Unexpected sex

[wifeswolf]

Have any of you had sex with someone you never expected to hook up with? Maybe someone with a large age gap or that you though was out of your league, or simply was unattainable for any number of reasons. Tell of your encounter here.

 

[gtnlynn]

When my wife was 39, we agreed that she could have sex with others, limited to one "date" with each man. She had a few dates with younger men in their 20s who called on the medical office where she worked. She never expected to have sex with the 65 year old doctor from another country who sometimes used their office to see patients. He asked her to be his escort to a big event, and she agreed. They ended up having great sex in his big penthouse apartment.

 

[wifeswolf]

I had it happen twice.
First time, I went back to my hometown for a friend's wedding. Both he and his bride were HS sweethearts and her sister was a year ahead of us in HS. The sister was the cheerleader with the hot body that every guy wanted to date but most of us were too shy to even ask. There was a rumor going around that she was dating a guy in college, so even more likely unattainable.
At the reception, she actually approached me and started to chat. She seamed quite friendly. More so that she ever was when in HS. The bride and groom left for their honeymoon, the reception was winding down and she invited me and a few other people over to her house to continue the party.
We drank and played the staple of 80s games "Twister" and a bit of truth or dare and people started to leave. I was one of the last guests. The warm day had turned to a cold Ohio night and as I put my shoes on I muttered, "Damn, I don't want to go to that hotel." Mainly hating the idea of going out into the cold. As I was heading to the door, she grabbed my arm and pulled me back, "You don't have to go." she said. I stood in silence as she ushered the last guests out, then closed the door, turned and kissed me. It was passionate and lustful and lasted for what felt like an hour. We shed our clothes without words as we headed to the bedroom. The first time any one spoke was when I was naked and realizing I was not prepared and said, "I don't have protection." She said "You don't need it." and pulled me in the bed on top of her. The rest doesn't need description you all can imagine what 2 20somethings did. We tried a log distance romance, but you know how those thing go. But damn it was fun while it lasted.

Second time, was over 3 decades later. Raised 3 kids and wife and I were ready to explore our new freedom. Had a neighbor that we were very friendly with a divorced woman living alone that was over 10 years older than my wife. After inviting her to dinner, we enjoyed conversation and drinks ( Now too old for twister) and somehow the conversation turned to sex. When the topic of fantasies turned up I got nervous and thought that my wife would reveal that we had tried a 3some and a 4some, but she shocked me more when she blurted out, "I wanna make a woman cum...and I want to know what it feels like to get an orgasm by a woman. " (We talked about being honest with each other, but freeking hell.) The neighbor took it in stride and said "honey, let me show you. I know all the best spots. " She stood and reached for my wife's hand. My wife stood and they walked to the bedroom, our neighbor glancing back at me with a smile. One of the most erotic nights of my life. I didn't get to touch the neighbor, so by definition it wasn't having sex, but that night I didn't care. A couple of years later we moved out of state. Again it was fun while it lasted.

 

[wifeswolf]

When my wife was 39, we agreed that she could have sex with others, limited to one "date" with each man. She had a few dates with younger men in their 20s who called on the medical office where she worked. She never expected to have sex with the 65 year old doctor from another country who sometimes used their office to see patients. He asked her to be his escort to a big event, and she agreed. They ended up having great sex in his big penthouse apartment.

I like the occasional younger/ older sex. My wife has had men from 18 to 82 and I enjoyed women from 36 to 70....though in less numbers.

 

[gtnlynn]

I like the occasional younger/ older sex. My wife has had men from 18 to 82 and I enjoyed women from 36 to 70....though in less numbers.

Sounds like a good arrangement.

 

[mustang_driver]

She was a friend in college. We worked together, partied together, hung out and listened to music together, but I was not attracted to her at all and I didn't know she was attracted to me. One afternoon during the summer, we were hanging out at her place drinking and listening to music. We were sitting on the cement of her patio when I feel her hand slide up the back of my shorts leg. I was a bit stunned and didn't know what to do, but being drunk at the time I didn't stop her either. Her hand continued up my leg and eventually found it's way inside the leg of my boxers and to my cock. I quickly became hard and she proceeded to stroke me. It felt so good that I let he continue. After a bit, we moved inside and she proceeded to jump me, kissing me hard. She quickly pulled off my shorts and proceeded to devour my cock with one of the best blowjobs I've ever had. When I got really close to cumming, I pulled out of her mouth and flipped her on her back. I roughly pushed her shirt and bra up and began sucking on her nipples. Then I yanked off her shorts, climbed on top and fucked her furiously until I came. Nothing ever happened again after that, but it did change our friendship a bit as we stopped hanging out together without anyone else there..

 

[wifeswolf]

She was a friend in college. We worked together, partied together, hung out and listened to music together, but I was not attracted to her at all and I didn't know she was attracted to me. One afternoon during the summer, we were hanging out at her place drinking and listening to music. We were sitting on the cement of her patio when I feel her hand slide up the back of my shorts leg. I was a bit stunned and didn't know what to do, but being drunk at the time I didn't stop her either. Her hand continued up my leg and eventually found it's way inside the leg of my boxers and to my cock. I quickly became hard and she proceeded to stroke me. It felt so good that I let he continue. After a bit, we moved inside and she proceeded to jump me, kissing me hard. She quickly pulled off my shorts and proceeded to devour my cock with one of the best blowjobs I've ever had. When I got really close to cumming, I pulled out of her mouth and flipped her on her back. I roughly pushed her shirt and bra up and began sucking on her nipples. Then I yanked off her shorts, climbed on top and fucked her furiously until I came. Nothing ever happened again after that, but it did change our friendship a bit as we stopped hanging out together without anyone else there..

Ah yes...the NSTBA (not safe to be alone) relationship.

 

[Horny2019]

I’ve had one experience like this. I was in high school. My sister had a good friend, they were both a year behind me in school. I knew my sisters friend but never really ran around with them, just casual crossing at school. One day my sisters friend asked me to come to help her with something, now 40 years later I don’t remember what the reason was but I showed up at her friends house. She was home alone and was soon coming on to me. Soon my cock was buried in her pussy and we were having a good time. We never hooked up again but it was a good time.

 

[Isinlarsa]

A friend of mine invited me to her wedding. Her bridesmatron had come in from out of town. She and I started talking at the reception, and before I knew it she was following me back to my apartment. Within less than two hours of meeting her I was fucking her.

 

[Lori_Lux]

My first time was unexpected. I was 18 and had an older friend. I was wearing panties secretly then and he found out.

I was always a bit femme and soft so I didn't really have friends with the other guys. My one neighbor was 26 and we would play video games. I visited often. One time I went in my sister's panties and he noticed somehow and got visibly hard in his gym shorts he always wore.

He asked if I wanted to suck him and I said yes. He had a big 8" cock and I really struggled with it, but he was very encouraging. He took me to his bedroom and bent me over. He pulled my panties down and pressed hard into me. It hurt bad for quite a while until I just sort of opened up and he began fucking me hard. I remember him behind over me and whispering in my ear "you're a total bottom bitch" and he blew inside me

 

[Njbody67]

Have any of you had sex with someone you never expected to hook up with? Maybe someone with a large age gap or that you though was out of your league, or simply was unattainable for any number of reasons. Tell of your encounter here.

I fucked my friends mother when I was around 20/21 and she was mid 40's. Phenomenal.

 

[vandelayatx]

I fucked my friends mother when I was around 20/21 and she was mid 40's. Phenomenal.

love this

 

[Njbody67]

love this

Even better, she essentially seduced me and it was crazy hot.

 

[jsilvers]

When I was in college, I had met a woman who was also going to school there. She was about 6 years younger than me (I was 25). We started dating casually and the sex was amazing. But that's not the unexpected sex.

I was out one night and this older (and very attractive) woman started flirting with me. I think she was 44 at the time. She said she had seen me out before with another woman and so she hadn't ever came up to talk with me. But since I was out alone that night, she came up and started to flirt.

After a few martinis, she kept hinting at coming home with me. The other woman and I were just dating casually. We both agreed that things weren't exclusive. So I invited this older woman home. We got back to my place and she came on strong. We ended up fucking three times that night.

The next morning, she asked me if I was going to change the sheets before I brought my young girlfriend into my bed again. I told her that I hadn't changed them before I brought her to bed with me, so I wasn't going to change them before the next woman came over.

We saw each other a few more times after that.

 

[Scotchlander]

Yes. A mates much younger wife.

She was out of work and I suggested she could do some cleaning for me and I would reward her.

After a few visits she started being flirty and was wearing very revealing clothing. She caught me looking one day and asked if I liked what I saw. I was red faced, but I admitted I did. So she came over to where I was sitting and told me to have a better look and raised her skirt so I could see her thong. She then said I could have a feel if I wanted to no guy could have resisted.

She still visits and unbeknown to her husband, we always fit in a good sex session.

 

[Isinlarsa]

When I was in college, I had met a woman who was also going to school there. She was about 6 years younger than me (I was 25). We started dating casually and the sex was amazing. But that's not the unexpected sex.

I was out one night and this older (and very attractive) woman started flirting with me. I think she was 44 at the time. She said she had seen me out before with another woman and so she hadn't ever came up to talk with me. But since I was out alone that night, she came up and started to flirt.

After a few martinis, she kept hinting at coming home with me. The other woman and I were just dating casually. We both agreed that things weren't exclusive. So I invited this older woman home. We got back to my place and she came on strong. We ended up fucking three times that night.

The next morning, she asked me if I was going to change the sheets before I brought my young girlfriend into my bed again. I told her that I hadn't changed them before I brought her to bed with me, so I wasn't going to change them before the next woman came over.

We saw each other a few more times after that.

Sounds like the older woman thought it would be hot for you to fuck your girlfriend on the same sheets where you fucked her. What was her reaction when you told her you had fucked her on the same sheets where you fucked your girlfriend?

If you and your girlfriend agreed you weren't exclusive, did she ever share with her times with other men?

 

[soflabbwlvr]

When I was in college I worked all four years at a research facility that was entirely composed of full professors and Ph.D. candidates, with a few undergraduates doing the lesser jobs. I was one of those undergraduates. All of my supervisors were women. I remember when I interviewed for the job, I was asked if I would have a problem working with a woman for a boss? I thought it was a ridiculous question, but answered it appropriately and got the job.
Anyway, the head of the project was a very attractive professor in her mid 30s. Below her was my immediate supervisor, who was a grad student in her early 30s. I did not consider her very attractive. She was OK looking, but she had a bent nose that detracted from her appearance. Her figure was OK, what could be seen of it under the baggy flannel shirts and oversized sweaters she always wore. But she was friendly and brilliant. I enjoyed working for her. We worked very closely, but she had a boyfriend and I had a girlfriend, so there was never any thought of it going anywhere.
Well, our department socialized together frequently, and during my last summer there we had a picnic at a local lake. I had broken up with my girlfriend 6 months earlier, and she had recently broken up with her boyfriend. Everyone was in bathing suits. "Jane" arrived a little late, and when she took off her cover up she revealed a stunning body in a small red bikini. I was shocked. I had no idea she looked that good under all her clothes. To this day I can still see her getting out of the lake, her body dripping with cold lake water and her nipples straining against the red triangles holding back those large breasts. Anyway, after that I paid much more attention to her in my final weeks at that job.
In mid August of that summer I had to leave for grad school in another state. As it turned out, Jane was leaving also, to complete her Ph.D at another school. I took a chance and invited her over to my place for dinner during our last week in town. She accepted, and came over that Friday evening. All my housemates were gone for the evening. I made dinner for the two of us, we smoked some weed and drank a few beers with dinner, then I put on some music and we started dancing in the living room. It was awkward, and before the first song was finished she asked me to show her my room. We went upstairs, kissed and the clothes came off. It was a night I will never forget. My first time with an older woman, and my first time with a woman I never thought I could get into bed. She wasn't beautiful, but her figure was perfect, she was sweet, and super intelligent. We spent that night together, and then on Monday they had a good bye party for us at work. She left the next day and I never saw her again.

 

[AZsurfer45]

Had a coworker from my college job decide to come up for a quick cabin trip with my guys. She was totally in the friend zone as she had dated my friend for years though they recently broke up. Not a stunner, very average appearance but she was fun to be around. Laid back. Easy going.

Drank a bit, night came. Buddies slept in the bunk house and I decided I’d sleep in her room with two small twins so she wouldn’t be alone in the main house at night.

Talked a bit but got to be sleepy time as we laid down. She went to go pee and I jumped in her bed in the dark as a prank. She was surprised to find me there and laughed as she laid on me. Then we made out and soon we’re naked and having full on sex.

Never had any attraction to her prior but we hooked up a few times after. She was a good lay.

 

[Horacefeely]

5th year HS reunion. The girl I had a huge crush on but was out of my league, and my eventual gf's friend.

She was at the check in table, and she immediately gave me a big hug. Didn't think much about that, old friends you know, but later she invited me to an after party. Just a few of the old gang, did not think that was significant either.

Now, she was always a hottie, dated guys older than her, but she was single at the party, as was I. We were there for about 15 minutes before she told me she always wanted to find out if what her friend, my HS gf, had told her about me.

She led me to a basement room and we finally both got what we had wanted years before.

I will be attending the 50th in a couple of months... I wonder what she is up to now.

 

[cubbies4vrs]

5th year HS reunion. The girl I had a huge crush on but was out of my league, and my eventual gf's friend.

She was at the check in table, and she immediately gave me a big hug. Didn't think much about that, old friends you know, but later she invited me to an after party. Just a few of the old gang, did not think that was significant either.

Now, she was always a hottie, dated guys older than her, but she was single at the party, as was I. We were there for about 15 minutes before she told me she always wanted to find out if what her friend, my HS gf, had told her about me.

She led me to a basement room and we finally both got what we had wanted years before.

I will be attending the 50th in a couple of months... I wonder what she is up to now.

Doggy style.

 

[imustadmit]

I worked with this young woman (early 20's) who was having car trouble and needed a ride home. It wasn't really convenient for me but I said sure. She'd always struck me as sorta sexy, but in a "I like my women on the trashy side" kinda way. I'd never really thought about hitting on her.

On the way, she tells me one of the other guys we work with had given her a ride a couple days prior, and had asked her for a blowjob once he took her home. she told me she obliged him. I was like "well shit! I bet we can do better than that!" She acted all coy, but I knew she was just a slut who was enjoying male attention.

I pulled off down a dirt road and found a spot. We kissed a little and before long I had my cock out and she was sucking it. I had my hand on top of her head as she bobbed up and down on my very suprised cock. I didn't wanna cum from the bj so I pulled her off and told her let's get out.

We were in the woods but she was still afraid of being caught. I told her I'd used this road before as a hookup spot and it was safe, which was a total lie....I didn't even know quite where we were! We got out and I led her to the back of the car where I took her clothes off and kissed her deeply. I sank to my knees and eat and fingered her pussy. I gave her 2 orgasms from my mouth and fingers.

Then I bent her over the back of the car and started fucking her doggystyle, slapping her tits from behind while I pounded her. She was loving this and so was I! I'd like to say I pounded her for 45 minutes but truth is I only lasted about 5 minutes, but it was 5 glorious minutes and we both did cum from the pounding.

 

[jsilvers]

Sounds like the older woman thought it would be hot for you to fuck your girlfriend on the same sheets where you fucked her. What was her reaction when you told her you had fucked her on the same sheets where you fucked your girlfriend?

If you and your girlfriend agreed you weren't exclusive, did she ever share with her times with other men?

The older woman said something like "yeah, I could tell you hadn't made the bed in a while" after I told her. She was acting rather coy about it. Honestly, if I had been maybe 10 years older, I would have totally been trying to get with her. She was super hot, had a great job, and was into a lot of things that I enjoyed. But she had a whole set of life stuff going on (I think she was recently divorced, or still in the process of it) and there was about 20 years age difference between us.

Me and the younger girl never spoke about any other dates. When we started seeing each other she had said, "I'm not looking for a serious boyfriend and I can be really jealous, so let's not talk about what we each get up to when we're not together". She was honest, which I give her credit for. But yeah, I never heard any stories about her with other men. Or women.

 

[HornyLittleDevil2026]

I had unexpected sex about 7 times if I remember correctly.
1. When I lost my virginity
2. To a coworker at a party
3. & 4. Girls I met at clubs back to back (something that never happened before or since)
5. One night stand/first date with girl I met on a dating site
6. Daughter of a coworker
7. Acquaintance I bumped into at a wedding

 

[bscurious922]

Hoping for some this Friday! An old co worker and I are meeting for lunch. Always have been very good friends, but she is going thru a divorce.

 

[HornyLittleDevil2026]

Hoping for some this Friday! An old co worker and I are meeting for lunch. Always have been very good friends, but she is going thru a divorce.

Good luck, and keep us posted!