First Time with Long-Time Crush

by Blonde

What’s your gender? Woman
How old are you? 22
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: Some college (currently in college)
What’s your current relationship status? Dating casually
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Adventurous, Mostly Submissive, Horny, Nonmonogamous
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 2

First Time with Long-Time Crush

How long ago did this hookup happen? A little over a week

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? D is 25, cute with a nice smile, mixed, and is a few inches taller than me – about 5’11. He’s got nice, broad shoulders, is lean and kisses me in a way that makes me melt. I’ve known him for a few years, but we’ve been more like acquaintances until recently. When we met, it was through my then-boyfriend. As D was dating someone at the time as well, I couldn’t pursue him. From the moment we met, I knew we had some kind of connection. He’s one of those rare people you meet in life with whom you have an almost palpable connection (so, needless to say, I’ve waited for him to be single for a while). He recently contacted the company I work for (without knowing I work there), and one of my coworkers met him. I hadn’t seen him in a year or so at this point. I grilled her for information when I saw his name in our system, and her answers confirmed he was who I thought. We had never exchanged any contact info, but I quickly found him on Instagram and slid in his DMs – my first ever DM slide! He responded, and the conversation led to an exchange of phone numbers and dinner plans for the next night. We met at the restaurant and he was cuter than I remember since he’s a few years older now. After dinner, drinks, and talking, the night ended with a make-out session, of course. He also rubbed my dripping pussy and grabbed one of my breasts. This story is about our next date, which was a very long, sexually tense 7 days after that first date. We sexted a bit during the week and exchanged pictures, but no nudes. We talked about things we’re into; we had a good bit of things in common.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He arrived at my house that night, and we quickly left to do a little bit of shopping and get ingredients for dinner since we’d planned to cook. We started cooking when we got back to the house, not really doing anything sexual other than standing near each other and touching innocently. By the time we finished dinner and cleaned up, it was pretty late. I was a bit sleepy, but I’ll often prioritize sex, and our sexting conversations led me to believe he’d be worth it. I was sitting at the bar in the kitchen when he came over to kiss me. Then we went to my room and changed. Being the tease I am, I asked him if he thought he deserved a surprise. Of course, he said yes, so I told him to cover his eyes as I left the room. I came back in wearing a navy blue sheer bodysuit with lace details that left little to the imagination. A previous partner once told me it shows off my hips in a way that reminded him of Kim K. He said something like “wow” with a surprised expression, and I lied down next to him on the bed with my ass slightly in the air. He rolled me over and started to kiss me, working his way down. He began to give me head, and I was disappointed that it fell short of my expectations. I’d previously told him I’m very vocal in bed, so when I hadn’t made a sound after about a minute and a half, he stopped and asked what he needed to do to make me feel good – which is a turn-on by itself! That’s the first time a guy has been considerate enough to realize it’s not working and try to fix it. So I guided him for a bit, touching myself while he watched closely. I got out my vibrator because that’s what really gets me off. This lasted for about 10 minutes before we decided to fuck.

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? Before we started, I told him that I’m naturally very tight and that he needed to start slow so that he wouldn’t hurt me, but I guess he was just so excited he didn’t quite do that. We started in missionary and then switched to doggy. After a few minutes, we stopped, and I went to the restroom because I knew he’d torn me. I came back and told him, and he was upset with himself that he had hurt me. I said it was normal (unfortunately) and teased that he should’ve listened when I told him to start slow. I lied down next to him and started using my vibrator while he kissed and choked me, licked and sucked my nipples, and ran his hands over my legs. A few minutes passed, and I had an orgasm while we kissed, moaning into his mouth and bucking my hips as those blissful waves washed over me. I have a really difficult time coming with a partner, so I was very impressed with myself that I was able to with him! After I came, I went down on him (the first time I’d given him head), and he came after a few minutes, complimenting my skills in between strokes. I swallowed all of it that hadn’t escaped my mouth and kept sucking (because I love to be a tease) until he quite literally forced me off of him. We took a shower together and got ready for bed. I got into bed naked, and we naturally both ended up horny again. It was probably a solid hour of us teasing each other before we went to sleep.

It was better overall the next morning. After yoga and lunch, we showered and he was just about to leave to go to work when we started making out on the bed again. I tried many times to stop him because I didn’t want him to be late for work, but my attempts were unsuccessful. I’ll admit I was soaked and definitely horny, so I finally agreed to a quickie. He went down on me for a couple of minutes to put what he’d learned into action, and it was definitely better. He fucked me missionary, starting off incredibly slow – I’m talking millimeter by millimeter pace – and I told him to go faster when I was ready. He only lasted a few minutes and then came on my stomach. We got right back in the shower to quickly rinse off before he headed off to work. I didn’t come and he left me dripping wet, so I had to rub one out later in the day thinking about him choking me and kissing me hard.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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 like him and plan to continue seeing him. Right now we’re something like FWB, but honestly, I wouldn’t hate it if it turned into something a little more serious (open, of course).

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, I was feeling lonely

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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 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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? A close guy friend and my aunt. My friend was excited that I got to finally hook up with a crush.

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? Finally getting to have sex with a crush and someone I vibe with.

What was the WORST thing about this hookup? I was hoping he’d be above-average in size and width, but he’s right at average.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It makes me wonder which nonmonogamous arrangement is best for me right now. I generally tend to avoid the development of feelings, but I’m liking him more and more.

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

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

Anything else you want to add about this hookup? It was a good experience. We’ve had dinner and some make-out sessions (that often lead to him rubbing my pussy) since he stayed over but haven’t been able to have sex because of our current living arrangements. We vibe nicely and he’s easy to get along with. We actually have plans to go out of town this Friday night; I’m excited!

He stayed the night which is unusual for me; I never stay the night nor let anyone stay over, partly because I don’t sleep well with other people. I knew we would finish really late, though, and he lives 45 minutes away from me, so I didn’t want him to be driving home late. I also wanted him to come to the yoga class I attend on Saturdays and make pancakes. I was sleeping pretty decently actually until the dog woke me up early in the morning. I tried to occupy myself outside my room for about half an hour but ended up waking him as well. We cooked pancakes before heading off to yoga.

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? Casual sex is great. I wish society was more receptive to the idea of it.

What do you think about the Casual Sex Project? It’s great! I like reading other stories and having the ability to submit mine.

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