First Time Shared By My Boyfriend

by sexyjessie

What’s your gender? Woman
How old are you? 36
What’s your race/ethnicity? East Asian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Dancer
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Slutty girl!!
How many sexual partners have you had in your life (including oral sex)? More than 1,000. I stop count a long time ago, and I have always been an easy girl to fuck since this first time I was shared.
How many hookup stories have you here posted before? 3

First Time Shared By My Boyfriend

How long ago did this hookup happen? About twenty years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? First of Many

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? At the time, I was with my first ever boyfriend, and he was a couple of years older than me. The other guys involved were his friends, whom I already knew very well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the birthday of one of the friends of my boyfriend, and when I turned up to my boyfriend’s place, he and his friends were already quite drunk. They were drinking beer and smoking cigarettes. The plan was to have a few drinks there and then go to a club later on. I was wearing a short skirt, but not too short since this was China in the late ’90s, and had on a halterneck top, which showed quite a bit cleavage. I wasn’t wearing a bra, so my big boobs were very obvious and my outfit had already caused an argument with my parents that day. I also didn’t have panties on since my boyfriend always preferred me not to wear them.

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? So, as I said, my boyfriend and his friends were already quite drunk when I turned up. My boyfriend got me a drink and then had me sit on his lap since all the chairs and sofa were already occupied. He ran his hands up and down my legs and started to push my skirt up. I whispered in his ear to stop because I did not have any panties on and I was worried that my pussy would be visible to his friends. I tried to keep my legs together, but he was sitting in a way that made that difficult. He told me that all the guys would love to see my pussy so why not just show it. So after a short while, I gave in, and he pulled my skirt right up. All the guys were commenting on me, and I have to admit that the attention was making me wet.

Soon, my boyfriend started to ask all the other guys what they thought of my boobs. I have very big boobs for a Chinese girl. They are about 32G, and I definitely had the biggest ones they’d ever seen. My boyfriend started jiggling my boobs and rubbing them, telling his friends that they wouldn’t believe how amazing these things felt. Even I was getting horny, but I was also quite embarrassed by this and told him to maybe not play with me like this in front of his friends. He said it was just a bit of fun suggested that I maybe do something for the birthday boy. He was a virgin and had never see boobs before, and he told me that mine would be the best ones to start with. I told him, “Of course, I am not showing my boobs to your friends,” but he said that I was already showing them my pussy, so what difference does it make?

He doesn’t even wait for my reply and pulls my top up. All the guys’ jaws drop to floor form seeing my big boobs, and then my boyfriend asks the birthday boy if he wanted to touch them. I am about to say that he can’t, but my boyfriend says, “It’s okay, isn’t it Jessie? He can just have a quick play with your boobs.” I agreed and got up. I walked over to him and straddle him. He was hesitant at first but quickly started touching me. He was jiggling and rubbing my boobs and then started to kiss, lick, and suck my nipples. I was getting so horny! I pulled my top off and really started rubbing my boobs over his face. I could feel his hard-on through his trousers, and I started grinding and rubbing my pussy against it. Then, my boyfriend said, “You know what present he really wants. He is a virgin remember?” I don’t even say anything. I just stand up, take my skirt off, then undo his trousers, and pulled them down along with his underpants. He was already hard, so I straddled him and slid down on his cock and started riding him. I was a bit disappointed because he came really quickly, like after probably less than two minutes. Then, my boyfriend said that he was sure that everyone else wanted their turn with me. I hesitated a bit, but I was feeling really horny and agreed.

I had sex one after the other with the six guys, and then I finished with my boyfriend. It really felt incredible to have so many guys cumming in my pussy. Luckily, I was on pill because my boyfriend’s father was a doctor, so he prescribed me the pill, even though my parents were not aware that I was having sex yet.

After I stayed naked and my boyfriend asked me if it was okay that from now on I have sex with all the guys whenever they want. I said that of course it was. Then, he asked me about his other friends, and I just told him that I was happy to do it with anyone who wants to. So from that day on, for the next couple of years, until I moved to the UK to study and we broke up, I was having sex with any guy who wanted me to. It was really fun; although, I was probably too innocent to know it was wrong. But, I was really enjoying myself.

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? I did feel a bit dirty and used the next day, but overall, I enjoyed it.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it

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

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 a couple of my closest girlfriends, and they were so shocked by what I had done. They couldn’t understand how I could give my body to so many guys like that.

How would you best summarize people’s reactions about this hookup? Relatively negative

Did you get emotionally hurt as a result of this hookup? A little bit

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? It was the first time I was with multiple guys, and I discovered that I love to do that. From that day, I have been happy to use my body to get things I want, and it has made me a stronger woman.

What was the WORST thing about this hookup? Reaction of my friends and gossip about me as slut and easy, low class girl

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It introduced me to casual sex.

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

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

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 love it! It made me the woman I am today.

What do you think about the Casual Sex Project? Great site to share stories!

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