Watching My Best Friend Fill My Wife

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What’s your gender? Male
How old are you? 53
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

Watching my best friend fill my wife

How long ago did this hookup happen? 3 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Dan had been a friend since we were both in second grade together. He was best man at our wedding and remained single so he was over at our house often and a part of our lives. Dan and I are both 53 years old and both attend the gym everyday together. He is 5’10 and weighs about 190 pounds with a muscular build and had more gray than I do. Dan and I are best friends and he is a good dependable friend to my wife.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was no planning to this. We had all been hanging out together that Saturday which is not abnormal for us. Dan and I had been to the gym and then when we returned home my wife said she wanted to go out for dinner. Dan did not have any plans and we all three went out.

When we returned home we decided to spend the evening in our backyard above ground pool since it was a warm September evening and I had not taken the pool down for the season. My wife made a pitcher of margaritas for her and Dan while I drank beer. Dan and I were in swim trunks and my wife was wearing a white bikini that looked great on her. She also works out daily and is in fantastic shape. Seeing her in a bikini was nothing new and outside of some joking and teasing there was never any sexual energy between my wife and Dan.

The margarita’s were strong with a recipe my wife found on Pinterest which had a 12 ounce can of each: Limeade, Fresca, Tequila and a can of Bourbon.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We had all been out of the pool for three or more hours and had dried off completely when we went inside at around midnight. I had drank about five beers and Dan and my wife had drank two full pitchers of the margarita concoction and were both acting silly and it was apparent they were both fairly drunk but having a good time.

I had got up to use the bathroom and when I returned to the living room Dan had moved from the recliner to sitting next to my wife on the couch where I had been. I grabbed a beer and sat in the recliner as we all laughed and talked. The TV had changed from an old action adventure to a rerun of the Bedtime Stories show from Cinemax After Dark. As the TV became a focal point instead of background noise I could see a difference in the looks between my wife and Dan. I could also see that Dan was doing his best to position himself to conceal that he had a huge boner happening.

Dan broke the silence as he turned from the TV to my wife and said “I have always been incredibly turned-on and aroused by you.” Without pausing my wife looked away from the TV and at Dan saying “I have always thought you were hot and I love seeing you with a hard-on when you’r around me.” I thought they were going to kiss but Dan got up and went into the restroom. I was shocked when my wife asked me “Is it alright if I give Dan and kiss?” I was not sure how to answer this and she followed up saying “Please!” I told her ok and Dan poked his head into the room and asked if I could help in make a drink in the kitchen. Once in the kitchen Dan apologized and asked if I wanted him to get an Uber and go home. I told him no, to stay and he said he was feeling pretty drunk and may end up doing something he would regret. I told him he was fine and that I was sort of aroused at seeing my wife the way she was acting. We walked back into the living room and Dan took his place back next to my wife and I sat on the other side of her on the couch.

It only took a moment or two and my wife leaned over and planted a huge kiss on Dan. Dan was obviously liking what had happened and my wife climbed up on top of his lap facing him and began to kiss him again this time very passionately. Dan looked at me once the kiss ended and said “I may not be able to stop if we go any further” and before he got that out my wife’s bikini top was off and she was sitting topless on my best friends lap grinding her pelvis into his erection. My own cock was now rock hard seeing my wife with her nipples rock hard as she got up and pulled my best friends shorts off him allowing his big cock to spring free. Dan was about 2″ bigger than I am and his cock had always been fat around. I watched as my wife knelt on the floor between his legs and sucked him into her hungry mouth.

After about ten minutes of watching my wife blow my best friend my wife sat back on Dan’s lap and was saying “fuck me Dan, I need to feel you inside me. I want you to fuck me.” she continued to bed him to fuck her and Dan grabbed her and stood up turning around and carrying her into our bedroom and laying her on her back in the middle of our mattress as his thumbs pushed inside the waist of her bikini bottom and he pulled them off her in one motion. My wife spread her legs and raised her knees still telling him to fuck her and Dan knelt between her legs and began pushing his large cock inside my wife’s wet pussy with her groaning and telling him not to stop. As Dan fucked my wife she was now saying “ow my god that feels so good, of god that is so big” It took Dan close to 10 minutes of pounding and hard fuckiing before I knew he was cumming and my wife was hollering “don’t stop, don’t pull out.” I watched my wife’s pussy filled with my best friend’s huge load of cum and as he went limp watched as cum leaked down between her cheeks.

I had just stood at the side of our bed watching my wife getting fucked hard and climaxing while being filled with my best friends cock and it was incredibly hot.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Dan had fallen asleep next to my wife as they both lay together in the orgasmic bliss of their afterglow. It was a few hours later when Dan got up and walked out into the living room where I was sitting still hard and contemplating what had just occurred. I was still drinking beer and Dan asked if I was ok. I replied yes and he asked if I was pissed. I told him no and we talked about what had happened. Dan was still naked and his cock was limp but I could see dried cum on his cock and balls and the thought of him being inside my wife was somehow erotic.

Finally Dan went in and laid in one of the guest rooms and I went to bed crawling in cuddling my wife’s naked used body.

That morning when my wife woke up she was incredibly horny and begged me to fuck her. I was apprehensive to enter her since she was filled with my friend’s cum but finally got in and had one of the most intense orgasms of my life as we both climaxed together.

She and I talked a lot about what had happened and how it occurred.

We remain good friends with Dan and our relationship has grown since the first encounter. My wife and Dan have hooked up together several more times since this night and we have had two threesomes together. Dan stayed with my wife for a week while I was out of town traveling and I thought it was nice that she had somebody there since I usually worried about her being home alone.

In retrospect, we agreed there has always been a sexual tension and dynamic between Dan and my wife but none of us knew how to approach it and feared of how it would impact our relationship. The alcohol lowered the inhibitions and things happened that had been in all of our minds for some time.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? We have only discussed this with each other and not anyone outside of the three of us.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It opened up a new area of our relationship and allowed us to explore areas we never would have discussed or talked about.

What was the WORST thing about this hookup? Not really anything bad.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has changed how we are as friends together and created an outlet for sharing intimacy that we would not have ever expected.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? We wish we had explored this area of our friendship earlier in our relationship but until a few years ago we had kids at home and it would not have been possible.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? This was our first endeavor into casual sex. We got married before starting college and were each others only sexual partner until this. We have talked about swingers since this happened but at the moment at least are very content and full with what we have. We may try to go on a swinger cruise or to fantasy fest next year to explore it further but currently it is just fantasy and talk.

What do you think about the Casual Sex Project? My wife found it and read some of the stories as she searched to see if others have done the same thing we are doing. It is nice to see people being open about their experience and she asked for me to share our story since it is anonymous.

You have a hookup story to share? Submit it here!