Current location: Colorado
Highest education received: College degree (eg., BA, BS)
Relationship status: Wife
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 100 plus
How many hookup stories have you here posted before? None
Soccer Mom Escort
How long ago did this hookup happen? 2 years ago
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…)? Promiscous paid sex/fuck-buddies/Massage
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 worked as a soccer mom “massage escort”. I like sex, the touching and the intimacy involved. There were dozens of men over the course of a year or so that I was intimate with before I met my second husband. Some were older (early sixties) some were my age (early thirties) some were younger (early twenties). Some I saw only once and a few, who were attractive to me, I dated for a several months frequently engaging in sexual intercourse with them. Sometimes I was dating two or three guys at the same time and having sex with 2 different guys separately on the same day. The very first encounter I had sex with two guys at once. Later I did a one time gang bang with nine men at once for a bachelor party (three of them touched me and masturbated on me but did not penetrate me). My primary goal was to satisfy my own sexual appetites. I preferred having intercourse with guys who had a larger than average penis as I am able to easily orgasm with a big penis.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was getting a divorce but my first husband was still living in the house until we could sort things out. We slept in separate rooms. We had been quite sexually active during our marriage and I missed having sex on a regular basis a lot (I was in my early thirties and near my sexual peak). I was really desperate to be touched by a man, have him play with my boobs; put his cock in me and all the rest. My husband had a huge penis and he could always make me cum quickly with his big cock. So every few weeks I’d entice him into bed by giving him oral sex until he was so excited he would have intercourse with me. Having two kids to take care of made it difficult for me to meet other men. I later learned he was having a sexual relationship with another woman the whole time.
I became close friends with my neighbor, Hadley, who confided to me that she had a side business providing massages to men. She had strict rules. She would get nude with them and they could touch her anywhere they liked. But she only provided hand jobs. There was no oral or vaginal intercourse. She offered to introduce me to some guys she knew but also suggested I might want to meet with some of her clients for recreational sex. I would be in control of the situation and could go as far with them as I liked to satisfy my own sexual desires. A side bonus was getting paid for it. Initially. I found the idea repugnant and didn’t think I could do something like that. But one evening when my hubby had the kids and I was hanging out at Hadley’s she got a call. It was one of her clients and he told her he had a friend with him. He wanted to know if Hadley would like to meet them. Hadley was not comfortable alone with two guys at the same time. She was on speaker phone and I heard her (without my permission) tell him she had a friend who would be happy to meet his friend. She agreed we would meet them at a local dance club in Denver in an hour and see how things went.
Suddenly I was going to meet a stranger who was expecting to have intimate contact with me without having engaged in any preliminary social niceties. Based on Hadley’s protocol, shared with him by his friend, this guy would be expecting me to masturbate him and perhaps he would even play with me as well. The very thought of being felt up by a stranger made me wet. I was tired of my husband “mercy fucking” me so I thought what the hell. I could always just leave if I didn’t like it. Giddy with anticipation we got ready for our encounter. Hadley was my size and she lent me a sexy short silk dress. I had never considered going any place without panties on but at the last moment I took them off and put them in my little purse. The only clothing I wore was the silk dress. If he got his hand up my dress he was in for a surprise.
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 went to the club, it was called “Proof of the Pudding” and the guys already had a table for us. Thankfully the guy I was to be with was cute. His name was Brent. He was very polite and we had some drinks and danced. I could tell he liked me. After a bit we decided to go out to the parking lot (which was not well lit) get in the guys vehicles to make out. Brent had a pickup truck. Hadley was in the car next to us with her client, James. Brent began kissing me, putting his tongue in my mouth. Hot wet kissing. Soon his hands were on my boobs. My nipples got erect as he gently pinched them though the silk dress. I was already wet between my legs. I was sure he could smell my excitement. Thinking of this as a business transaction I boldly unbuckled his belt, unzipped his pants, reached into his underwear and pulled his penis out. I could tell he was a ‘big boy” even though he was not yet fully erect. I began to play with it and it got nice and hard. I glanced down briefly noticing in the semi darkness that it was thick and long, the kind of penis that provides me good stimulation during intercourse. As his erection grew I had trouble getting my hand around it. Soon he put his hand up my dress and he realized I wasn’t wearing panties. I was very wet. He began to finger fuck me really good and deep with two fingers while simultaneously pinching my nipples through the dress. Suddenly I was having a strong orgasm. I begged him not to stop. I came on his hand squirting as I reached my full orgasm. Slowly I recovered my composure and now it was his turn.
I knew he was expecting a good hand job so I began to tease his penis and rub it. I give super hand jobs. I began stroking him firmly and faster so he would cum and I could tell he was enjoying it so I was a little surprised when he asked: “I’ll give you an extra $100 if you suck me?” The very thought of sucking this handsome stranger’s big cock turned me on again. “Ok” I said. I put my head down on his lap and began to lick him gently. Then softly I took him in my mouth. I enjoy oral sex with the right guy. It’s different from guy to guy. It is always warm, salty spurts, but some are thicker and stickier and some are thinner and more watery. You can feel the contractions of the dick in your mouth and through your lips. It’s pretty hot. The actual taste isn’t awesome but the mental hotness of the situation and knowing the guy is feeling a lot pleasure at that moment makes it great. I took his hand and put it back up my dress so he could stimulate me while I sucked him. After a several minutes of hot wet sucking he suddenly groaned, grabbed my head so I couldn’t move away and began ejaculating in my mouth. I usually swallow and I didn’t mind. We put ourselves back together and went back into the club. Both of the guys looked satisfied and relaxed.
When the guys went to the bar to get more drinks Hadley said, “I saw your head bobbing up and down in the truck, did you enjoy sucking him?” What was his cum like?” She asked. “The things you want to know!” I laughed. “It was thick and there was a lot of it. It was like warm pudding. If he hadn’t been holding my head I would have made him squirt on my pussy. I let him fill my mouth before I swallowed it down…mmmmmmm” I joked.
Soon Hadley was ready to leave. This was just a job for her. I wanted to stay and dance with Brent. In the back of my mind I was thinking about what it would be like to spend the night with him. I’d already had a couple of orgasms in the truck but really wanted the full Monty. A good pussy pounding was what I was after. Brent offered me a ride home so I told Hadley it was alright for her to go without me. I had a few more drinks and soon both guys were sitting close to me in the booth. I was all over Brent and he knew I was interested in more sex. What I didn’t know was that when I went to the little girls room Brent had shared his experience with me in the truck with his friend, James. James had gotten a decent hand job from Hadley but he also wanted more. They both began feeling me up in the booth. They were taking turns putting their hands up my dress rubbing my moist pussy lips and teasing me.
Finally Brent asked if I wanted to go back to his place. I thought a moment and then realized that he was suggesting the three of us. I’d never been with two guys at once before. My unsatisfied pussy was saying yes, do it. I just nodded. We ended up at Brent’s condo, the three of us naked on a big king size bed. James had a shorter penis then Brent but it was thicker. Tremendous GIRTH! They were both touching me at the same time all over and then James was on top of me between my legs and I felt his thick penis rub against my pussy lips. I was begging him to put it in me. He buried it all in me, his huge balls hanging down – slamming against my asshole over and over. His ass cheeks clenched together as he twitched his cock inside me and I went crazy on his dick. “Ride ‘Em” Cowboy!” I encouraged him. I arched my pelvis up towards him and was rewarded by having a good solid orgasm as his firm penis filled me up and rubbed hard on my “G” spot. When he felt my vagina spasm he began to squirt inside me. As soon as James moved off me Brent replaced him quickly penetrating my well lubricated vagina. His huge penis felt so good. I was like a kid with a new toy wanting to feel how his large penis would feel in various positions. He was muscular and cute. I just wanted to mindlessly hump. I wanted to be fucked and ridden hard. I wanted to be used.
Brent pumped in and out of me for several minutes playing with my tits and squeezing my nipples until he felt me give it up and have several orgasms. My pussy was so fucking stretched, it was unbelievable.
He was really hot and bothered by now and he grabbed my buttocks thrusting deep and using the entire length of my pussy to get his satisfaction. It seemed he came for a long time. The bed was really wet from all my juices and both the guy’s cum. When I got up to go to the bathroom I felt copious amounts of semen run down the inside of my leg. Two guys had been there, one after another, was all I could think. It felt so good to be filled up like that. Having sex with two men was a kick. The rest of the night is a blur but several times I was on hands and knees with my butt in the air so one of them could mount me from behind and one could use my mouth. They must have been on Viagra because neither of them lost their erections even after they came. I thought about engaging in my fantasy of having anal sex but their penises were just too big to consider doing this. I did enjoy having multiple partners. In fact, I enjoyed is so much that later in that first year I agreed to a gang bang with nine men. They actually had a bowl of Viagra sitting on the coffee table at the bachelor party. The next day I thanked Hadley for introducing me to a new lifestyle.
Did you have an orgasm? Did your partner(s)? I had too many to count. The two guys had seven or eight between them during the course of the evening and during the night we slept together.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I was on the pill. No condoms as this was unplanned. I subsequently took precautions during later encounters.
What were your REASONS for having this hookup? I like sex, lots of sex!
Were alcohol or drugs involved? If so, how much? I was drinking but not to excess. I had enough to relax me but I was certainly aware of what I was doing at all times.
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? I saw Brent for a few months afterwards meeting at his apartment after work for sex. The sex was good but I decided we didn’t have enough in common. Once he took me to a secluded mountain location with wonderful views and we had sex in the back of his pickup. He had a mattress there. After a short break we did it again outside near the truck. He had me bent over totally naked while he fucked me. I braced myself on a tree. Being naked outside and getting screwed like that really turned me on.
To whom did you talk about the hookup? How did they react? I’ve told my husband and Hadley some things. My husband gets really turned on when I tell him these things.
Was this a consensual and/or wanted experience for you? For your partner? Yes
Do you regret this hookup? If so, why? No
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? I felt in control and liberated by these situations. The men were happy to have what ever type sexual encounter I agreed to.
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 or anything else? I’ll send details of later encounters later
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