A Series Of Sober Conquests

by Caldwell

What’s your gender? Man
How old are you? 41
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
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Active with a capital A
How many sexual partners have you had in your life (including oral sex)? 75+
How many hookup stories have you here posted before? 1

A Series Of Sober Conquests

How long ago did this hookup happen? 4 nights ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? Pretty, petite, 33 year old blonde. Met on Hinge while I was in Chicago on business. We never hooked up while I was in town but kept chatting after I left. She revealed that she was coming to NYC for her own business trip and agreed to a date on a Saturday. The chatting started off spiritedly but as it continued I felt like she wasn’t really into my personality. I was being pretty funny and she either seemed to not get it or not like it. She also came off as quite vapid and I started to fear that the date would go sour. I don’t drink and there’s pretty much nothing worse than a stale date with no booze to hide behind. I actually texted her to see if she wanted to cancel. After she referred to my question as dickish because clearly she was attractive enough to have another date and had chosen me instead, I apologized and recommitted to meeting. Amazingly she still wanted to go out with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The date turned out to be fine. She is pretty hot and definitely a spark plug which kept things interesting. I took her to dinner at a hotel restaurant and after dinner we went to the rooftop bar for another couple drinks. We started making out, which for the first time, as a sober activity, turns out to be mildly thrilling. Without the edge-erasing power of alcohol, one must be pretty bold to lean in for that first smacker. Then the negotiation to go further began. She clearly wanted to fuck but was hesitant because I think it had been a while. During dinner she had brought up a couple of terrible dates back in Chicago that ended up going no where. I made it clear that there was no pressure but that the offer to come to mine stood. She was appalled by the idea of going back to Brooklyn, which matched up perfectly with the posh persona that she loved projecting. Ultimately, the Brooklyn sojourn was kind of exciting for her, if I may be so bold to say.

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? She had the most adorable little romper on. With not a lot of difficulty I took it off once she got on my bed. She was impossibly little, probably the most petite woman that I’ve ever been with. She is also the first sexual partner in years to not go down on me at any point during our session. I was excited to fuck someone new so there were no complaints, but it was notable. I went down on her instead and she tasted good, squirming and purring. On the loud side which matched her personality. I put on a condom and slowly pushed my rock hard cock into her tiny pussy. Her vagina is the tightest I’ve every experienced. It was so tight, and her curves so surprisingly squeezable, considering her small frame, that I came like a high schooler – fast and without power. I couldn’t believe it. I actually tried to swap out for another condom and keep fucking, I was so embarrassed, but that only lasted for a minute. I went back down on her and made her cum. She didn’t mention my performance and we talked for a while. After about a half hour we started making out again and she straddled me, stuffing my hardening cock into her little puss. I stiffened right up as she rode me. Then she made a face and told me that I was asking for another kid. I moved her off my shaft and put on another rubber and started fucking her missionary. I lasted a respectable amount of time during this round and gave her a good pounding. She looked really good while I fucked her. I ended up flipping her around (she was fun to throw around, being so light) and fucked her from behind, grabbing her pert butt, watching her breasts ripple while I fucked her until I came in the condom.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, more than 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? I only say somewhat because of my shockingly poor first round. As is usually the case, it’s thrilling to be with someone new. I felt funny about the whole thing considering that I don’t think I actually like this person. It’s one thing to fuck someone you don’t have a future with. It’s another to fuck someone whose personality is actually repelling.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, Power / Dominance, This was my first conquest in a planned week of fucking four different women on four consecutive nights.

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

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? I told three friends. They were intrigued by the near cancellation turned conquest and impressed by the streak.

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Fucking someone new. Her tight pussy made me feel big and powerful.

What was the WORST thing about this hookup? Cumming so god damn fast.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I probably will not actively pursue sex with someone that I do not like again.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? The next night (Sunday) a FWB came over. We have been fucking for 9 months, first dating then as FWBs. We went out to dinner, watched some tv then fucked. We are very well matched, sexually. I don’t know if I’ve ever been with someone who I can make cum so easily, so frequently. She always gets me off too and is very good and taking instructions. She’s become an excellent cocksucker and loves to be pounded different ways. She is 29 with perfect breasts and a chubby little butt. also blonde. We fucked again in the morning. During coffee she began crying and told me that she couldn’t continue on as FWBs anymore and that she loved me. I felt badly that she felt badly but I’ve always been very straightforward with her about my feeling that we weren’t a romantic match.

On Monday night I went to dinner with two buddies. Another FWB, who is insatiable in bed, literally horny at all times, texted me to hook up. I gladly agreed as my planned fuck buddy for the night had backed out due to her period. She came over by 10 and we immediately went at it. She is awesome in the sack and has a fantastic body. Brunette, curly and curvy yet petite. Did I mention how much she loves sex? We fucked again in the morning before she left. She is 34.

On Tuesday, I met a woman that I’ve just started seeing. Things have escalated very quickly between us. She is beyond impressive in many ways, absolutely gorgeous, funny, smart and has an incredible sex drive. She is also one of the most talented fuckers I’ve ever been with. I may be falling in love. We had an incredibly hot evening at her place and repeated ourselves in the morning, capping off a groundbreaking (at least for me) 4 days of sex. Half-Asian, half-white, 34.

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? In regards to the above, part of my motivation for going so sex-crazy this week was greediness. I also feel like I’m in an incredibly lucky position for some reason and should take advantage of the fact that there are all these women that want to be with me. Another factor is that I think I may be coming to an end of promiscuous sex due to my feelings for my Tuesday partner. My slutty days may be passing me by.

What do you think about the Casual Sex Project? I read it a lot. It’s entertaining and revealing and helps me sort out my own motivations and journey.

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