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What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 28
How many hookup stories have you here posted before? 1

Threesome with the masseuse

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

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? The first partner was H, whom I talked about in the first story (‘end of a friendship’). 28 y-o, tall (5ft9-ish), blonde with long hair. A pixie personality. A thin figure with small round breasts and a nice backside bump.
The second partner was my Chinese masseuse M. She was a strict-looking girl at first with glasses and her black hair in a ponytail. Average height and build. I have not been with many girls from that part of the world but I think she was busty in comparison. I would say she was in her early to mid-20s.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The background was described in my previous story. H. was my good friend (best friend) and we had hooked up a few days before during our trip together. We never did talk seriously about what it all meant though. Me, out of shyness/wanting to look ‘cool’ I guess. Her as a kind of weird defying behavior to show we could have great sex every night but it didn’t go further for her? In any case she did all she could to avoid this morphing into a relationship, for example talking to me about guys or other friends she was attracted to. I now think of it as a prelude to the unpleasantness that followed (see the other story).
One evening, we had decided to get a massage as a hotel nearby had a good reputation and prices were really cheap in the country. Once at that hotel, two people came to pick us up in the waiting room, a guy for H. and my masseuse, M.
M. acted very professional during the massage, but by the end started to make comments about how good I looked while touching my body… I’m happy with how I look and confident enough, but I’m no model, so I was taken aback and started to think maybe she was angling for a ‘happy ending’? I had no special interest in anything transactional (if only because I had been having some great sex with H.) so I just thanked her and moved on at the end of the session.
After that H. and I went for dinner nearby and talked about the massage. When I mentioned M’s comments she jokingly asked me about the happy ending and I told her my thoughts. She said I was an idiot, that M. was clearly into me and that if I didn’t want a quickie blowjob then I should’ve convince her to come to our room for more… I felt a bit awkward as I didn’t know whether she was serious or just performing her ‘cool’ act again. I didn’t show it and upped the ante by joking semi-seriously: “You’d be bored if I were having sex with that girl in our room. Maybe you should invite your massage guy back too and go at it on the other bed.” She laughed and replied she thought about it at first but her “gay-dar” told her he wouldn’t be interested in her. However, she added, she’d love to fuck little M.! Again I didn’t know if I should take this as a joke or as a serious invitation for a threesome… I did know about some bisexual tendencies at least as H. was keen on commenting on women’s bodies. Anyway, I won’t say I wasn’t very excited by the idea so I went for it and assumed it was 100% serious – which it turned out to be. H. instructed me to go back to the hotel, just one block away, ask if M. was still there under some random pretext as if I had forgotten my watch, and proposition her.
15 minutes later, thinking to myself I really was living a crazy week, I was in the salon and quickly found M. She flashed a big smile that seemed a bit more than just commercial, which encouraged me. I was as direct as can be, also because her English wasn’t great and I wanted to make myself clear. To my surprise, H. was right and M. was straight away into it, just playing shy for a minute, then asking me if my hotel was far.
At that point, she looked embarrassed again and asked me about my “wife”. I laughed and said she wasn’t my wife, nor even my girlfriend, but that the whole thing was her idea anyway, adding that she would be there as well for the fun… I gauged M.’s reaction. She didn’t look like she was used to this kind of proposition, but as far as I could read her, she was thinking it was an experience to try once…
She said she’d need a little time to change and prepare and would join us.

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? 30 minutes later I was back at the hotel, already extremely excited by the perspective, making out with H., who found it funny to turn my arousal to 11.
When M. knocked on the door and we opened, I felt a bit like a cliche of an experienced couple “initiating” a young, exotic girl in their depravation.  She looked very innocent with a below-the-knee dress and very little make-up, although she wasn’t wearing glasses anymore and her hair was free of the professional ponytail.
H. took control and made M. comfortable, offering her a drink from the mini bar and talking to her. After some chitchat, she told her she’d heard how happy I was about my massage and complimented her. M. shily thanked her and asked if she wanted a massage too. Of course, this is what H. wanted and they were both understanding each other very well.
At that point, though, H. did something neither M. nor I expected. Instead of getting ready for her massage privately, she stood up in front of M., dominating from her tall height, pushed away the straps of her light summer dress and let it slide on the floor. Then she unhooked her bra, and let her small but firm breasts out, a few inches from M.’s face who this time was really blushing – and not out of ‘fake’ shyness. As for me, I was mesmerized by that very sexy scene…
H. then went lying down on the bed on her belly with just her laced pink panties. M. kept all her clothes on but made clear it wouldn’t be a professional massage by climbing on top of H., spreading her legs and moving her dress aside to sit on H.’s butt. She then massaged her back and legs for a long time while H. was moaning lightly at first, then in a more and more sexual way.
After 20 minutes or so, she stopped M. and rolled to face her. She said she enjoyed the massage and wanted to thank her her way. Then she started pulling down the zipper on M.’s dress. M. knew what was going on of course but still seemed quite shy about being undressed by another woman. I was still a spectator and got a jolt of excitement at discovering M.’s body. She was wearing white underwear, as vanilla as can be. H. who was now sitting down on the bed immediately buried her face in M.’s breasts and put her hands firmly on her ass.
This is the moment I chose to get into the action. Still fully dressed, I went in M.’s back and started kissing her neck lightly while I was unhooking her bra. That revealed two beautiful heavy breasts, with very dark nipples that were extremely erect by that point. At the same time, H. was lowering M.’s panties and right after removed her own. That’s when she felt she had to slow it down; she took M. by the hand to come sit next to her and started making out, french kissing her frankly and taking the lead. I took the opportunity to get off my clothes in the meanwhile, more excited than ever. Seeing that H. told me to approach and grabbed my dick. “Do you like it?” she asked M., who smiled and opined. Then H. adopted her most teasing expression, kind of fake innocence and provocation, and started sucking my dick while looking at M. the whole time. After a few thrusts of my penis into her mouth, she used her other hand to grab M. by the neck and gently push her face down to her tits. M. got the message and started licking and kissing H.’s small red nipples, making her moans louder. Then for the first time, M. took the initiative, raising her head and signaling she wanted to give me oral now. She was excellent at giving that blowjob – which convinced me her innocent demeanor was a bit of an act – and H. played with her breasts the whole time – so different from her own. She was massaging them, pinching the nipple, playing with them, ultimately working her way down and, while still licking and biting M.’s boobs, put her hand nearer her ample bush and started lightly fingering her. The scene was too much for me and I said I was gonna come soon. M. confirmed with a series of nods she was ok for me to come in her mouth, which I did, abundantly.
The girls continued to make out and caress each other while I was recovering. M. wasn’t fully taking care of H. though, probably due to inexperience with women, so I decided that the fastest way to get hard again would be to work my tongue on H.’s pussy for a while. Now M. seemed to enjoy watching that and was gently playing with her clit. Fully hard again after a few minutes, I grabbed a condom, put it on, grabbed H.’s legs and pulled her towards me as she yelped in surprise. I slowly put my dick into her until her nails were firmly stuck in my back. M. now got close again and started playing with H.’s tits but H. wanted to take this to next level and told M. to come sit on her face. M. timidly executed and sure enough, I was watching my friend work her tongue in the thick bush of that Chinese girl while I was fucking her. It didn’t take too long for me to come at this rate… But I still wanted H. to get her due so I started working her G-spot with my finger while she was still fucking M. with her tongue… H. quickly came but M. still seemed a bit too tense to come from her licking. I tried as best I could to make my dick a bit hard again and brought it to M.’s mouth, standing up on the mattress where she was sitting on my friend’s face. M.’s oral attention quickly made my cock fully operational again. I thought I had to give her full service now as she was our guest after all and was curious about girl-on-girl sex, but not yet fully relaxed about it. Plus she was the only one who hadn’t come.
I took her gently off H. who was about to have a jaw cramp anyway I think and positioned her on all fours. I put a condom on and placed my penis right at the entrance of her pussy and played around for a while, making her more excited. Then I pushed in… That pussy was one of the tightest I had been in. Having come twice already certainly helped as I’m not sure how long I would have lasted otherwise. I think the female stimulation, even if it was unusual for M., had worked wonders as she started to come after a few thrusts, and for the first time of the evening was frankly vocal about it, moaning, huffing and puffing. H. had retreated to one of the armchairs and was watching, playing with her clit and coming more herself. Finally, in one violent thrust, I came into M. and we collapsed on the bed.
After some cuddling and a shower, but no talking, M. left, french-kissing both of us in turn.
H. and I, still naked, just lied down in bed and reveled in the moment, talking about how amazing it all was. Incredibly this got ourselves back to arousal and I fucked her one last time that night, doggy style.

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? There was never any pretense to see M. again as we were moving to view another city on the next day.
As for what happened after with H., I described it in the first story I posted.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? Very

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

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? The amazing sexual experience. I’ve had a few threesome but I think it may be the best.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It encouraged me to be forthright about what I want. I’d never had propositioned M. for sex (especially for a threesome) if H. hadn’t been goading me. But she was willing and wasn’t enthusiastic during the act. After that, I hesitated less about saying what I want. I got rejected many times but who cares when it’s a stranger I’d never see again?

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

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

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