by Rachel
What’s your gender? Woman
How old are you? 32
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Director
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15+
How many hookup stories have you here posted before? 0
Anonymous Cocks
How long ago did this hookup happen? 2 years
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 have absolutely no idea what they look like. They are completely strangers to me. My FWB (male) found them on Craigslist before the Casual Encounter section is eliminated. My FWB claims that he selected guys based on the type that turns me on. I.e. Tall, athletic & fit, C-suit type, etc. The reality is that I have no idea how true his claim is. For all I know, they could have been my FWB’s buddies and I still wouldn’t know.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My FWB and I talked about this fantasy of mine more than once. That is, I wonder what it feels like to just let a total stranger fuck me. The challenge is that I know many people around town due to the nature of my job. So, there is no way I would risk my reputation & job for hookups like this. My FWB came up with the idea that he would do all the screening & selection of guys who would fuck me without seeing my face. My FWB planned & arranged the whole thing.
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? On the day of hookup, we got a hotel room. My FWB and I had sex first because I was so nervous and extremely horny from the anticipation. Then, when the time comes, I put on a blindfold, lied face down in bed totally naked and buried my face between pillows. I also have pillows underneath my tummy to prop up my ass higher to expose my pussy more.
When I was ready, my FWB went out to the hotel lobby to bring two guys into the room. As already instructed by my FWB, the two guys didn’t say anything to me. I only heard my FWB telling them to take off their pants, put on a condom & lube, etc. I heard some rustling of them taking clothes off, then I felt the first guy got on the bed and just inserted his cock into my pussy. I gasped at the moment a stranger’s hard cock just pushed into me. I moaned uncontrollably as the first stranger just pounded away at my pussy. Then, my FWB said to switch. The first guy pulled out and the 2nd guy took position behind me and penetrated my pussy without hesitation. 2nd guy pumped even faster and harder. I heard my FWB and the 1st guy cheered on besides me while the 2nd guy grunted with every long stroke that he tried to drilled down deep inside me.
As I was feeling my climax building up from the thrill of letting complete strangers cocks to ravage my pussy, the 2nd guy suddenly pulled out fast and splattered his hot cum all over my back. The 1st guy wasted no time and quickly resume the position behind me and began fucking me again. I could feel that he was not holding back either. He pounded fast & furious. Soon, he also pulled out and also sprayed his cum over my back.
Then, my FWB told me that it’s his turn to cum because it’s too exciting for him to hold it in. My FWB also didn’t try to hold back. He just unloaded inside my pussy after less than a minute of pumping. As I was feeling somewhat disappointed that I didn’t get to have an orgasm and my pussy was feeling a void, I felt someone inserted fingers into my pussy. I then heard one of the two strangers started talking about how sexually arousing it is to play with a sloppy pussy filled with cum. It was the fingering & probing motion that quickly carried me over the hump and I had one of the strongest orgasms I ever felt. I think my pussy was clenching so hard the guy was saying he couldn’t move his fingers.
After my orgasm faded, I heard the guy asked my FWB if he could fuck a sloppy second. My FWB asked me if it’s Ok. I was so horny and I wanted more. So I said Ok but without realizing the guy was asking to fuck me bareback. The guy inserted his cock and pumped away while praising how slippery & how hot & tight my pussy felt. After a few minutes, I heard the guy yelling he’s going to pump another load into my pussy. That’s when it dawned on me that he was fucking me raw. It was too late. I already felt his cock convulsed and he pulled out.
With my head still buried between pillows, I felt their hands pulled my ass chics wide apart and followed by fingers entering and probing my now cum filled pussy. All three guys were commenting about how sexy my creampied pussy looks.
I heard my FWB asked the other guy if he also wanted another go at my pussy. He said that he’s done. So, my FWB told them to leave.
After those two guys left, I got up. Stood in front of a mirror to check out my cum-covered back. My FWB stood behind me, pulled my pussy open to let me see cum dripping out of my pussy and running down my thighs. My FWB using the cum as lube to start fingering my clit until I had another screaming orgasm while standing in front of the mirror.
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 was so thrilled about the whole experience that I asked my FWB to arrange similar plays another 5 times during the following 2 years. Once, he brought as many as 4 guys to take turns on me. But we never let guys fuck me bareback again.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Birth control pill / patch / ring / injection / implant
What were your motives for this hookup? Fun, pleasure, horniness
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
To whom did you talk about the hookup? How did they react? Two of my best female friends. One said that she wants to try it too. The other thought it was yakki.
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
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Sexual thrill
What was the WORST thing about this hookup? Worry about STD
All things considered, how POSITIVE was this experience? Very positive
What do you think about the Casual Sex Project? Excellent
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