Strangest sexual encounter

This was strange to me at least…

I had broken up with my ex, and tried in vain to move on. We argued a lot, as she wanted my bank account back (not so much me) and I wanted no part to do with her. I thought I had taken all of my things from her place, when out of the blue she messaged me saying she found some clothes of mine. We were angry on the phone, calling each other names and swearing. I lost my temper and said “Fine, I will be by tonight and get them!”

When I arrived , her co workers were sitting on her couch. She led me into her bedroom, where she pointed out some male underwear (not mine), alongside her lingerie I bought her, and a few sex toys. I said “None of this is mine.”

She kind of shrugged, pushed me on the bed, and suddenly my pants and underwear were around my ankles and she was sucking me off like her life depended on it.

Here I was, laying beside some guys underwear on one side, lingerie and a dildo on the other, and her bedroom door open so the co workers could hear.

Granted, I did blow my load and she swallowed and said “Sorry I thought this stuff was yours.” I left under the watchful eyes of her co workers and my ex said “Go fuck yourself” as I was walking out.

It all seemed kind of strange to me…

Wow, she really showed you! Lol.
 
I watched her for for a short time I could plainly hear her pussy juices as she was fingering herself i moved and saw her fingers sliding up and down her pussy I just lost it threw her on her knees and banged away till I cum again up that beautiful hairy pussy wich was allready dripping with cum I collapsed next to her I was truly fucked but she started to tell me hurry up I had to leave we'd took too long literally pushing me out the bed anyway after ide dressed and she was pushing me out of the door she kissed me and told me to meet her the next day and she would explain anyway it turned out her husband was watching us the whole time and he would fuck her straight after and he also had a thing about going down on her straight away my cock was bursting out my jeans by this time and I think that's my strangest sex story I went back several times lol as it really turned me on
I had an encounter at the end of a party at this guys large home and his girlfriend. Didn't know them but friend of a friend.

I was the last man standing and everyone had left. I was chatting to the host when his beautiful girlfriend took a liking to me running her fingers along my arm even while he spoke and watched on.

Before I knew what was happening she sat me down on the couch while he sat on the single seater opposite hilding a glass of whisky and proceeded to make out with me. I was so rock hard then she began massaging my cock through my pants before pulling me out and proceeded to give me an incredible handjob right in front of him while he sipped in silence.

Just before the wild finale he walked out seemingly unable to watched his lady finish me off. That was the most unusual one for me but also one of rhe most amazing encounters.
 
Here's another one...again at another large house party, meet this young sexy chick there and we got on pretty well, decided to look around house half drunk and found ehat appeared to be a office library.

She just half stripped off and sat down on the couch where I did only thing I wanted to at the time, I went down on her wanted to taste her pussy and gave her 2 orgasms. She just forced my head between her well spread thighs and gyrating hard....amazing
 
Two encounters definitely fit into the "strange" category...one awful and one wonderful. The awful first....

I met a woman online and we did some sexy chatting back and forth for only ten minutes or so. Very soon she invited me over to her place, saying that she wanted to give me a blowjob. She gave me her address and I headed over there...it was only 15 minutes away. I pulled up to a large apartment complex and found her unit. She greeted me and invited me in...there was literally no chit-chat, and she led me upstairs to her bedroom. First off, she was morbidly obese. I'm not hung up on body shape, but she was seriously immense. Oh well, I'm a nice guy, right? Why would I make someone feel unwanted because of this? So I just smiled and went with it. We went into her bedroom and she encouraged me to get completely naked, which I did. She started sucking my cock and I started moaning...she asked me to try to keep the noise down as her young daughter was asleep in the next room. 😬 How I stayed hard I have no idea, but she kept going and I tried to focus on feeling aroused so that I could finish and, honestly, get the hell out of there. It actually felt amazing, unlike anything I'd ever felt. I started thrusting my hips into her mouth and, while keeping quiet, let her know with my movements that she was doing an amazing job of getting me off. After enjoying what turned out to be an amazing blow job, I finally erupted in her mouth and she eagerly swallowed it all and spent a few minutes licking my softening cock. As I engaged in the polite after-talk that one has with a complete stranger who has just swallowed your cum, I watched in horror as she reached over to the nightstand, picking up her dentures and slipping them back into her mouth. 😲

I am ashamed to say that I pretty much just got the hell out of there. She later contacted me and wanted to suck me off again, and I politely declined. I did feel rather creeped out by the whole thing.
 
OK, the other strange one, this one with a far happier ending....

I corresponded with a married couple who wanted to have their first MMF. The husband wanted to suck his first cock, and the wife wanted to have her first new cock since being married. Everything clicked wonderfully during a couple of weeks of correspondence, and we arranged to meet in a local hotel. They got a suite in a very fancy local place, really nice. I met the husband in the cocktail lounge where we would chat; if it went well he would introduce me to his wife. Well, he and I hit it off nicely...he was just a very nice guy and easy to talk to. He explained that she was very nervous and was having a bath and a drink to relax. We enjoyed talking and, after about 30 minutes, he called his wife and told her that we were on our way up to the room. He led me up to the suite, which really impressed me...it was beautiful, with a roaring fire and candles burning everywhere. She had obviously put a lot of thought into making this a special evening for them.

She was in a beautiful, sheer robe, fresh from the bath. She was gorgeous, he was handsome, and I was a very happy man. We all felt very comfortable very quickly, and all settled onto the big king-sized bed. He and she kissed and fondled one another for a while while I watched, then she started undressing her husband. I took my clothes off and soon he and I were naked, she still in this sexy robe. It was their fantasy for him to suck his first cock, so I lay back as she started licking and sucking my cock while he watched very closely. After a while she encouraged him to join her, and soon both of them were licking my cock, taking turns sucking it. This was an amazing sight, and it was delightful that he was so excited and she was absolutely thrilled to watch her man doing this. After a while I was lying on my back, his wife kissing me and running her hands over my body while her husband got more and more into sucking my cock. For a first timer he was just fine. Ultimately he got the job done and, after I made sure that he was prepared, I blasted a huge load into his mouth. He worked very hard to swallow it all, and finished by cleaning my cock very nicely. She was positively squirming with excitement by now, and they kissed passionately for quite a while, her telling him how much it turned her on to watch him and how much she loved tasting my cum in his mouth. It was very, very hot.

Now it was her turn. I had no difficulty getting hard again and he lay across the bed as she and I began to make out. As I started running my hands up and down her body, the gown started to fall open and I was rewarded by a gorgeous body: small, firm tits with enormous, rock-hard nipples...I started eagerly licking and sucking and chewing on her amazing nipples and she went nuts. Soon she was writhing and moaning and telling me how fucking hot she was. I opened her robe further and exposed her beautiful pussy, completely smooth, with small labia and a very engorged clit. I started stroking it and noted floods of pussy juice from her eager sex. Now for my favorite thing in the world...I love worshipping a pussy with my mouth, and this pussy was simply stunning and clearly very aroused. It took no time at all for her to be grabbing my head and pressing my face into her crotch, cumming over and over with loud cries and moans...really one of the most erotic things I'd ever experienced.

And then, I perceived another moaning...a different moaning, not a good one. Her husband was curled into a fetal position on the bed, moaning and clutching his stomach. Everything came to an abrupt halt. He was experiencing some kind of acute abdominal pain, really severe and disabling pain, and naturally, she was concerned and was trying to ask him about it. He wasn't communicating very well, just mumbling a little bit, and she was stymied.

She was sexy as hell, clearly eager for my cock, but of course concerned about her husband's mysterious ailment. I went into ER nurse mode, expressing my concern for him and discussing our options. She obviously wanted to salvage the evening. I examined him, got his full history, discussed recent events, what he'd eaten, etc. It was obvious that he was suffering an anxiety attack. She and I talked for almost two hours, lying there naked in this beautiful room with her husband curled up at our feet. We talked about his condition, of course, but we went on to just talk about life and many things for the longest time.

Eventually he unwound. After about another hour of him now being included in our talking, we (somewhat miraculously) decided to re-commence our play. Honestly, I had been a bit conflicted...I'm a healthcare professional who is always concerned about helping people, and dear lord did I want to fuck this amazing woman! She obviously felt similarly, and so we had put enormous effort into keeping hope alive long into the night. It hadn't seemed possible a couple of hours previously, but we were damned determined. She and I ended up having amazing sex, and her husband just watched quietly. There had been rather instant chemistry between the two of us, and I think that it had freaked him out. Later, after we had been fucking for the longest time, she begged him to allow me to remove the condom. That was another head trip, watching the tortured look on his face as she pleaded with him to let her take my cum inside her. I couldn't let that go on...it was too painful to see him reacting to this and I didn't want him to have another panic attack. I instead suggested that we could compromise and, removing the condom, proceeded to lie on my back and have her ride me, grinding her pussy against my cock as she worked herself into an enormous orgasm, which triggered me to erupt all over my belly and chest. The evening finished on a hot note as she got her husband to join her licking it off my torso, frequently stopping to kiss one another, swapping cum with one another.

THAT was the strangest sexual encounter I've ever had, and one of the hottest, an odd combination. They were such nice folks, and so fucking sexy. By way of a "happy ending," so to speak, I received an email from them a week or two later, and they said that the experience had triggered days of discussions and were both eager to get together again.
 
OK, the other strange one, this one with a far happier ending....

I corresponded with a married couple who wanted to have their first MMF. The husband wanted to suck his first cock, and the wife wanted to have her first new cock since being married. Everything clicked wonderfully during a couple of weeks of correspondence, and we arranged to meet in a local hotel. They got a suite in a very fancy local place, really nice. I met the husband in the cocktail lounge where we would chat; if it went well he would introduce me to his wife. Well, he and I hit it off nicely...he was just a very nice guy and easy to talk to. He explained that she was very nervous and was having a bath and a drink to relax. We enjoyed talking and, after about 30 minutes, he called his wife and told her that we were on our way up to the room. He led me up to the suite, which really impressed me...it was beautiful, with a roaring fire and candles burning everywhere. She had obviously put a lot of thought into making this a special evening for them.

She was in a beautiful, sheer robe, fresh from the bath. She was gorgeous, he was handsome, and I was a very happy man. We all felt very comfortable very quickly, and all settled onto the big king-sized bed. He and she kissed and fondled one another for a while while I watched, then she started undressing her husband. I took my clothes off and soon he and I were naked, she still in this sexy robe. It was their fantasy for him to suck his first cock, so I lay back as she started licking and sucking my cock while he watched very closely. After a while she encouraged him to join her, and soon both of them were licking my cock, taking turns sucking it. This was an amazing sight, and it was delightful that he was so excited and she was absolutely thrilled to watch her man doing this. After a while I was lying on my back, his wife kissing me and running her hands over my body while her husband got more and more into sucking my cock. For a first timer he was just fine. Ultimately he got the job done and, after I made sure that he was prepared, I blasted a huge load into his mouth. He worked very hard to swallow it all, and finished by cleaning my cock very nicely. She was positively squirming with excitement by now, and they kissed passionately for quite a while, her telling him how much it turned her on to watch him and how much she loved tasting my cum in his mouth. It was very, very hot.

Now it was her turn. I had no difficulty getting hard again and he lay across the bed as she and I began to make out. As I started running my hands up and down her body, the gown started to fall open and I was rewarded by a gorgeous body: small, firm tits with enormous, rock-hard nipples...I started eagerly licking and sucking and chewing on her amazing nipples and she went nuts. Soon she was writhing and moaning and telling me how fucking hot she was. I opened her robe further and exposed her beautiful pussy, completely smooth, with small labia and a very engorged clit. I started stroking it and noted floods of pussy juice from her eager sex. Now for my favorite thing in the world...I love worshipping a pussy with my mouth, and this pussy was simply stunning and clearly very aroused. It took no time at all for her to be grabbing my head and pressing my face into her crotch, cumming over and over with loud cries and moans...really one of the most erotic things I'd ever experienced.

And then, I perceived another moaning...a different moaning, not a good one. Her husband was curled into a fetal position on the bed, moaning and clutching his stomach. Everything came to an abrupt halt. He was experiencing some kind of acute abdominal pain, really severe and disabling pain, and naturally, she was concerned and was trying to ask him about it. He wasn't communicating very well, just mumbling a little bit, and she was stymied.

She was sexy as hell, clearly eager for my cock, but of course concerned about her husband's mysterious ailment. I went into ER nurse mode, expressing my concern for him and discussing our options. She obviously wanted to salvage the evening. I examined him, got his full history, discussed recent events, what he'd eaten, etc. It was obvious that he was suffering an anxiety attack. She and I talked for almost two hours, lying there naked in this beautiful room with her husband curled up at our feet. We talked about his condition, of course, but we went on to just talk about life and many things for the longest time.

Eventually he unwound. After about another hour of him now being included in our talking, we (somewhat miraculously) decided to re-commence our play. Honestly, I had been a bit conflicted...I'm a healthcare professional who is always concerned about helping people, and dear lord did I want to fuck this amazing woman! She obviously felt similarly, and so we had put enormous effort into keeping hope alive long into the night. It hadn't seemed possible a couple of hours previously, but we were damned determined. She and I ended up having amazing sex, and her husband just watched quietly. There had been rather instant chemistry between the two of us, and I think that it had freaked him out. Later, after we had been fucking for the longest time, she begged him to allow me to remove the condom. That was another head trip, watching the tortured look on his face as she pleaded with him to let her take my cum inside her. I couldn't let that go on...it was too painful to see him reacting to this and I didn't want him to have another panic attack. I instead suggested that we could compromise and, removing the condom, proceeded to lie on my back and have her ride me, grinding her pussy against my cock as she worked herself into an enormous orgasm, which triggered me to erupt all over my belly and chest. The evening finished on a hot note as she got her husband to join her licking it off my torso, frequently stopping to kiss one another, swapping cum with one another.

THAT was the strangest sexual encounter I've ever had, and one of the hottest, an odd combination. They were such nice folks, and so fucking sexy. By way of a "happy ending," so to speak, I received an email from them a week or two later, and they said that the experience had triggered days of discussions and were both eager to get together again.
Damn. Strange for sure, but sounds like you struck gold with that couple!
 
OK, the other strange one, this one with a far happier ending....

I corresponded with a married couple who wanted to have their first MMF. The husband wanted to suck his first cock, and the wife wanted to have her first new cock since being married. Everything clicked wonderfully during a couple of weeks of correspondence, and we arranged to meet in a local hotel. They got a suite in a very fancy local place, really nice. I met the husband in the cocktail lounge where we would chat; if it went well he would introduce me to his wife. Well, he and I hit it off nicely...he was just a very nice guy and easy to talk to. He explained that she was very nervous and was having a bath and a drink to relax. We enjoyed talking and, after about 30 minutes, he called his wife and told her that we were on our way up to the room. He led me up to the suite, which really impressed me...it was beautiful, with a roaring fire and candles burning everywhere. She had obviously put a lot of thought into making this a special evening for them.

She was in a beautiful, sheer robe, fresh from the bath. She was gorgeous, he was handsome, and I was a very happy man. We all felt very comfortable very quickly, and all settled onto the big king-sized bed. He and she kissed and fondled one another for a while while I watched, then she started undressing her husband. I took my clothes off and soon he and I were naked, she still in this sexy robe. It was their fantasy for him to suck his first cock, so I lay back as she started licking and sucking my cock while he watched very closely. After a while she encouraged him to join her, and soon both of them were licking my cock, taking turns sucking it. This was an amazing sight, and it was delightful that he was so excited and she was absolutely thrilled to watch her man doing this. After a while I was lying on my back, his wife kissing me and running her hands over my body while her husband got more and more into sucking my cock. For a first timer he was just fine. Ultimately he got the job done and, after I made sure that he was prepared, I blasted a huge load into his mouth. He worked very hard to swallow it all, and finished by cleaning my cock very nicely. She was positively squirming with excitement by now, and they kissed passionately for quite a while, her telling him how much it turned her on to watch him and how much she loved tasting my cum in his mouth. It was very, very hot.

Now it was her turn. I had no difficulty getting hard again and he lay across the bed as she and I began to make out. As I started running my hands up and down her body, the gown started to fall open and I was rewarded by a gorgeous body: small, firm tits with enormous, rock-hard nipples...I started eagerly licking and sucking and chewing on her amazing nipples and she went nuts. Soon she was writhing and moaning and telling me how fucking hot she was. I opened her robe further and exposed her beautiful pussy, completely smooth, with small labia and a very engorged clit. I started stroking it and noted floods of pussy juice from her eager sex. Now for my favorite thing in the world...I love worshipping a pussy with my mouth, and this pussy was simply stunning and clearly very aroused. It took no time at all for her to be grabbing my head and pressing my face into her crotch, cumming over and over with loud cries and moans...really one of the most erotic things I'd ever experienced.

And then, I perceived another moaning...a different moaning, not a good one. Her husband was curled into a fetal position on the bed, moaning and clutching his stomach. Everything came to an abrupt halt. He was experiencing some kind of acute abdominal pain, really severe and disabling pain, and naturally, she was concerned and was trying to ask him about it. He wasn't communicating very well, just mumbling a little bit, and she was stymied.

She was sexy as hell, clearly eager for my cock, but of course concerned about her husband's mysterious ailment. I went into ER nurse mode, expressing my concern for him and discussing our options. She obviously wanted to salvage the evening. I examined him, got his full history, discussed recent events, what he'd eaten, etc. It was obvious that he was suffering an anxiety attack. She and I talked for almost two hours, lying there naked in this beautiful room with her husband curled up at our feet. We talked about his condition, of course, but we went on to just talk about life and many things for the longest time.

Eventually he unwound. After about another hour of him now being included in our talking, we (somewhat miraculously) decided to re-commence our play. Honestly, I had been a bit conflicted...I'm a healthcare professional who is always concerned about helping people, and dear lord did I want to fuck this amazing woman! She obviously felt similarly, and so we had put enormous effort into keeping hope alive long into the night. It hadn't seemed possible a couple of hours previously, but we were damned determined. She and I ended up having amazing sex, and her husband just watched quietly. There had been rather instant chemistry between the two of us, and I think that it had freaked him out. Later, after we had been fucking for the longest time, she begged him to allow me to remove the condom. That was another head trip, watching the tortured look on his face as she pleaded with him to let her take my cum inside her. I couldn't let that go on...it was too painful to see him reacting to this and I didn't want him to have another panic attack. I instead suggested that we could compromise and, removing the condom, proceeded to lie on my back and have her ride me, grinding her pussy against my cock as she worked herself into an enormous orgasm, which triggered me to erupt all over my belly and chest. The evening finished on a hot note as she got her husband to join her licking it off my torso, frequently stopping to kiss one another, swapping cum with one another.

THAT was the strangest sexual encounter I've ever had, and one of the hottest, an odd combination. They were such nice folks, and so fucking sexy. By way of a "happy ending," so to speak, I received an email from them a week or two later, and they said that the experience had triggered days of discussions and were both eager to get together again.
That was strange about him curling up while in a panic attack...that fear of regret and probably some jealousy maybe.

Thats probably what may have happened in my first example. He walked out before she finished me but what happened in between was sensational.

We made out like some teenage couple and I was honestly overwhelmed by the smell of her delicate perfume and the sexy stares from her glassy eyes. This wasn't something that happened all the time just lucky that night I guess. And seeing her beauty so close, biting her lower lip and softly moaning in excitement as she held my cock in her hand.

Right or wrong I teased her while staring back at him, like I am deliberately taunting him. She whispered naughty things back to me and I responded at least equally. It must have be torture for him. But I lived in the moment and this ain't going to be repeated and I am going show him how much pleasure it is being with her. She was amazing not just beautiful but she is his girl. When I finally told her to go.....he walked out just before she finished.

Probably sick in the stomach like your guy.
 
Last edited:
Being in a life long cuckold I have many strange or unusual sexual encounters. Well, truth be told most are the wife's encounters. One that comes to mind was during a cruise to Bermuda. The timing was in the middle of my committed Chastity arrangement. Upon arriving at one of our favorite vacation islands we promptly went to our favorite beach. Getting there early we chose our spot and made our place. My wife laid in the sun while I snorkeled. After a couple of hours I was tired and ready for a nap.
Settling in for a much needed nap, my wife kissed me and said she was going to the beach bar for a drink. I don't know how long I slept, but I was awoken with a kiss from my beautiful wife. She kissed me and said. Time to wake up honey. I need you to do something for me. What baby?. Come to the bar with me and thank the bar tender for fucking your wife so well. What? The handsome black bar tender wants to meet you. He just fucked me in a storage room in the back of the men's room and you need to thank him!.
We went to the bar where our seats had been kept empty. He greeting me with a huge smile and his hand out. People sitting at the bar watched and listened as I thanked him. My wife teels me you took very good care of her, I truly appreciate it. Look how happy and how she glows thanks to you. He handed me a Cuban cigar and the drink list. Well that was the beginning.
 
OK, the other strange one, this one with a far happier ending....

I corresponded with a married couple who wanted to have their first MMF. The husband wanted to suck his first cock, and the wife wanted to have her first new cock since being married. Everything clicked wonderfully during a couple of weeks of correspondence, and we arranged to meet in a local hotel. They got a suite in a very fancy local place, really nice. I met the husband in the cocktail lounge where we would chat; if it went well he would introduce me to his wife. Well, he and I hit it off nicely...he was just a very nice guy and easy to talk to. He explained that she was very nervous and was having a bath and a drink to relax. We enjoyed talking and, after about 30 minutes, he called his wife and told her that we were on our way up to the room. He led me up to the suite, which really impressed me...it was beautiful, with a roaring fire and candles burning everywhere. She had obviously put a lot of thought into making this a special evening for them.

She was in a beautiful, sheer robe, fresh from the bath. She was gorgeous, he was handsome, and I was a very happy man. We all felt very comfortable very quickly, and all settled onto the big king-sized bed. He and she kissed and fondled one another for a while while I watched, then she started undressing her husband. I took my clothes off and soon he and I were naked, she still in this sexy robe. It was their fantasy for him to suck his first cock, so I lay back as she started licking and sucking my cock while he watched very closely. After a while she encouraged him to join her, and soon both of them were licking my cock, taking turns sucking it. This was an amazing sight, and it was delightful that he was so excited and she was absolutely thrilled to watch her man doing this. After a while I was lying on my back, his wife kissing me and running her hands over my body while her husband got more and more into sucking my cock. For a first timer he was just fine. Ultimately he got the job done and, after I made sure that he was prepared, I blasted a huge load into his mouth. He worked very hard to swallow it all, and finished by cleaning my cock very nicely. She was positively squirming with excitement by now, and they kissed passionately for quite a while, her telling him how much it turned her on to watch him and how much she loved tasting my cum in his mouth. It was very, very hot.

Now it was her turn. I had no difficulty getting hard again and he lay across the bed as she and I began to make out. As I started running my hands up and down her body, the gown started to fall open and I was rewarded by a gorgeous body: small, firm tits with enormous, rock-hard nipples...I started eagerly licking and sucking and chewing on her amazing nipples and she went nuts. Soon she was writhing and moaning and telling me how fucking hot she was. I opened her robe further and exposed her beautiful pussy, completely smooth, with small labia and a very engorged clit. I started stroking it and noted floods of pussy juice from her eager sex. Now for my favorite thing in the world...I love worshipping a pussy with my mouth, and this pussy was simply stunning and clearly very aroused. It took no time at all for her to be grabbing my head and pressing my face into her crotch, cumming over and over with loud cries and moans...really one of the most erotic things I'd ever experienced.

And then, I perceived another moaning...a different moaning, not a good one. Her husband was curled into a fetal position on the bed, moaning and clutching his stomach. Everything came to an abrupt halt. He was experiencing some kind of acute abdominal pain, really severe and disabling pain, and naturally, she was concerned and was trying to ask him about it. He wasn't communicating very well, just mumbling a little bit, and she was stymied.

She was sexy as hell, clearly eager for my cock, but of course concerned about her husband's mysterious ailment. I went into ER nurse mode, expressing my concern for him and discussing our options. She obviously wanted to salvage the evening. I examined him, got his full history, discussed recent events, what he'd eaten, etc. It was obvious that he was suffering an anxiety attack. She and I talked for almost two hours, lying there naked in this beautiful room with her husband curled up at our feet. We talked about his condition, of course, but we went on to just talk about life and many things for the longest time.

Eventually he unwound. After about another hour of him now being included in our talking, we (somewhat miraculously) decided to re-commence our play. Honestly, I had been a bit conflicted...I'm a healthcare professional who is always concerned about helping people, and dear lord did I want to fuck this amazing woman! She obviously felt similarly, and so we had put enormous effort into keeping hope alive long into the night. It hadn't seemed possible a couple of hours previously, but we were damned determined. She and I ended up having amazing sex, and her husband just watched quietly. There had been rather instant chemistry between the two of us, and I think that it had freaked him out. Later, after we had been fucking for the longest time, she begged him to allow me to remove the condom. That was another head trip, watching the tortured look on his face as she pleaded with him to let her take my cum inside her. I couldn't let that go on...it was too painful to see him reacting to this and I didn't want him to have another panic attack. I instead suggested that we could compromise and, removing the condom, proceeded to lie on my back and have her ride me, grinding her pussy against my cock as she worked herself into an enormous orgasm, which triggered me to erupt all over my belly and chest. The evening finished on a hot note as she got her husband to join her licking it off my torso, frequently stopping to kiss one another, swapping cum with one another.

THAT was the strangest sexual encounter I've ever had, and one of the hottest, an odd combination. They were such nice folks, and so fucking sexy. By way of a "happy ending," so to speak, I received an email from them a week or two later, and they said that the experience had triggered days of discussions and were both eager to get together again.

Damn. Sounds like he got overwhelmed. Maybe they should have started on a smaller level like hand play. Nice to hear you were helpful and you all got through it.
 
Strangest situation…I met up with a Bi couple…they wanted me to prove I was Bi before we got into a Bi MMF…so they wanted me to meet them in a hotel parking lot after work, I pulled up next to their car and the husband got out and got into the passenger side of my car, and the wife came up to my window…the guy asked me to pull my pants down… while the wife pulled up her top showing her braless tits. The husband then proceeded to give me a blow job while I sucked on the nipples of his wife…the husband then sat back and pulled his pants down to show me his hard cock…I leaned over and started licking and sucking on his cock for a few minutes…he gently pushed me away and then proceeded to give me one of the best blow jobs id ever had…and his wife was egging him on…telling him how hot it was…to ‘suck the thick cock’…then she started kissing me and telling me to cum in his mouth…egging me on…so, I came into his mouth and he swallowed my load…then he leaned across me and kissed his wife, sharing some of my cum with her………we hooked up inside the same hotel the next week for my first Bi MMF
 
OK, the other strange one, this one with a far happier ending....

I corresponded with a married couple who wanted to have their first MMF. The husband wanted to suck his first cock, and the wife wanted to have her first new cock since being married. Everything clicked wonderfully during a couple of weeks of correspondence, and we arranged to meet in a local hotel. They got a suite in a very fancy local place, really nice. I met the husband in the cocktail lounge where we would chat; if it went well he would introduce me to his wife. Well, he and I hit it off nicely...he was just a very nice guy and easy to talk to. He explained that she was very nervous and was having a bath and a drink to relax. We enjoyed talking and, after about 30 minutes, he called his wife and told her that we were on our way up to the room. He led me up to the suite, which really impressed me...it was beautiful, with a roaring fire and candles burning everywhere. She had obviously put a lot of thought into making this a special evening for them.

She was in a beautiful, sheer robe, fresh from the bath. She was gorgeous, he was handsome, and I was a very happy man. We all felt very comfortable very quickly, and all settled onto the big king-sized bed. He and she kissed and fondled one another for a while while I watched, then she started undressing her husband. I took my clothes off and soon he and I were naked, she still in this sexy robe. It was their fantasy for him to suck his first cock, so I lay back as she started licking and sucking my cock while he watched very closely. After a while she encouraged him to join her, and soon both of them were licking my cock, taking turns sucking it. This was an amazing sight, and it was delightful that he was so excited and she was absolutely thrilled to watch her man doing this. After a while I was lying on my back, his wife kissing me and running her hands over my body while her husband got more and more into sucking my cock. For a first timer he was just fine. Ultimately he got the job done and, after I made sure that he was prepared, I blasted a huge load into his mouth. He worked very hard to swallow it all, and finished by cleaning my cock very nicely. She was positively squirming with excitement by now, and they kissed passionately for quite a while, her telling him how much it turned her on to watch him and how much she loved tasting my cum in his mouth. It was very, very hot.

Now it was her turn. I had no difficulty getting hard again and he lay across the bed as she and I began to make out. As I started running my hands up and down her body, the gown started to fall open and I was rewarded by a gorgeous body: small, firm tits with enormous, rock-hard nipples...I started eagerly licking and sucking and chewing on her amazing nipples and she went nuts. Soon she was writhing and moaning and telling me how fucking hot she was. I opened her robe further and exposed her beautiful pussy, completely smooth, with small labia and a very engorged clit. I started stroking it and noted floods of pussy juice from her eager sex. Now for my favorite thing in the world...I love worshipping a pussy with my mouth, and this pussy was simply stunning and clearly very aroused. It took no time at all for her to be grabbing my head and pressing my face into her crotch, cumming over and over with loud cries and moans...really one of the most erotic things I'd ever experienced.

And then, I perceived another moaning...a different moaning, not a good one. Her husband was curled into a fetal position on the bed, moaning and clutching his stomach. Everything came to an abrupt halt. He was experiencing some kind of acute abdominal pain, really severe and disabling pain, and naturally, she was concerned and was trying to ask him about it. He wasn't communicating very well, just mumbling a little bit, and she was stymied.

She was sexy as hell, clearly eager for my cock, but of course concerned about her husband's mysterious ailment. I went into ER nurse mode, expressing my concern for him and discussing our options. She obviously wanted to salvage the evening. I examined him, got his full history, discussed recent events, what he'd eaten, etc. It was obvious that he was suffering an anxiety attack. She and I talked for almost two hours, lying there naked in this beautiful room with her husband curled up at our feet. We talked about his condition, of course, but we went on to just talk about life and many things for the longest time.

Eventually he unwound. After about another hour of him now being included in our talking, we (somewhat miraculously) decided to re-commence our play. Honestly, I had been a bit conflicted...I'm a healthcare professional who is always concerned about helping people, and dear lord did I want to fuck this amazing woman! She obviously felt similarly, and so we had put enormous effort into keeping hope alive long into the night. It hadn't seemed possible a couple of hours previously, but we were damned determined. She and I ended up having amazing sex, and her husband just watched quietly. There had been rather instant chemistry between the two of us, and I think that it had freaked him out. Later, after we had been fucking for the longest time, she begged him to allow me to remove the condom. That was another head trip, watching the tortured look on his face as she pleaded with him to let her take my cum inside her. I couldn't let that go on...it was too painful to see him reacting to this and I didn't want him to have another panic attack. I instead suggested that we could compromise and, removing the condom, proceeded to lie on my back and have her ride me, grinding her pussy against my cock as she worked herself into an enormous orgasm, which triggered me to erupt all over my belly and chest. The evening finished on a hot note as she got her husband to join her licking it off my torso, frequently stopping to kiss one another, swapping cum with one another.

THAT was the strangest sexual encounter I've ever had, and one of the hottest, an odd combination. They were such nice folks, and so fucking sexy. By way of a "happy ending," so to speak, I received an email from them a week or two later, and they said that the experience had triggered days of discussions and were both eager to get together again.
Wow, that was a wonderful story and you sound like a wonderful guy. I hope the three of you got together soon after because I can't imagine anyone better at guiding them through their early MMF experiences.
 
Back
Top