Have you had sex with a friend of your wife before you were together? Does she know?

[danng]

Looking for stories similar to mine. Is there someone in you and your wife’s social circle (friends, family, coworkers, etc) that you slept with before you were together? Does she know? If so how does she feel about it?

My wife and I were in the same social group in high school and stayed friends with the same core group throughout our late teens/early 20s. We did hook up twice. Making out and hand stuff but never had sex. From her senior year until she was 22 she dated a good friend of mine. During that time she’d sometimes play “matchmaker” for me. Trying to set me up with girls she knew. So she is aware she was responsible for a lot of my sex life during that time. One thing she didn’t know when we finally started dating when we were both 25 is that I had slept with her best friend two times.

We’ll call her friend Tina. She is tall and slim, thick black hair, dark tan skin (she is of Easter European decent) with small B cup boobs but has nice thick thighs and a round, but not big, butt. We were all at a party when we were 20. Drinks were flowing and everyone was drunk. My wife was dating Pete at the time and they, along with the other couples in the group, had made their ways to bedrooms to fuck and/or pass out. A few of us remained awake including Tina. As the others dropped one by one I found myself finishing a bottle of tequila with Tina. We were chums but not close and I’d never thought of her sexually or romantically. The details are hazy but eventually we were in a home office room on the floor making out. This lasted a long time. Maybe an hour. I had her shirt off and was caressing her small tits and big erect nipples and her hand stroked my cock through my pants.

We were behind a large metal desk with moonlight filling the room. The alcohol started to wear off because the details thereafter are more vivid. I was suddenly super into Tina. She was very sexual and confident in our making out. I asked he if I could go down on her and she nodded. I undid the fly of her jeans and grabbed the waist of them along with her panties and peeled them down revealing her trimmed black bush and her large clit and pussy lips. Not freakishly large but bigger than average. I sucked her nipples and ran my fingers up her slit which was dripping wet. I kissed down her flat stomach until I reached her crotch. Going down on a woman has always been my favorite part of sex. And by 20 I had done it enough to know what I was doing. I started to flick my tongue up her slit tasting her juices. Then moved to her clit. Her hands were gripping my shoulders and running through my hair and she moaned. She got louder and louder until she let out a muffled “holy fuck!” And came.

She sat back breathing heavy. Sweat glistened in her small titties in the moonlight. She sat up and pushed me down and pulled down my shorts. She stroked my cock and gave me the kinkiest dirtiest smirk looking into my eyes. She took me all the way into her throat. Cupping my balls and sucking me. After a minute or so I tapped her shoulder and said I was going to cum. And she said go ahead. She sat back and stroked me hard as I spurted my load onto myself.

We both laid back and gave each other a few “wow” comments. I said I’d have lasted longer without her stroking my cock for the last hour. She said that was the best orgasm she’d ever had and my ego was in the clouds. After a half hour or so the making out started up again and I was back between her legs within a few minutes. I made her cum again with my mouth then she rested again. She looked down at my dick and said “I need that in me” and pushed me back again. She swung a leg over me and grabbed the base of my dick, working the tip up and down her wet pussy lips. Then she slowly sat down. I felt her pussy engulf my entire dick one inch at a time. As she hit the bottom she let out a small “mmmm”. She rocked her hips back and forth rubbing her clit on me and her legs buckled and I felt her cumming on me. She then placed her feet on the floor and slid up my shaft bouncing up and down on my cock. I’d never been fucked like that before. I was close to cumming again but didn’t want to yet so I took her off of me and turned her over. She was on her knees and positioned her ass way up in the air. Her pussy and ass spread apart looks so good. I took a few licks from behind and then slid my dick inside her. I fucked her hard and she reached back pulling my body into her. I gripped both of her ass cheeks then after a minute or so I pulled out as I came. She quickly turned around and jerked me off onto her.

The sun was just coming up and we got cleaned up and we went home. The next day I felt awkward. It was the best sex I’d ever had but I still had no desire to date Tina. I hoped she felt the same. I gave her a call and said it was quite the night. Before I could even broach the subject she said “we’re still friends right?” And I said “yeah. I’m not looking for anything serious right now”.

This got long so I’ll pause and finish later. The other time I fucked Tina and how it finally came up to my wife.

[jellyworm]

Please do tell us about the second time you fucked Tina. Great story! We want more!!

[danng]

Several months later we were all partying again. We had a bonfire at a friends house. I showed up late because I had been at work. Everyone was already wasted and I was tired so after a few beers I decided to head home while I could still drive. Tina approached me and asked for a ride home. She said she wasn’t feeling the party that night either a few minutes down the road she suggested we get some drinks and hang out at my place. This wasn’t out of the ordinary. We were friends and had barely mentioned the night we hooked up since it had happened. So i got a six pack and she got some wine and back at my apartment we put on some music and chatted and drank.

As the booze started to hit us we got a little flirty. She was wearing a pair of white jean shorts that showed off her sexy tan thighs. And a black tank top with no bra. I mentioned at one point her nipples were poking and I could tell she had no bra. She laughed and said she barely wore one because she has no tits. I told her they were good by me and she blushed.

Eventually she ended up next to me on the couch and we kissed. I had my hands going through her thick hair and her hands started to wander. I was feeling her tits through her shirt while she stroked my hard on through my pants. I was just about to pay her back to eat her out but she got down to the floor first. She slid my pants down and pulled them off. Then she took off her shirt. Her dark nipples pointing out. Then she did the sexiest thing I think a woman can do: she tied her hair back in preparation to blow me. The lamps were on so I could see her better this time. She really was sexy. One of those girls that’s not exactly pretty but sexy if that makes sense.

She was less sloppy and more methodical about it this time. She licked my cock from base to tip slowly. Gripping my cock and taking the first couple inches into her mouth. Then working up to taking the whole thing. She sucked me this way, going from near the top to sliding her moth all the way to the base. Slowly at first. Then faster. After a few minutes I could feel I was going to cum. I tapped her on the shoulder to let her know and she just kept sucking me. Now she placed her lips around the head and stroked by shaft with her hand. I gripped her shoulders as I orgasmed and shot my load into her mouth. She swallowed each spurt and kept stroking me slowly. When I was done she licked my cock base to tip then gave one last suck at the end getting the last of my cum.

She looked so sexy and proud of herself. She was incredible. I immediately returned the favor laying her on the couch. I removed her shorts and played with her pussy through her turquoise thong while sucking her nipples. I could feel how wet she was through the panties. I got to my knees and slid them off. She was fully shaved this time. I kissed her on her thick smooth thighs. Starting at one knee then working to the other. Then finally ending up in the middle. I licked her pussy from the bottom to the clit slowly. For maybe a minute when she grabbed my hair and positioned my head at her clit. It was so hot how into it she was. I went to work on her clit and slid my first two fingers inside her. Flicking my tongue while fucking her with my fingers. She moaned and squeaked. Much more animated this time not worried about others hearing. She came a few times and eventually made me back off. She was so sensitive after multiple orgasms. We laid there naked fora but. Catching our breath and exchanging glances.

She asked if I wanted a drink and I said sure. I watched her round ass jiggle it’s way across the room and then her sexy body as she worked her way back. She sat with her legs over me and we chatted. After ten minute or so I felt myself getting hard again. I ran my hand up her leg and felt her pussy lips. She immediately put her drink down and straddled me. We made out with her running her wet pussy on my cock. Then she slid me into her and rocked back and forth and came on me. I laid her back and fucked her missionary. It was very passionate with lots of kissing. After several minutes I felt my load coming on and I pulled out and she stroked my cock until I came on her stomach.

We slept together naked and when I got up in the morning she was gone.

I’ll finish later.

[danng]

Not much else to tell here. Tina and I never fucked again but we made comments about it a few times. When I started dating my wife we got serious pretty quick. After a few months we had the sexual past conversation and she said she knew most of my sexual encounters so I didn’t have much to say. I said there’s a couple she may not know about and I told her of them but when I got to Tina she asked for a lot of detail. I could sense a bit of jealousy and maybe annoyance that Tina never told her. We both have a past and don’t really have an issue with it and my wife doesn’t seem to mind when Tina is around if I talk to her or whatever. She’s made jokes about having a threesome with her some day. Only jokes but a guy can dream.

Anyone have any stories about having to reveal to their partner that they slept with someone they are close with?

[SixPointFive]

Not sex, but one of my wife’s best friends jerked me off outside a nightclub…

I first met my wife in 2000. We worked together as she had a summer job before finishing uni. We flirted a bit, went out a couple of times but I wasn’t interested in the whole relationship thing.

Fast forward 3 years and she’s engaged and living with her fiancé. We’re still in regular, semi-flirty touch and when I had a work night out in the City Centre that coincided with her and her friends being out, we agreed to meet up.

Abandoning my dull work colleagues, I met her and 3 of her fellow teachers at a City Centre bar, moving onto a club as we approached midnight.

One of her friends, Helen was a quiet, pretty girl who also with her fiancé just outside of town.

Helen was flirty and drunk. I was….well the usual me who, after 3 years single was fully into the “shag anyone” approach. As the night wore on it was just me, Helen and my future wife left. We danced, we drank, we flirted. When it was just me and Helen on the dance floor I made my moved and we spent a few mins kissing with the usual arse grabbing/grinding.

Outside the club, as we waiting for a taxi my future missus disappeared to get some money for the ride home, Helen gave me a drunken hand job in the back alley.

We all jumped in the taxi back to Helen’s where her fiancé was surprised to see me (especially as he knew Rach’a fiancé as they did a lot as a foursome) but I waved off his worries by saying I was “just a friend” and obviously he knew nothing of the fact his wife to be had just jerked me off.

So, fast forward 12 months. Helen & Andy are getting married, Rach and I are now an item after she and I both saw sense. Rach knows all about the hand job and refers to it regularly- half in jest, half in mild annoyance/jealousy.

Helen knows. I know. Rach knows. Andy knows nothing.

We are at their wedding, Helen is super nervous around me. The one time in her life she touches a dick that isn’t Andy’s and instead of never seeing me again, here I am part of their lives for every more.

So, fast forward another 15 years. Rach and Helen no longer work together but are still great friends. We occasionally meet as a foursome, or with our kids in tow for family activities. Rach is still always a bit jumpy round me, Andy still oblivious. My wife eyes me suspiciously if I ever get flirty with Helen….

Who knows, I might ask her for an encore one of these days

[Massguy70]

I can't think of any that I slept with before we got together but for one ex, I hooked up with two of her friends and two relatives after we broke up.

[whatnow3]

Probably just not exactly a match for this thread but the only friend of my wife I have slept with is actually my ex girlfriend from school, Stacie, who I’ve written some stories about. Because Stacie and I remained friends after we broke up, and had the same group of friends we always hung out with, once I started dating Lisa she got to know Stacie and they are now friends. And Lisa is aware, even knowing that before she and I became exclusive, Stacie and I had a fwb thing going on.

[1michael]

My wife had lots of GF's that she hung out with and one that comes to my mind first is her GF that lived across the street from her house! At the time I didn't know my wife and where she lived, but the girl across the street worked as a Barmaid in my buddy's BAR and I went out with many of his female employees~
I found out later that all of these girls would talk about the guys, just like the guys talk about the girls! So I knew later on that my wife knew that I enjoyed her GF across the street for a nice long time! They still keep in touch today and meet for meals and gossip too!
It was at our Wedding that I got to meet the rest of my wife's family. That's were I ran into a girl that I took out and she spent plenty of nights at my place too! Being with my wife I found out that she is a cousin to my wife and I never knew that till this moment when I asked what was she doing at our Wedding?
My wife did make her normal get to the point statement, "So you got screwed by him too!". There was a silent moment as well as a somber look on her face and mine, then we all just chuckled over it!
Its funny how things come around and you find out stuff by accident~


Nice to see just how many of these Threads here brings back those Memories!

[DJS1985]

Not a friend of hers, but instead a cousin of hers before we were together. I didn’t know that it was her cousin until after we got together, neither one of us never said anything about it to her. Her cousin was married to a guy that was a total jerk to her, so me and her ended up clicking then fucking a few times when her husband wasn’t around. I met my then wife a year later after the last time me and her cousin fucked. I didn’t even know the two were cousins until after we was engaged. All the above happened before meeting my first wife, it all was a long time ago.

[Naddy3]

No, but several AFTER.