What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA – Iowa
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 1

Middle-Aged Threeway

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Dating casually

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? For the sake of the story I will refer to the other couple as Mark and Deb. I had met Mark and Deb through an online website for adult sex before many good apps were created. They were a couple in their early 40s who were looking for single guys who wanted to have fun in a male-male-female three way. They had a few pictures posted of them on their profile. She was 5’4” thicker, with some belly (from having 2 children) brown hair, small for her frame, breasts with large areoles and a small tuft of fur at the top of her puffy vulva. He was thinner 5’11, with silver black thinning hair and, a slim bit of flab on a light fur colored frame. He was fairly muscular with tattoos from being in the military. He had a good 6.5” length upward curving cut penis with a small set of balls underneath. His shaft was slimmer at the base but grew to average thickness at the head which was very bulbous. He was trimmed short. We had communicated through the built in email feature. We shared naked pics of ourselves and after a couple weeks of back and forth chatting we decided that we should voice call on the phone for a potential meet-up. They asked what I was looking for and I said just fun, safe experiences with a man and a woman. Mark asked if I’d be interested in male-male fun and I said that I’d definitely be interested, to which he replied coolly that we can see where the night takes us. I was nervous as I hadn’t met too many people on the internet up to this point so it was nice to hear their voices on the phone. It was a somewhat nondescript conversation that wasn’t so much on sex, but just seeing if we were comfortable with each other. From this call we decided we’d meet up Saturday night around 9pm at a business in their small town.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I drove to the location and parked in the alley. There was a string of business’ back doors and this was the only one with a light on. I walked over to the door and Mark opened the door and reached out and shook my hand. It was a nice greeting as he welcomed me inside and once I was seated, he locked the back door and slowly shut the blinds. Deb was in a chair and got up to give me a hug and kiss on the cheek. We all sat down and chatted a bit. They asked me how my drive was and we chatted about other small stuff. I used this to ease my mind as they could probably see I was a bit nervous.
After about 10 minutes Mark bluntly asked if we should continue this conversation with less clothes on. I said sure and Deb said of course. We move downstairs to the basement where there was an open room with some bedroom furniture but no bed. The place was a bit dingy, but my hard-on was definitely leading the way as they started removing their clothes. Mark grabbed an air mattress and unrolled it in the center of the room. He says we should set some ground rules and I agreed. We stated that condoms were required for penetration, stop means stop, and most importantly we all have fun. If it doesn’t feel right say something. We started to grab at our clothes as Mark turned the pump on the air mattress. I watch Deb remove her blouse and bra with her breasts coming into view. Mark was now ahead of her as he had already taken off his shirt and pants and was down to his red briefs. I remove my shoes, shirt and pull down my pants timidly while Deb was removing her pants as well. My boxer briefs are straining by my 6” cut erection. They both commented about how excited they are and could see that I was as well. I finish removing my pants and looked up at Mark as he pulled his underwear off and his helmet headed cock came into view. He was erect and it immediately thumps against his stomach. I pull off my underwear and my cock and smooth sack and heavy balls come out of their restraint. Mark chuckled and said he liked how smooth I was. My cock was straining as I watched Deb peel off her underwear revealing her puffy abdomen, dusting of hair and glistening inner labia poking out of her outer lips.

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? Mark said that Deb and I should get aquatinted while he finishes the mattress. Deb and I embraced each other with a hug while our hands roamed over each other’s bodies. It felt a bit odd since she is about fifteen years older than me and they did state that she had teenage children, but this is all gone from my head as she moves her hand down my side. She moved her hand in between us and proceeded to my cock and gave it a squeeze as I moved my hand down and inserted a finger along the cleft of her front searching for her clit. I give it a flick as she stroked my cock with us both cooing. Mark just watched as her and I slowly masturbated each other. He got the mattress all blown up and as he got up she sat down in front of me and licked the head and underside of my cock. Mark comes to stand next to me and she grabbed a hold of him and moves to start sucking him. She moves back and forth between each of us and finally pulls both of our dicks together in a very erotic way. Our heads are smashing one another and I’m leaking lots of precum. I put my hand on the side of Mark’s waist as he reaches down to touch his wife’s head and push her to suck us both. Now there is no way we both can fit in her mouth but she licks and sucks both of our heads together. He reaches down and takes a hold of my shaft, squeezing until a drop of pre-cum forms on my tip. He uses the tip of his finger to scoop it up into his mouth and says how young and sweet I taste. I ask Deb if I can suck on her pussy and she says yes and lies down on the mattress. As she gets on her back I dive between her thighs and lick from her upper thigh crease down to her pussy. I am now laying on my side and Mark kneels down and grabs a hold of my cock and sucks it into his mouth. He strongly sucks me and it feels really good as I’m licking and fingering his wife and she is getting very wet. I ask if I can suck on him and he states he was wondering when I’d ask. He lays on his side and I lay next to him. Deb sits on the corner of the bed and is rubbing her pussy as I look up at this hard dick right in front of my face. It was shower clean with no real odor. I stick my tongue out and lick his thick mushroom head and build up wetness on his shaft. I hover over the head and start to suck on him. He proceeds to suck on me again and we do this for a couple minutes. He says he’s close and wants to save it, so he gets up and Deb lays down on her back as if she knew what he was thinking. He hands me a condom and I cover my penis and crawl between her legs. I insert into her pussy and easily glide into her depths. As I’m slowly humping away I feel Mark grabbing my balls and shaft from between my legs and stroking on them. It felt amazing to have him hold me like that. He leans down and proceeds to rim my ass. I feel his probing tongue bath my ring in saliva. He stops this and asks to have a go at his wife . He has me grab his shaft and guide it into his wife. He fucks her for a couple of minutes at which point she grabs me and says she wants us both in her. We try to do this and we somewhat succeed both thrusting into her. She says that she needs a break and he asks if he can fuck me. I say yes and get on my knees in front of Deb and her husband grabs a condom and puts it onto his cock. I lean down and bury my face in her vagina as he licks my hole one more time, then puts some lube on his fingers and rubs my hole until he guides one of his fingers in. Up to this point, I have only had anal sex about 5 times and never with suck a thick cockhead. I was both tight and nervous as he plunged his finger in me, followed by one more, into me. He does this for a minute or so and then asked if I was ready. I tell him to go slow and he lines up behind me. I felt the tip of his head push firmly at my hole and it felt like a dowel rod. I tell him it hurts a bit and he fingers me more and smears on additional lube. He lines up again and I push out and feel his large head just jam into my tight ass. He is taken aback by how tight I am as he slowly plunges my ass. It hurts somewhat but I try to take it all and I’m shocked by the sudden switch from pain to pleasure. He starts thrusting in me in a manly way that made me feel like his chubby boy. Deb wanted back in and since I still had a strong hard-on she slid under me and I pushed into her. I let Mark control the thrusting and pushing. We went on for a couple minutes this way.
Mark told us he was about to cum and pushed deep into me. I could feel him gripping my sides as he came inside me. He pulled out of me and pulled the condom off his still hard cock which is now glistening in cum and cock sweat. I laid down and Deb climbed on top of me and rode me until I came a couple minutes later. I wasn’t sure if Deb actually had an orgasm or not. After some small talk and Mark describing himself as one and done, I looked at my phone and realized we had been down here for an hour. I took this as a sign when Deb started getting dressed. We all got up and said our goodbyes and I left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? It was exilerating but I was also paranoid people from my small towns around this area would maybe recognize my car.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To cheer myself up, Submission / Relinquishing power

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I had a lot of firsts occur and really found at this point I enjoyed being a bottom in a very submissive way.

What was the WORST thing about this hookup? That we didn’t hang out more again. I had a few invites but turned them down.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I do believe we all are entitled to having open consensual sex with each other and no one should judge.

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!