This post is sponsored by The T Bar.
What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? Cambridge, MA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Part time massage therapist, full time IT manager
What’s your current relationship status? Single
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? approx 80
How many hookup stories have you here posted before? None here
My Key to the Swingers’ World
How long ago did this hookup happen? Day before Saint Valentine’s day
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? I met a married couple who are swingers, whom I met once before. They’re in the 50s, they are in good shape and can be considered good looking. I met them thru a swingers website swinglifestyle.com in the past. My username in that site is the same as my pseudonym here. It’s only visible to single women and couples. I originally reached out to her husband to find out whether he’s like to treat his wife to a full body massage with the possibility of having a happy ending.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As with most of the massages that i give to married women thru the swingers website, we exchanged a few txt messages to decide where to meet. They booked a hotel room near Boston, MA. I showed up in the evening. We talked for about 30 minutes to catch up since the last time we were together. Last year we tried to meet several times but due to scheduling conflicts we couldn’t make it happen.
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? I set up my massage table, asked here where she had tension, so that I could address those areas prior to trying anything sensual or erotic on her. I watched her get undressed. She was wearing sexy clothes, just as I had suggested to her husband prior to getting together. It was nice to see her remove her bra, her long stockings and also her panties. During her massage I wore a t-shirt and shorts.
I started with a relaxing massage, with her face down, to get rid of any tension she had on her neck, upper back, shoulders and lower back. She was quiet during all this time. At times she’d simply utter a few sounds to tell me where it felt good when I massaged her.
Once she was completely relaxed I started to massage the side of her waist, making sure to stimulate that area that feels so good when getting it massaged. I tried to produce similar sensations to the ones when a person moves their hands along the sides of your naked torso, which give you gentle sensations of arousal. Once I noticed she was getting aroused, I started to massage her gluts. She loved that as she has had some sciatica nerve pain. Plus, the sensation of my hands working on her round behind, made her feel even more aroused.
As the massage progressed I could see how she started lifting her behind, as a sign that she was getting more and more aroused. At one point, I asked her to spread her legs apart so that I could start massaging her inner thighs. I massaged that area vigorously, so that she’d feel my hands getting closer and closer to her pussy, but without touching it. I did this for several minutes as a way to tease her. I never give a woman what she wants right away. You always want them to ask you for more.
As I continued to massage her inner thighs and noticed that she was getting slightly wet, I decided to come closer and closer to her outer labia to build more anticipation on her. I could notice how her breathing was getting heavier and how she started clutching the sides of the massage table. That showed me how intense were the sensations of pleasure she was enjoying. At this point, her husband started to kiss her, which made her even more aroused, as she was channeling her arousal towards her husband. After several minutes she started pulling her husband towards her. He was standing up, so you could tell that she really wanted to suck some cock. Her husband quickly got undressed and she put his cock in her mouth, which made her enjoy the experience even more. At this point I also decided to undress myself, while still trying to maintain the stimulation on the outside of her pussy.
Once I thought it was a good time to try to reach out for her clitoris, I did that. I used my right hand middle finger to stimulate it non-stop. I could tell how the intensity of that made her take a break from sucking her husband’s cock, but she made sure to keep her right hand still holding on to it, so that she could easily suck it once she felt like having something warm and hard inside her mouth.
In order to bring even more pleasure to her, I placed one of my hands underneath her, so that I could reach her clit with the tip of one of my fingers, then I used the fingers of my other hand to play with the outside of her pussy, as a way to tease her, because I knew she already wanted to have something inside her pussy. Since that desire was so intense, she’d sometimes push herself towards my hand, so that my fingers would go inside her pussy, but I knew her wanting more and more.
When the time was right I inserted a couple of my fingers inside her pussy, and I could hear a sigh of relief from her, at the same time she spread her legs apart even more, as a way to ask me that she wanted even more. I focused on finding her g-spot, which I quickly did. The simultaneous stimulation of her clitoris with one hand, and the g-spot with another, while she sucked her husband cock was exactly what she was dreaming of. I made sure to vary the intensity of how fast I stimulated her, so that she’d get closer and closer to reaching an orgasm. At one point her moaning was telling her that if I continued doing what I was doing to her, she’d reach a delicious orgasm. I kept doing that until she finally squirted a little bit. I felt that quick sensation of warmth liquid on one of my hands. I told her husband that she was squirting, which made him show a big smile.
At one point, her husband asked her to move to the bed, so the three of us went there. She was in between the two of us, face up. She wanted us to be close enough to her so that she could take turns sucking her husband cock, as well as mine. That was so hot! After a while she started talking dirty, saying that she wanted to have some warm cum on her mouth. That got me extra hard as I was already imagining her swallowing my cum. In order to get myself more aroused, I placed myself in such a way that I was stimulating her g-spot with one hand while jacking off with the other. That way I knew that he talking dirty came from actually being extremely aroused at the same time. I continued with that for a while, until I decided to bring her even higher with her sensations by also putting the small finger of my hand, the one that was stimulating her g-spot, in her ass. As I started playing with the outside of her ass, I could feel her anus contract and relax as if she was ready to have my finger inside of her. At the same time I could see how her facial expression started getting more intense. I gently started inserting my pinky finger on her ass, I had my ring, middle and index finger on her pussy, and I started using my thumb to stimulate her clit. This was the point that got me so aroused that I could feel how I was ready to cum…When I knew that I was about to cum I told her to come closer so that I could come on her mouth. I felt that amazing sensation of cumming, while at the same time watching her swallowing that! She sucked it dry and felt amazing. Her husband took several more minutes before he cum in her mouth too. She was a happy woman, having swallowed to loads of cum while she was so aroused.
We took a break in bed. She was in the middle and the two of us, were by her side. After about 20 minutes I started getting ready to head back home, cleaning, folding and placing my massage table in its case. I got dressed and wished them a Happy Valentine’s day!
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, 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? They stayed in their hotel room. I headed back home. We’ve done this before. Since both of them are in love with each other, they probably felt very happy. I was pleased to make them feel more in love.
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
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
To whom did you talk about the hookup? How did they react? There are a couple of male friends who are always interested in knowing about my latest massage experiences.
How would you best summarize people’s reactions about this hookup? Relatively positive
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? Being able to make a couple continue to enjoy more sexual intimacy with a little help from my massaging skills.
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 simply reinforces what I already do with couples or single women in the swingers community.
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? I do something similar to this at least once a week. Sometimes it is with new couples, other times with couples I’ve gotten together before. I also find women to massage thru tinger. It’s all about making others and myself feel good about our encounters.
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 was kind of shy for a good part of my life, so I feel as I have more than caught up with what I was missing in life, in terms of adult fun.
What do you think about the Casual Sex Project? It’s an interesting place to really find out what’s happening out there with people who are enjoying sex.
You have a hookup story to share? Submit it here!