by lowercase

Gender: Male
Age: 49
Race/ethnicity: White
Current location: Pennsylvania
Highest education received: College degree (eg., BA, BS)
Occupation: Technical Management
Relationship status: Committed
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Experimental
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

Threesome – A Long Time Waiting

How long ago did this hookup happen? Last Night

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…)? Friends-with-benefits

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? My partner is a hot, little Italian girl, in her early 40s.  She has very perky D-cup breasts and an ass that rivals anything on the planet.  She is a very sexual woman that wants to experience many new sexual scenarios.

My partner and i have discussed introducing another male for MFM for a long time.  She would describe specific scenarios that she would like to try (some submissive, some standard MFM).   i approached one of my closest friends (who became separated recently) about being the third; he agreed.  He agreed but i could feel that he didn’t truly think it would happen and that it would be more a fantasy than a reality.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been discussing the threesome for quite sometime.  And since this would be the first threesome for all parties… we needed to be comfortable and communicative about it beforehand.  Much of the leadup had to do with scheduling and how the three of us needed to coordinate a good time. i decided to push for a date and told my friend to plan on this date.  i was the person that was handling all of the planning for the event.  i arranged that it would happen at my apartment.  i got some light food.  And i got plenty of alcohol.  Which we would need for this to go through.

i arranged the outfit that my partner would wear (a short, tight-fitting zipper down the front black dress, with stripperesque shoes, no panties) that she would change into after a couple of drinks. After a couple of drinks and an hour + of good conversation, she and i sat on the couch.

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 were on the couch and i was trying to have her open her legs a bit to give him a peek.  She was feeling a little uncomfortable and would keep her legs tighter.  After more and more conversation, i started to kiss her on the couch, in front of him.. i moved my hand up over her pussy and began to massage her pussy in front of him.  She was very wet and loosing up a little as she spread her legs wider for a good view.  After a while, i had her stand up and i unzipped her out of the dress in front of him.  i asked her if she want to suck him off and she said yes.

She kneeled in front of the chair as she put her head in his lap, took his cock out and started sucking on him.  i watched as she was sucking him; he was caressing her breasts and putting his hands on her head as she worked him.  On occasion i would go behind her kneeling body and rub her wet pussy.  He wasn’t getting hard enough to cum.

After a number of minutes, she turned around toward me. i had her stand up and removed her dress completely.  i asked her if she wanted him to eat her out and she said yes.  So i told my friend to get behind her and eat her out… he did with a big smile on his face.  She bent over an ottoman facing me while he buried his face deep into her ass/pussy.  She moaned and enjoyed that for about 45 minutes, cumming three times that way.  At one point, he mounted her from behind while we both fingercuffed her for a while.  But he couldn’t maintain the erection and went back to eating her out.

i came in her mouth as she came from him eating her out.

Did you have an orgasm? Did your partner(s)? i came twice.  She came five times (three by my friend eating her out and two by me after my friend left).  My friend never came.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No condoms.  He has been separated and hasn’t been with anyone and was married for a long time prior.  We did discuss it in detail.

What were your REASONS for having this hookup? She always wanted this as a fantasy.  She always wanted to have two men ravage her.  i’ve always had that fantasy too.. We are just trying to live out our fantasies before we’re too old to do it.

Were alcohol or drugs involved? If so, how much? We had alcohol.  It was needed and there was a fair amount.  No one was drunk but let’s just say everyone was well-lubricated.

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? After she came three times by him eating her out.. she went up and went into the bedroom.  i told my friend that i was going to join her and that he can let himself out.  Before he left he worried about what would happen to our friendship afterwards and i assured him that if this affected the friendship, we would stop.  As of now, we are planning for future threesomes.

To whom did you talk about the hookup? How did they react? No one.  We are being very discreet.

Was this a consensual and/or wanted experience for you? For your partner? Totally consensual.  We planned it for many many months.

Do you regret this hookup? If so, why? i don’t regret it and my partner doesn’t regret it.  It was an experience that we both looked forward to and it went off without any incident.

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? The best thing about the hookup was that we actually followed through with it.  We sort of knew it would be awkward.  But everything was good on my and my partner’s side; we came.

If there was a negative, it was that my friend didn’t cum.

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

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

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