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What’s your gender? Woman
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Texas
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Marketing Manager
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)? 4
How many hookup stories have you here posted before? None

The outdoor concert was a wild one!

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? It started out as teasing my son-in-law’s brother, but turned into a very hot sexual encounter!

How long did you know the person before this hookup? For more than 3 years

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 young man was 17, the brother of our son-in-law. He is about 5’6″ tall, 145, brown hair and eyes and cute as can be, he looks like a virgin but a little doll! He used to come to our house when Rob dated our daughter in high school, he was probably 9 or 10 at the time. I had never even considered hooking up with him before. Afterward, I felt the desire to see him again as soon as possible to see what would happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At an outdoor concert where we were partying on the lawn. It was spontaneous, it was not something ever intended. I have never even looked at him like that before! We were at a concert at an outdoor venue. They had reserved seats but we purchased “lawn seats” since there were about 10 of us there. It was me, my husband, our daughter Ann, our son-in-law Rob, his younger brother Darryl, my brother-in-law Rick, our daughter’s friend Carla, Rob’s best friend Dave, my husband’s best friend Carl, and our neighbor David. Rick, David, my husband and I drove together and met the others there. We arrived around 7:00 while it was still daylight and all met up about 1/2 way up the hill, spread our blankets and started the party.

I was wearing some shorts and a blue shirt made of sequins, no bra, no panties. The shirt was one my husband picked out for me. My 36D tits stretched the material nicely and I knew my nipples were hard and poking out. My husband always wants me as “undressed” as possible and I wanted to please him. The shorts were very short cotton and they showed the details of my ass quite well. I was actually a bit embarrassed to wear this in front of my daughter, son-in-law because I felt I looked nearly naked but Steve insisted. I had no idea Rob’s younger brother was going to be there or I would never have agreed to dress like that. Our daughter has grown used to seeing me in skimpy clothes so I wasn’t concerned about her, but her husband had been a bit open in his interest in the past when I was dressed in sexy attire so I was concerned about that.

His brother Darryl was a senior in high school at the time and seemed to pay me attention on a regular basis. So much so that our daughter had warned me he had the “hots” for me! They arrived about 30 minutes after we did. I was shocked to see Darryl there but I had no clothes to change into so I tried to steer clear of him. The first band began playing about dusk. The crowd on the hill was standing so we all stood as well. Steve and Dave were standing beside me and we were dancing to the music as they played. We were all drinking and Dave eventually lit a joint. We don’t usually smoke weed but the atmosphere was right so I did. After getting a buzz Dave and I were holding onto each other swaying to the music. He asked me if I’d like to try a 1/2 hit of ecstasy. I was getting pretty high on the weed so I agreed. Darryl had moved over in front of us and asked to smoke some of the pot. Dave passed it to him and he started hitting it. By the time the first band had finished playing I was feeling very good! The ecstasy was starting to kick in and I felt a sense of euphoria like never before.

Dave has come on to me many times. He his just barely 21 but has been trying to make a move on me since he was in high school. I’ve always thought he was going to make a sexy man one day but he was still in the geeky stage in school. Steve went to get us a drink and Dave and Darryl kept me company while he did. The concert was very crowded and Steve was gone quite a while. The next band, the one prior to the headliner, started playing. Again everyone stood up and we were all dancing to the music. Without even realizing it, I was standing there with my arms around both Dave and Darryl. We were moving with the music and soon Dave was fondling my ass. Darryl’s arm was higher around my waist but he soon turned in front of me facing me and wrapped his arms around my waist. I was feeling no pain and realized I was quite turned on by these two young boys! As we danced I could tell they were both quite aroused, they frequently had their hard young cocks pressed against my body!

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? Steve returned with our drinks and Dave moved over making room for him. We smoked a bit more pot and I told Steve I was wasted, but I was really ok. I wanted to walk around a bit and told him so. Dave moved over to Rob and Ann leaving me with Steve and Darryl. Darryl was still facing me and said he would like to walk around some too. The 3 of us walked to the top of the hill and all the way to the back fence. There were bushes spread about 3 feet apart all along the fence and we walked between them leaning against it. I was standing between Darryl and Steve, both of them had an arm around my waist. Steve looked at Darryl and asked him if he’d ever seen my tits. Darryl seemed afraid to answer, but told him no. Steve then asked if he wanted to see them. Darryl didn’t say anything at first then said he’d always wanted to see them. Steve then told me to show them to him.I was shocked and didn’t know what to say. Before I could answer, Steve reached over and lifted my shirt over my tits! I was surprised to find I was turned on by this! Darryl didn’t say a word but his eyes were staring straight at my chest! Without thinking, I reached over and pulled Darryl into me hugging him, my bare breasts pressed against his chest. I held him tight against me and felt Steve move away and slide behind me. I was now sandwiched between him and Steve. Darryl’s hands slid down and cupped my ass, my tits still bare and pressed into him. Steve slid his hands inside my shorts and a moment later Darryl slid his hands inside my shorts also grabbing my bare ass with his hands.

Steve moved away leaving Darryl with me. We kissed and he eventually worked his way down to kissing my breasts. We were in a relatively public area with people walking by, but between the bushes against the fence, no one seemed to be paying us any attention. I reached between Darryl’s legs and grabbed his cock. He was totally hard and his shorts were already wet with pre-cum! The thought of this young man being so turned on by me was an incredible feeling! I knew we weren’t going to fuck, but I also knew I wanted to make sure he came. I continued to let him fondle and caress my breasts while I stroked his cock through his shorts. After only a couple of minutes, he tried to pull away, but I wouldn’t let him. I felt his penis spasm as he came in his pants, I was very close to an orgasm myself but pulled back before I did.

He was embarrassed at first, apologizing for his premature ejaculation. I hugged him and assured him it was ok and promised to help him get past that. Once he realized that wasn’t making fun of him he relaxed and asked if he could come to our house. I told him not that night, but maybe soon. After straightening our clothes we went back down the hill to the rest of our group.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? I was quite embarrassed at first, but soon realized that this was an opportunity to teach a young man how to make love to a real woman. I find him still as cute as ever and enjoy the times that I get to see him. The next day I was worried that I had taken advantage of him, and worried that he was going to tell his brother and my daughter, along with all his friends, what had happened. He called me the next day to thank me and promised, without being asked, that he wouldn’t tell anyone what had happened. He then asked if we could all do something again soon. 2 weeks later, Steve and I had several people over for a party and I decided to invite Darryl. This session was much more enjoyable for us all, and I had a chance to experience a true virgin in bed!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication, It was a first for me being with someone that much younger!

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish, MDMA, ecstasy, molly

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

How wanted was this hookup for you at the time? Somewhat

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? I told my best friend, Ellen, and my sister. Ellen was turned on by it, my sister seemed upset.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? Finding out that I am still found attractive by young men/boys! Helping an inexperienced person learn about sex.

What was the WORST thing about this hookup? Worrying that he regretted it or was going to brag to his friends.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I had never been with a man, other than my husband, since I got married…though I have flirted with many. I now know that sex and love do not have to be the same thing.

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

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

What do you think about the Casual Sex Project? I just stumbled across this site. I’ll have to research it further.

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

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