by TM

Gender: Male
Age: 43
Race/ethnicity: White English
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Own a PR Firm
Relationship status: Married
Religious affiliation: Catholic
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? A Few

Dinner For Three

How long ago did this hookup happen? A Year

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Threesome

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? I had two partners the night this happened.  The first was Maggie, my wife.  She is tall and in her late twenties, with long black hair and pale skin.  Back then she was really thin but still had a nice pair of C cups.  We were introduced by a mutual friend and had been together a little less than three years and married just over a year.  People were unsure of my dating and being married to a woman I am fifteen years older than.  I love her.  One thing to share, Maggie has a high libido and is quite adventurous sexually and is much more what I need in a spouse than my first wife.
The other was Sandra, my workout partner.  She is about five six, with long blonde hair and in her early thirties..  She is very fit and quite muscular, even has a six pack.  After I had gotten married I had moved into a new house with Maggie and had to find a new gym.  I had put an ad up for a new workout partner at a gym a few blocks from my house.  Sandra had responded and I had worked out with women in the past, I have found I push myself a little more and workout a little harder somewhat to show off for a woman.  I knew Sandra was bisexual, in the year we had worked out together she had dated both men and women and I had seen her picked up by both after we worked out.  Sandra was very open about her sex life, probably a bit too much and I knew more than I wanted. I was a newlywed when we met and had never thought about her sexually even after seeing her naked once.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This actually took a lot of planning over several months.  Maggie and I actually have a great and exciting sex life and seemed like we were always trying new things.  Now Maggie was the one who first brought up having another woman join us in the bedroom which was a little surprising for me.  I was against the idea at first for two reasons, first some twenty years ago I had a threesome and it wasn’t that great.  Second a friend of mine was in one, and his partner ran off with the other person.
However I did come around after Maggie and I discussed it a little more.  Now this part is important, you have to find the right third person.  This was a bit of a search and Maggie had one failed approach.  I didn’t think of Sandra right away but Maggie saw her one day and made a few comments about her physique and we discussed it and made the decision to approach Sandra.  Maggie had met Sandra a few times
I mentioned it to her a few days later and Sandra admitted to a bit of an attraction for me.  However she had a boyfriend at the time and said she was a lot of things but not a cheater.  Maggie was disappointed but I told her to wait, Sandra never stayed with anyone for long.  I was proven right a few weeks later as Sandra broke up with her boyfriend and approached me about joining my wife and I in the bedroom.
I had promised her a good dinner and it took much of a Saturday for me to prepare it.  Maggie and I dressed up, just a dress shirt and pants for me and a tight little black dress for Maggie.  When Sandra arrived she had on a sleeveless little red dress that accented her muscular shoulders and arms and showed a bit of cleavage.  I could tell right away she was not wearing a bra (other than a sports bra when we worked out together I am not sure Sandra ever wore bras).  We ate dinner and chatted a bit, I could tell Maggie was pretty nervous.  After dinner we finally moved to the bedroom.

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? This was a pretty kinky evening. Once in the bedroom Sandra asked me to help her out of her dress and I unzipped and it fell off and confirmed she was not wearing a bra and only had on a tiny black thong.  She turned and I got a good look at her breasts and we kissed a bit.  Maggie was watching, still a bit nervous as Sandra unbuttoned my shirt and undid my belt, Maggie would later admit seeing me with another woman was getting her.
Sandra asked Maggie to pull her thong off and she did so, both Sandra and I had to make it a point of asking and including Maggie as she was quite nervous and had never been with another woman.  Sandra then undressed Maggie and they made out a bit and seeing my wife with another woman was getting me hard. I kissed Maggie on the back of the neck a little and swatted her as she was mounting Sandra.  I then kissed Sandra and played with her breasts a little and then penetrated her.  I rode her for a bit until I was close to coming and then pulled out and finished inside Maggie.
I had to lay there for a bit, I was a lot older than either woman.  Maggie and Sandra played with each other for a bit, kissing and Sandra gave Maggie oral until she came screaming quite loudly.  All three of us then laid there for a bit in some kind of post sex bliss.
We went one more time, this time as I laid there Maggie started kissing me facing the opposite way and letting her boobs hit me in the face as Sandra gave me oral. Sandra mounted me and rode me in cowgirl and Maggie pulled back a bit to watch.  I tried to get Sandra to stop but she wouldn’t, and I ended up dumping a load inside her.  Sandra also had an orgasm and I ended up fingering Maggie until she came.
We laid there for a bit, all three of us were quite content and had enjoyed ourselves. We talked about random things and I think it was around one or so that Sandra made the decision to go home.  She kissed both me and Maggie goodbye and made a point of telling us she had quite enjoyed us both and hoped to join us again.  Sandra then went home.

Did you have an orgasm? Did your partner(s)? I did twice and Maggie did twice as well, but I think it was just the once for Sandra.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Sandra is allergic to latex, but she had recently tested clean and showed us the paperwork and she was on birth control.  As for Maggie, she was my wife so I wasn’t worried about it and in fact, we were even trying to get pregnant.

What were your REASONS for having this hookup? Maggie and I both wanted to both have someone join us in the bedroom, if Maggie hadn’t brought it up and instigated it I don’t think I would have.

Were alcohol or drugs involved? If so, how much? A glass of wine each for me and Sandra, and I think Maggie had two

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Maggie and I had Sandra join us two more times in the bedroom and once in a hot tub as we had rather enjoyed our night with her and Maggie was much more into it.  I think this would have become a regular thing had Maggie not gotten pregnant a few months later and her libido went way down.  Sandra is someone we enjoy together so I won’t touch her unless my wife is there.
Sandra and I still work out together a few days a week, not as much as she is past me physically now and can bench more than me.  She has asked a few times about joining us again but has figured out as I said, she is someone my wife and I enjoy together.  Maggie is now almost eight months pregnant and I am not sure if Sandra will be joining us in the bedroom again or not.

To whom did you talk about the hookup? How did they react? I haven’t told anyone, what goes on between a husband and wife in the bedroom is private.  I think it is part of the reason I shared it here.

Was this a consensual and/or wanted experience for you? For your partner? For all three of us yes

Do you regret this hookup? If so, why? Not at all

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best part was a great evening with two incredible women and that my wife was the one to even bring the idea up.  As for a worst part, I would think that would be that I am pretty sure Sandra will not be joining Maggie and I again.  Not sure this changed how I feel about casual sex but I would say this was a much more enjoyable experience than my first threesome.

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 or anything else? Since this will be my last post for now, I did want to offer some advice to anyone considering having a threesome.  I found the experience with Maggie and Sandra rather enjoyable but a few words of caution.  Maggie approached a friend of hers about joining us first, the conversation did not go well and I think she misjudged her friend’s sexuality a bit and they have not spoken since.  Second make sure it is someone both you and your partner are comfortable with.  Finally be sure about your partner, I had a friend who had his wife run off with the other woman.

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