him with her breasts in his face. For 40 minutes I laid between her legs on the couch, my head on her stomach her hand playing with my hair and her foot rubbing my hard again cock watching our spouses fuck in several positions, my wife having several orgasms before he came in her again. About 10 minutes before they ended his wife said goodness he's going to have to go back to the chiropractor after your wife's done with him..and with her foot rubbing my cock through my pants I came again.

After they finished and were just laying on the floor breathing heavy she stood me up, letting her dress fall off she took my hand and wearing just bra and panties led me to the bathroom, undressed me and cleaned my off with a warm face cloth before rinsing my underwear in the sink and hanging them up to dry. She took the hotel robe and put it on me and led me back out to the couch and sat on my lap, started telling me how incredibly sexy the two of them looked together. He was laying flat on the floor and my wife was once again seeing to the cleanliness of his softened cock. Licking and sucking it gently, her nipples looked swollen I don't think I've ever seen them so big. I think it was a surprise to us all as he started to stiffen again. He said are you up for it, my wife said I might never get the chance again as she climbed up his body and onto him. They were gentler this time, a few short periods of hard and fast but mostly gentler. In the light as they changed positions I noted how red my wife's ass was, and there were marks all over her breasts as I remembered he had sucked on them a lot during their second round.

The next morning he joined my wife in the shower and then we left and went to our separate homes. We see them at school all the time and talk like old friends. We've never done anything since, we've never even talked to them about it since. It's like it never happened.

Click to expand...

wow awesome

Daddy Bear said:

Many years back I was the day manager at a grocery store and it was my job to let the deli crew in at 5am. One morning I opened up as usual and went back to my car to get something and a friend of mine pulled up next to me. He had been drinking all night with his wife at home and she had passed out. He told me she was suppose to give him a blow job but she didn't get around to it before she feel asleep. He was obviously horny as hell and hinting heavily that I should suck him off. We were very good friends and I had lusted after his dick for years but with no luck because he was straight. There was one time we both were really drunk and I felt him up after he passed out but he woke up long enough to tell me to stop.

So here was my chance to see and play with his dick if I decided to do it. I watched as the deli crew as they went inside and told my friend to wait there that I would be back. I went inside and checked on the crew and took the phone off the hook so they wouldn't have to answer the phone. I then went back outside and over to me friends car where I found him passed out and his pants around his feet. His dick was rock hard and he was dripping precum. I reached in and slowly wrapped my hand around his dick. I tugged on it some and collected his precum and put it up to my mouth. His hand moved over and unlocked the doors, never opening his eyes.

I though oh shit I'm going to get fired but I was being invited to service a friend I've wanted for years and he was ready. I went around the car and got in on the passenger side and shut the door. I waited until the interior lights had gone off and I went down fast onto his dick. Sucking hard and massaging his balls to release his man juice. I was in a hurry so I had to work fast. I had never sucked that hard before but I was determined to get his load. Then I felt his stomach jerk and his balls got tight. He then moaned loudly as he pumped his cum in my mouth and there was a lot of it too. I swallowed like a mad man making sure I didn't miss any. I sat back up and wiped my lips as he started to open his eyes. He smiled at me and pulled his pants back up. He thanked me and kissed me on the check and told me to have a nice day. He drove off and I made it inside the store before the other manager showed up. I went straight to the bathroom and quickly jacked off as I tasted his cum in my mouth..........

Click to expand...

Interesting. Did you two ever get together again?

Recent experience with a married guy who only had a picture of his beautiful cock as his profile picture. He hit me up first. Of course I'd seen his profile many times because he's in my area so his profile comes up next to mine often. He introduced himself and told me he was happily married and he was interested in meeting someone close for regular encounters. He told me he and his wife enjoyed kink and his wife encouraged him to reach out to me to see if I'd be interested in coming to their house and giving him a blowjob while she watched. He clearly stated that she wasn't interested in anything more and she would only be a set of eyes as it gets her off seeing gay guys sucking him off. This was a new experience for me and I had to think about it but figured what the heck. I took a chance and went to their house we chatted had some drinks and went straight to work. They told me they got turned down a lot by gay guys because of his wife being present. I told them I was hesitant at first but after they explained their unique fetish I felt it was cool and decided to do it. I sucked him off while he was reclined in a chair while his wife sat over to the side playing with her clit and nipples. His eyes were glued to her playing with herself and occasionally he'd allow himself to look down at me going to work. I noticed his eyes rolling back from time to time and that really got his wife going. Didn't take very long before he was gripping the side of the chair and his body was getting rigid. He yelped out that he felt like he was about to cum so I continued. I was alternating between sucking his thick cock and sucking and massaging his balls and he was loving his balls being sucked just as much as he was enjoying my tongue roiling around the head of his cock and along his shaft. I went down to suck his balls again thinking I had plenty of time before his load would shoot forth. My timing was a bit off because once I was on the balls he shot the biggest load up into the air and it landed on the both of us. I realized his cock was viciously bobbing and spitting so I tried to coral it again with my lips as it shot spurt after spurt of warm cum into the air. I managed to wrangle it on the last 2 squirts so that I could enjoy the thick baby batter that was to be my reward. He was coming down from his intoxicating euphoria with his cock gently throbbing against my tongue when his wife squealed and started to squirt from her vagina just as he was finishing up. They both got off and that was a first for the both of them. His wife had never squirted before and was quite shocked by her own body's reaction at it's height of sexual arousal. I think she scared herself and her husband had a huge smile on his face. He thanked me for being the fist man to make his wife cum without even touching her. It was such a wonderful experience and we will be meeting up on a regular basis now to try to duplicate that experience.

I went out one night with one of my friend’s wife as we would normally do. On our drive to the hotel where we were planning on staying, she mentions that she was having problems with her husband and how they haven’t been having sex and was really horny. I laughed and brushed it off. We ended up hitting a couple of bars and we ran into three other guys that we knew from work. They joined us and we continue drinking and just dancing. Well two of the guys that we ran into wanted to go home and the third guys said he wanted to stay longer, so we told him we booked a hotel not far away and we are driving back tomorrow and told him he could stay with us. So, he decided to crash with us, so we grabbed some pizza before heading back to the hotel. When we got back to the hotel, I grabbed a pizza and saw the other two go into the bathroom. I was going to go to bed, but I had to pee, so I knocked at the bathroom and told them I had to pee and when inside. I saw that our other friend passed out naked sitting on the toilet. I looked at her and she was laughing. I pee in the shower and left the bathroom and when I left the bathroom she followed as well. She got into bed and said I like to cuddle, and I said okay that fine. So, we got into bed and I put my arms around her, and she asked me to take my pants off. She began rubbing against me and I slide her panties to the side and began to rub on her pussy. She then put her hand inside my underwear and began to jerk me off. We were kissing and I took my boxers off and she began to suck me off. I was hard rock by this time, so I push her down and grabbed her legs and push her towards me getting ready to slide in and then our friend that was passed out came out of the bathroom and saw us. He came closer and sat on the bed and she grabbed his hand and put it on her tits. I took it as she wanted him to join, so I grabbed my dick and started rubbing my head against her pussy lips. I started going in when he said stop!!! We can’t do this and stopped the whole thing from going any forward. We got dressed and she went to the other bed by herself. Well we went to bed and about 20 minutes later when he passed out, she called for me, so I got out of bed and went into hers. It didn’t take much for me to get a hard on. I got on top of her took her panties off again and I waited no time and put my dick inside her. We try really hard not to make much noise, I had my hands over her mouth because I was trying to cover her moans and it made it more exciting that we were trying to get caught. We probably fucked for a good 40 minutes and then when we finish, I put my boxers back on and went back to my bed.

Cockychris said:

Mine would have to be with college roommate, I know a lot of us experiment in college but certainly wasn't on my list of things to do.

Click to expand...

I wanna hear all about it? What did you and your roommate do?

After my wife and I separated ,I stayed a month with a bandmate that I hired to work for the shop I was . He wasn't very skilled at anything. The boss paid him a small wage and I was training him to help me. I was paying him extra if he helped with my commission jobs.
He had a new baby and they were tight on funds. I knew his gf very well ,so it worked well until I knew my next move. I wasn't there much and paid WELL.
I needed relief and didn't want to disrespect by jacking in common area where I could be seen by his gf. She had seen before ,but he was not aware and he was pretty insecure. I wouldn't use the bathroom in the child's room. Just felt creepy. SO, I got my portable dvd player and was sitting at the table on the secluded patio where they smoked. It was late and she was crashed.
He came out to smoke upon hearing me. I was dressed but had porn queued . He wanted to borrow it and I told him I was needing it. He pushed and I said " watch it here" and told him" Im not gonna mess with ya". I stood and dropped my pants, and he said" Damn, you pack heat" . A lil snicker and I thought no more of it. After a few mins I noticed that he wasn't watching the porn. He was watching me. He got embarrassed when I noticed ,and I told him that it was no big deal. I told him he was very welcome to look all he wanted. I didn't go into great detail ,but I told him that I have jacked with buds before . He said " Wow, really?" I said " yeah, it is nice that you want to look ,and I like jacking off with friends" I turned my chair towards him so he had a better view. He said" Damn, that is a really big cock, bro" I said " thanks" He said " No, thank you".
He was very curious about the jacking and asked if we had certain rules. I said" Show respect and enjoy yourself together. He asked" has anyone ever touched your dick when you jacked with them". I said" of course". His jaw dropped and before he said a word I asked" Do you want to touch my cock?"
He got wide eyed and asked" are you being serious?" I said" If you want to I want you to". He said" I don't want to seem like I am totally gay ,but big dicks are my secret fetish and this is a basically a fantasy for me". He grabbed my cock and it was about half erect. He said" Damn, this is so hot". He stroked me and put both hands on it. His cock was standing straight up,and it had a little oozing out. He got me pretty hard and I rubbed it against his cock. His jumped and he moaned.
I held mine against his and jacked us both.
He leaned back and said " Ohhh fuck" and the cum shot once then oozed. It spurted and flowed over my hand and down our dicks. I stood up and rabbit jacked my cock and came on his still hard dick.
He got embarrassed after he came and it was a little awkward. The next day he went to play golf out of town with his dad.
I was laying in the sun with headphones. His girl took the kid to his mom's and I didn't know she was back. She sat by me and said" I got up to get a drink and saw you two out the kitchen window".
I was unsure what to say. She said" He really needs someone to help him with his sexual identity issue". I asked her" what do you mean?" She informed me that her pc was acting up and discovered that he was looking at naked men and some gay videos. She said" he has a couple vhs tapes under the sofa. She told me she asked him if he had been with any guys. He said " no, just porn ,and that he was just comparing and was kind of curious,but wasn't no fag". She said " it is ok if that turns you on,just don't go behind my back". I told her what we did and how it came to be. She said" I am glad it was your and that he didn't go to some truck stop or craigslist's". She told me that he is very insecure and thinks he is too small. She said she tells him he is plenty for her,but he doesn't believe her. I told her he was obsessed with mine ,and kept telling me it was huge. She said" It is". She told me that she saw it hard last night, and thought" omg".
I was wearing a pair of white Jockey Life bikini briefs as I tanned. The sweat and oil had them pretty transparent. I went for my tshirt to cover myself ,because I didn't have a towel. She said" it's ok,Im not bothered at all. You can wear that all day". When my hand touched my dick I realized that it was sunburned.
Pretty bad too. She laughed a little at first,but when she realized that it was as bad as it was she got concerned. I went to the shade and sat. She asked" how bad is it?"
I said" I don't know, but it hurts".
She said" Well look". I pulled my underwear down and it was pink with a red stripe of bad burn. She said " Ohhh no".
She went in and got her Noxema.
She asked" have you used this before?" I said " no". She said" I am going to put this on. don't freak".
She gently coated my dick with it ,and commented how her hand wouldn't go all the way around it. She said" I will go to Walgreens for aloe burn gel". I waited nude for her. She got back and put it in freezer to cool for a bit. When she put it on it was cold and I flinched. She said" ooops, did I hurt ya or is it just cold?" I said" very cold". She filled her hands and warmed it a little ,but the cool was soothing. She put a few coats on and it started to plump me up a bit. She said" Keep that thing under control...and giggled " It got half hard in her hand, and she said" you do have a really big dick". "Does this hurt?"
she asked. I said" no, it feels good".
She filled her hand again and stroked me. I got fully hard and she kept on. She got a little faster,and I came on my chest. She said" I didn't do anything he didn't. Then winked. The next few days I healed.
The next weekend I got a suite at the casino. She confronted him and had him come to play with me. She told him that he needed to work out every curiosity that he had to see how he really felt about things. She got it started. She said" I am gonna take a long hot bath,and you two have fun.
We jacked and sucked. She joined. She taught him how to deep throat. He came in my mouth. I came in both of theirs. It was a good time, but his jealousy ended up costing the friendship. Well, for a few years anyway... He calls occasionally to play if I am up for his company.

It wasn’t “sexual” (at least by Bill Clinton’s standards), but it was just this last weekend, and it was pretty fun.
So for various reasons my partner and I spent thanksgiving holiday with our separate families. I went to a cousins house in Oregon for long weekend. A nephew who was there had just gotten engaged, so five of us guys went to my cousin and her husband’s cabin for a couple days skiing while the women stayed in town and did wedding stuff. It was myself, my cousin's husband (their cabin), my nephew, the furniture brides father, and her brother. It is a four bedroom cabin, one bedroom had a pair of twin beds so to let the guys who were newer to the family have their own rooms my cousins husband, Daniel, and I shared the room with twin beds.
I’ve known Daniel since they married in about 1990, so almost 30 years. He is a very athletic jock type guy, always playing some sport, coaching, backpacking, camping, etc. He’s always been very nice, but I’ve always been very close to my cousin and we’d often travel or do things just the two of us while Daniel was off doing his own thing (he was probably glad to have someone take her off his hands for a while). Point is, over 30 years I haven’t really spent that much time with him.

Daniel is a jock, tech nerd, never had children.....one of those guys who is very blunt and matter of fact in conversation and often has a locker room filter on what he says. I think he is just so used to only being around only guys, or just his wife. He’s not a shy guy, hot tubbing in the nude, pisses with the bathroom door open, and he doesn’t seem to realize most people aren’t that nonchalant.

Anyway, five of us are up at the cabin, Daniel and I sharing a room. First night he walks down the hall, naked, and into the master bedroom (which is where is clothes are and the future father-in-law is staying) to get a pair of sweatpants. Doesn't knock, startles the old guy and freaks him out a bit I think, lol. I hear all the commotion and come into our shared room, Daniel announces he's going to turn in, wants to start skiing early, blah blah. I'm clearly looking at him and he says, "oh yea, I still sleep in the raw, doesn't bother you does it? " I say of course not, blah blah that I didn't bring anything to sleep in either.

Over the years I've seen Daniel naked several times (hot tub, changing clothes, and in lockerroom), and he was much more of a grower than a shower, and still appears to be. One of the first times when he saw me naked also was years ago right after they were married, I went golfing with he and his dad and brother. In the lockerroom after I came out of one side of showers and he the other, my dick swinging to and fro, his more just sticking out kind of bobbing. He never really said much at the time, but there have been quite a few instances where reference was made to my cock over the years, so I know he told his wife that I at least hung low. It has been almost 30 years since that, he is still in very good shape, basically a 62 year old jock, bald now, and his body hair has gone salt and little pepper, but his cock hasn't changed much as I remember.

So in the morning, sun just coming up, I'm startled awake by this fap, fap, fap and I sit up in bed and see Daniel is jerking off! "what the ….." I say as I sit up, he just looks at me and says "I can't very well rub one out in the shower, almost gave the old guy a heart attack last night, he'd never get over this (he chuckles with a fist full of cock), day's just not right if I don't start it off right, you know." I see he has his tablet laying on the bed, probably watching porn, and I'm startled but not really that startled because he is just so nonchalant about stuff. I stand up with a bit of a morning chubby, pull on some pants (while checking out his cock of course), and say "I'll go make coffee and let you finish your work here". As I'm making coffee thinking about his cock, (not bad but I've definitely got him beat in the size department) I'm trying to figure out how I should respond or react. He clearly knows I'm gay, and he has never had an issue with that or been the least bit homophobic, always treating me just like one of "the guys". I decide I'll be just as nonchalant as he, acting like it was an everyday occurrence. When he finally comes out, he mumbles something about sorry for waking me up, and how as we get older we go back to our childhood …. that we used to jack off a lot as kids, then when we get older out wives don't want sex so we end up jacking off a lot again as older men. I say that I see his point and that I guess I kind of agree, to which he walks over, gives me a lockerroom-type punch at the chest and says, "yea, you're just like the rest of us …..maybe worse." He grins and heads out to ski, saying to txt him when we all head up.

Turns out the future in-laws aren't much for snow skiing, they're from Florida, after about 4 hours they were done. That night the two younger guys went into town to hit a few bars, the father was pretty sore (he was in pretty good shape, but closer to 70 I think) so Daniel suggested he take a soak in the hot tub after dinner. Daniel cleaned up the kitchen and I went into the bedroom and made a few phone calls and checked email. Pretty soon Daniel comes in starts stripping off says he's going out, tells me to grab a beer and beer and join them. I said I didn't bring any trunks and didn't he think he should put some on since he had guests and all? His response was typical, "huh...…?... we're all guys.....?.....I don't know ANYONE who wears trunks in the hot tub, even in mixed company!...….you're so uptight, relax" as he struts down the hall naked toward the back door. I think about this for maybe 10 minutes, decide it's his house so who am I to correct him, and figure I'll go out and say hi. I step out, ask if I can get anybody a beer and make a bit of small talk. I can see Daniel's dark bush in the water (clearly he didn't opt for trunks) and it looks like maybe the father has on tighty whities. They both tell me to grab a beer and join them, the father sounding rather insistent, so I agree thinking he's a bit uncomfortable with just the two of them. They have a small cooler of beer outside so I've no reason to go back in, as I pull off my shirt I realize I'm commando so its going to be au natural for me as well......I can either be a prude and say I've got to go in for some underwear or follow my hosts lead and go for it...… Daniel must have sensed my slight hesitation and says, "just strip off and hop in, the water is great". I'm much more of a shower than Daniel, and there was a time I'd have been more reserved around people I didn't know, now I just went for it leisurely stripping off pants and flopping back and forth as I pulled off socks (probably standing there just a little longer than necessary). We soaked and talked about the upcoming wedding, their families, blah, blah, finally the father got out for another beer and could see he filled out his fruit of the looms pretty well, but he wasn't taking them off. He took a towel and announced he was going to bed, about 20 minutes later I was really fading so wrapped a towel around my waist and headed for bed also.

guess I was over the 1000 character limit ……. here is rest

Mike

This is a true recount of an unexpected encounter which resulted in a true friendship. I have changed his name, however everything else is as it happened. Please excuse the 'length', ahem...

I've had a few 'unexpected' encounters, but one that always brings a smile to my face was around 6 years ago, and which, incidentally is in running as biggest dick I have encountered, but I'll come onto that. It involves a guy who has since passed away and I'll always treasure the memory of us and our friendship.

Around springtime 6 years ago I'd just moved into a new apartment and over the course of the next few weeks, met and got to know my new neighbours. One of them was an older guy, Mike, late 60s (later confirmed as 68yo), lived on his own. He was what you would describe as a 'rough diamond', you could tell by the way he spoke and his appearance that he had certainly lived a life. That's not to be unkind, that's just the way he was. He'd sometimes stopped to speak, he was friendly enough but you got the impression that you wouldn't want to get on the wrong side of him.

Anyway Spring turned to Summer and I had settled into my new apartment. I had a rare weekday off and it was warm out so after gym and a few chores I decided to relax in the communal back yard with some beers. I changed into some jogger shorts and a t-shirt and went out back. I always free-ball in shorts in summer and today was no exception, love the feeling of my cock and balls hanging loose and always show a good bulge in the jogger shorts

So I put some beers into a cooler and headed down into back yard. On the way down I bumped into Mike and said I was headed out back for some beer in Sun and he was welcome to join me. He thanked me and said he'd join me after he done some chores, I replied in the affirmative and headed out.

Around half hour later Mike appeared carrying some beers and sat down at the table next to me. He was wearing some longer knee-length shorts and a wife beater. It was the first time I'd actually seen him show any body, and I was pleasantly surprised. He was much shorter than I, barely above 5' tall (actually 5'2"), but had a lean muscled body that a guy half his age would kill for. You could tell he obviously kept himself in shape when he was younger through manual work and at 68yo had the body to show for it. We sat and shoot the shit over the beers and I found out more about him. He had been a coal miner (hence the body) and worked at a builders merchant when the mine had closed down. He had been married around 22yo, no kids, and his wife had unfortunately died 10 years back and he'd been living on his own ever since. I commiserated with him and he acknowledged and said he would always love her. I told him I’d not long broken up with my ex-boyfriend and was just content enjoying single life. There was momentarily shock on his face the he grinned and said there’s nothing new under the sun, your only young once lad, swigging back the beer.

Conversation turned to the apartment block and how I enjoyed the area. I said it seemed a nice area and the neighbours are pretty friendly so so far so good! He laughed and cheered my beer. He then asked me if I heard the woman in the apartment between our apartments, (she is quite the screamer!)

I burst out laughing and said 'Mate, you can't fail to hear her, although I give as good as I get!" (I am pretty vocal!) He hollered with laughter and said he hadn't heard me. He proceeded to tell me that he'd had a drunken one-nighter with our loud neighbour the year before but that was all it was as he 'broke her' as he put it. It was my turn to burst out laughing, ‘Mate, your like the gable-end of a £5 note, there’s nothing of you, and she’s a big lass!’ He laughed back saying that he was hung like a horse. I laughed it off saying ‘Yeah right mate, whatever!’ There was silence and he then got serious and said ‘come into my apartment and I’ll show you’ and then got up and headed inside. The beers obviously had an effect on both of us as I followed him a few seconds later. I followed him into his apartment and closed the door behind me.

He then stood in middle of his hallway and asked me if I was ready. I was still laughing and said sure, show me what you’ve got! He dropped his shorts and I realised why they were knee length! Hanging limp between his lean legs was thick 6” dick. That’s big soft, but on his short stature it looked freakishly huge! I was gobsmacked and then I remembered myself and went ‘Fucking hell mate you weren’t joking, no wonder you broke her!’ He laughed and said ‘that’s nothing, watch!’ He picked up a ruler with one hand and he proceeded to jerk it a few times with the other until it was a 3/4 hard at nearly 10”. He said at his age that’s all he can usually manage, but rock hard it’s nearer 11"!

He then asked me if I was enjoying the show and nodded to my shorts, which were now tented out and getting soaked with pre. I hadn’t even realised I was rock hard myself! Mike then said ‘Go for it lad. We both need it!’

I didn’t need telling twice. I got on my knees and throated that huge hog of his like my life depended on it. It was the biggest I’d taken in a while and I gagged a couple of times but kept on going. Mike just kept a hold of my head and groaned. After a few minutes of worshipping his horse cock he let out a guttural moan which grew louder and he started pumping what felt like a gallon of cum down my throat. His dick then went limp and I had to physically catch him as he fell back. Once we caught out breath he gasped it had been a while. He then got all serious and started getting dressed, telling me no one can know and keep it between us. I gently reassured him and he told me I was a good lad and said we’d do this again.

Over time we got into a routine, he’d leave a pair of shoes outside his apartment door and that was my signal to come on in and drain his huge hog of a dick. I still marvelled at it’s size as it just looked obscene on his short 5’2” stature! He reciprocated a few times but he was just as happy to sit back and let me take care of him. We became good friends and I helped him out around his apartment with tasks he couldn’t do anymore. As time went on he opened up more about his past. He’d had some man-on-man experience when he was in his teens, but in the late 1950s early 1960s it just wasn’t accepted. When he met his future wife he put it out of his mind and never strayed all the time they were married. As he got older the ‘fun’ subsided but I always called in for a catch-up and looked out for him. Last summer he took ill and was confined to hospital. I was due to go on holiday and called into the Hospital to see him. He was in good spirits, and we talked about life in general, but you could tell he was fading. When visiting was over, he grabbed my arm and looked into my eyes and thanked me for my friendship. I held his hands and told him it had been a pleasure and left.

I had a phone call from the hospital the day before I was due to come home telling me he had passed. I will never forget him.

That is really fucking hot man. I had a similar thing happen when I was younger. Still beat off to that memory hahaha

Pornsword1 said:

After my wife and I separated ,I stayed a month with a bandmate that I hired to work for the shop I was . He wasn't very skilled at anything. The boss paid him a small wage and I was training him to help me. I was paying him extra if he helped with my commission jobs.
He had a new baby and they were tight on funds. I knew his gf very well ,so it worked well until I knew my next move. I wasn't there much and paid WELL.
I needed relief and didn't want to disrespect by jacking in common area where I could be seen by his gf. She had seen before ,but he was not aware and he was pretty insecure. I wouldn't use the bathroom in the child's room. Just felt creepy. SO, I got my portable dvd player and was sitting at the table on the secluded patio where they smoked. It was late and she was crashed.
He came out to smoke upon hearing me. I was dressed but had porn queued . He wanted to borrow it and I told him I was needing it. He pushed and I said " watch it here" and told him" Im not gonna mess with ya". I stood and dropped my pants, and he said" Damn, you pack heat" . A lil snicker and I thought no more of it. After a few mins I noticed that he wasn't watching the porn. He was watching me. He got embarrassed when I noticed ,and I told him that it was no big deal. I told him he was very welcome to look all he wanted. I didn't go into great detail ,but I told him that I have jacked with buds before . He said " Wow, really?" I said " yeah, it is nice that you want to look ,and I like jacking off with friends" I turned my chair towards him so he had a better view. He said" Damn, that is a really big cock, bro" I said " thanks" He said " No, thank you".
He was very curious about the jacking and asked if we had certain rules. I said" Show respect and enjoy yourself together. He asked" has anyone ever touched your dick when you jacked with them". I said" of course". His jaw dropped and before he said a word I asked" Do you want to touch my cock?"
He got wide eyed and asked" are you being serious?" I said" If you want to I want you to". He said" I don't want to seem like I am totally gay ,but big dicks are my secret fetish and this is a basically a fantasy for me". He grabbed my cock and it was about half erect. He said" Damn, this is so hot". He stroked me and put both hands on it. His cock was standing straight up,and it had a little oozing out. He got me pretty hard and I rubbed it against his cock. His jumped and he moaned.
I held mine against his and jacked us both.
He leaned back and said " Ohhh fuck" and the cum shot once then oozed. It spurted and flowed over my hand and down our dicks. I stood up and rabbit jacked my cock and came on his still hard dick.
He got embarrassed after he came and it was a little awkward. The next day he went to play golf out of town with his dad.
I was laying in the sun with headphones. His girl took the kid to his mom's and I didn't know she was back. She sat by me and said" I got up to get a drink and saw you two out the kitchen window".
I was unsure what to say. She said" He really needs someone to help him with his sexual identity issue". I asked her" what do you mean?" She informed me that her pc was acting up and discovered that he was looking at naked men and some gay videos. She said" he has a couple vhs tapes under the sofa. She told me she asked him if he had been with any guys. He said " no, just porn ,and that he was just comparing and was kind of curious,but wasn't no fag". She said " it is ok if that turns you on,just don't go behind my back". I told her what we did and how it came to be. She said" I am glad it was your and that he didn't go to some truck stop or craigslist's". She told me that he is very insecure and thinks he is too small. She said she tells him he is plenty for her,but he doesn't believe her. I told her he was obsessed with mine ,and kept telling me it was huge. She said" It is". She told me that she saw it hard last night, and thought" omg".
I was wearing a pair of white Jockey Life bikini briefs as I tanned. The sweat and oil had them pretty transparent. I went for my tshirt to cover myself ,because I didn't have a towel. She said" it's ok,Im not bothered at all. You can wear that all day". When my hand touched my dick I realized that it was sunburned.
Pretty bad too. She laughed a little at first,but when she realized that it was as bad as it was she got concerned. I went to the shade and sat. She asked" how bad is it?"
I said" I don't know, but it hurts".
She said" Well look". I pulled my underwear down and it was pink with a red stripe of bad burn. She said " Ohhh no".
She went in and got her Noxema.
She asked" have you used this before?" I said " no". She said" I am going to put this on. don't freak".
She gently coated my dick with it ,and commented how her hand wouldn't go all the way around it. She said" I will go to Walgreens for aloe burn gel". I waited nude for her. She got back and put it in freezer to cool for a bit. When she put it on it was cold and I flinched. She said" ooops, did I hurt ya or is it just cold?" I said" very cold". She filled her hands and warmed it a little ,but the cool was soothing. She put a few coats on and it started to plump me up a bit. She said" Keep that thing under control...and giggled " It got half hard in her hand, and she said" you do have a really big dick". "Does this hurt?"
she asked. I said" no, it feels good".
She filled her hand again and stroked me. I got fully hard and she kept on. She got a little faster,and I came on my chest. She said" I didn't do anything he didn't. Then winked. The next few days I healed.
The next weekend I got a suite at the casino. She confronted him and had him come to play with me. She told him that he needed to work out every curiosity that he had to see how he really felt about things. She got it started. She said" I am gonna take a long hot bath,and you two have fun.
We jacked and sucked. She joined. She taught him how to deep throat. He came in my mouth. I came in both of theirs. It was a good time, but his jealousy ended up costing the friendship. Well, for a few years anyway... He calls occasionally to play if I am up for his company.

Click to expand...

About four years ago at a gig. Was a bit drunk, and there was some very friendly drunk guy in front of me. Thought he kinda looked like someone I know. Anyway he’s a very happy chap, and at one point randomly gives me a kiss on the cheek. I turn to him and give him a full on snog. It carries on like that for five minutes, then we go to the toilets. We’re making out, then I’m sucking him off/feeling his ass as I blow him. He doesn’t cum in my mouth, but kinda finishes? We then just sit there and chat for a bit, then we almost got thrown out! We’d been in there so long they thought we were doing drugs or something (we weren’t). After that we went back to the gig, continued making out the entire night. At the end of it he wanted to go out throughout the night and I kinda wish I had, cos I saw him once after this but when speaking to him it never went anywhere. But tbf I needed to get home and I’m glad I did cos after that I bumped into a guy from my town and now he’s one of my best buds so there’s that too