Arranged Massage, Turned Threesome While On Vacation

by CentralPA

What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Harrisburg, Pa
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Marketing
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Dudeist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Curious on some levels
How many sexual partners have you had in your life (including oral sex)? over 100
How many hookup stories have you here posted before? none

Arranged Massage, Turned Threesome While On Vacation

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Group sex

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 girlfriend and I were planning a trip to Italy. Once the hotel in Rome was booked, I started looking online (Craigslist, before the Morality Police killed it) and found an Itallian masseuse who did outcall. To be fair, I don’t think he was a legitimate masseuse, or trained in any formal way – but his posting suggested he gives massages for ladies and/or couples. It was enough for me to bite, so I reached out. We talked via e-mail for a while about what I was looking for, what he was into, etc. He was very articulate and not rushing or pushing anything. He made me feel comfortable. He was willing to talk as much as I wanted about it and never pushed anything. It was all about “her pleasure” is what he repeatedly confirmed with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We settled on a date/time and location in Rome to meet. I told my girlfriend that I had arranged for us to meet up with a guy who lived in the area and would give us the inside scoop on what to see and do. She knows I like to talk with locals whenever possible. The best tips when traveling come from the people that live there, not the brochures.
In any event, we showed up on time and met Alessio, as planned. He was very likeable. We talked, laughed, and enjoyed each other’s company for a good hour (while consuming two bottles of red wine). I could see my girlfriend was completely loosened up, and I am well aware of what red wine does to her. It was falling together perfectly…
I gave Alessio the nod (which was previously discussed) for him to excuse himself and give us a minute alone. He knew instantly what to do, and said, “I must use the rest room, I’ll be right back,” and walked away. This was my cue now…
I slid my chair closer to my girlfriend and quietly said “Alessio isn’t a local tour guide… He’s a masseuse. I arranged for this ahead of time.” Surprisingly, she looked back at me and said “I figured that out about ten minutes ago.” I guess I’m not quite as clever as I thought. Probably due to the fact that I have mentioned this exact scenario during bedroom dirty talk more than a few times…
We were only a block from our hotel, which also wasn’t accidental. I told her to head back, take a shower if she wanted, and lay face down on the bed. Alessio and I would be there shortly for her massage. Just then, he returned from the rest room and smiled as she stood up and said “I’ll meet you boys back at the room”

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? Alessio and I stayed behind and gave her enough time to shower and be ready. We walked, with great anticipation, back to the room together. I opened the door and, to my delight, she was fully nude and face down on the bed. Just knowing someone else was seeing what I was seeing, and getting turned on by it was a rush in itself. This is something usually reserved for just me, but not this time…
He walked over, put his daypack down and unzipped it – pulling out some oil. I sat down on the chair, off to the side of the bed and said nothing.
Without much hesitation, he began massaging her back and shoulders. This went on for probably five minutes, before he began working his way down to her ass and hips. The more he massaged, the looser she became. Just like we talked about, he increasingly got closer to her ass and pussy with his strokes. Never really touching, but brushing past the areas that normally get left alone in a legitimate massage. As things progressed, I could see her arching her back toward his hands, as he rubbed her ass and thighs… getting ever closer each time until she was practically begging for it. At this point, I started to talk a little… I said, “You should see how wet she gets… I guarantee she is soaked right now.” It was kind of a verbal cue to say, go ahead, touch her there, and he did. She reacted exactly as you might expect. A lift of the hips, with a moan of delight to say, “yes, that’s what I want…”.
I have to say it was a little fuzzy at times, because of the amount of wine we drank. She must have rolled over and pulled him toward her, because in what seemed like a flash, they were kissing. I wasn’t expecting that, and at first it seemed like outside of the perimeter of what I wanted. Kind of, too intimate… in a weird way. But, I quickly adjusted and decided to go down on her while she made out with him. I love going down on a woman. It’s absolutely my favorite sexual activity, and the wetter the better. She did not disappoint there. I was in heaven. Next thing I know, she’s taking his pants and underwear off and sucking his cock. He wasn’t huge, but had nice size to him. Maybe slightly larger than me, if you take the uncircumcised part into account.
Needless to say, it was hot to watch. From there I remember him sucking on her breasts. She loved that, and it got her very worked up as she went back for more kissing. Again, it gets a little fuzzy at times, I know he licked her pussy for a little while, because I recommended he get a taste of what he was largely responsible for. I think at this point, I just watched.
Things kind of came to a crescendo as she told me to lay down and climbed on top of me. She took me inside her, facing away from me in the reverse cowgirl position. She knew she had two cocks to take care of, and this appeared to be her solution for that. As she rode up and down on my cock, she took him in her mouth. Looking up and seeing her suck his hard cock, while riding mine was very hot. I think he finished first, in her mouth, while I wasn’t far behind inside her.
The afterglow was celebrated with a bad Italian cigarette, shared between the three of us, on the cobblestone street – just outside the hotel entrance.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? Although she told me she wasn’t able to orgasm, the after effect was lingering and delightful. She was too worried about pleasing and maybe a little too nervous to cum, but did enjoy it very much. The dirty talk about the evening continues to this day on occasion. As for what she hoped for that maybe could have been different: She wishes it was slower. He was a little too eager to get to the sexual stuff. We feel good about it now. No issues. He also lives in another country though.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

How intoxicated were you? Drunk/high but not wasted

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? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

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

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

To whom did you talk about the hookup? How did they react? Nobody knows but 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? Testing the waters to see if it would be emotionally hard afterwards. The fact that it wasn’t, was great news.
Also, the lingering after effect of more good sex when reliving it.

What was the WORST thing about this hookup? He lives too far away, so we can’t repeat it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no

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

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

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? I wish more people accepted it, instead of treating it like a sin or defect.
Sex is a normal, biological need/desire. We aren’t programmed to go without it or only have it with one person forever.

What do you think about the Casual Sex Project? I think it’s great.

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