Fucking shit, I thought about having sex with three girls today and I haven’t thought about screwing my girlfriend once. Not that the sex isn’t good, it’s great. She loves when I hold her down and I love it when I take her from behind. She wants to try pegging me, and I want to try anal on her, so we’re on our way to a compromise. The sex is fantastic. And frequent. Just not lately, she’s been in Mexico for a week, and will be for three more, and I haven’t jacked off in that time. Once we started getting sexy over text but then she pulled the “you only want sex card” and I had to back off like crazy. My dick gets hard at even the sight of a girl.
First girl I wanted to fuck was my ex-girlfriend. Last summer we were a thing. She housesat this house for a whole month, so we got up to whatever we wanted in there. Which wasn’t much – I got a hand up her shirt early on, but the second I went down south she froze up. Her ass became on-limits before her vagina, so I felt her ass up lower and lower until I touched the outer lips and then boom, nothing more that night, pack your shit and go home. Within the month I was eating her out.
We had sex in the end, if you can call it that. Her plane came in 32 minutes and she wanted half an hour of buffer time. We were both buck-ass naked on my bed, she was bent over texting and I was behind her. I grabbed one of her ass-cheeks in my hand. “God I wish I could fuck you,” I said, but she was a religious girl, and I knew it wouldn’t be allowed. She turned away from her phone a moment to look at me.
“You have two minutes.”
Alright, this is where the problems started. I’m not particularly well-gifted or anything. Hell, I’m happy I’ve got what I do, I’m only 5’7″ (5’8″ on a good day). So I’m crazy excited, she’s moving across the country today and we’ve already agreed this is going to be it for our relationship, so I stick it in immediately.
Or try to, at least. She’s such a tiny girl. I barely get the head in. It’s not like she’s not wet – she’s been dripping over my mouth and fingers for the past hour. She is legitimately that small. I keep trying, only making a little headway, when she tells me to get on my back. She climbs over me and slips herself on, slowly, and starts riding, this look on her face like she’s either in the most pain of her life or having the most intense experience.
A little background before I finish this part of the story. I’m not a virgin, I’ve been with two girls before this – only once each, though. One-night stands are great and all, but not if you want practice. I have no idea how to have sex. And the girl on my dick right now is a virgin so she has no idea. She’s doing what feels good for her. An issue is that I’ve never cum before – every time I’ve had sex I’ve made the girl cum a few times and then we fall asleep together, exhausted.
So this girl is riding me, unprotected, and she starts moaning, she’s loving it, even if her tiny body is filled to capacity. Something’s up with me though, I barely care that she’s there. I can feel myself getting more and more limp inside of her.
“Oh shit, I’m about to cum,” I yell, and she scrambles off, and I give her a kiss and take her to the airport. About a month after we break up she starts playing the pregnancy scare card and I’m having none of it. She gets her period a week later and admits she was just worrying.
Anyway, we dated last summer, and her having a house all to herself was amazing. We got up to so much in there. Incrementally, which made it better. So now, being home for the summer, going on bike rides back by where she used to live, I start getting nostalgic for her body and think about fucking her again. That was the first of three.
The next was a little more dangerous. We got coffee earlier today in order for her to be less pissed at me. This one is also going to take a bit of backstory.
Coffee girl is the one who took my virginity. She’s also my girlfriend’s best friend. After I slept with coffee girl things were weird with all three of us. Eventually I ended things with coffee girl, she was unhappy, came to visit all of us anyway, I fucked another girl, things got worse. Coffee girl always hated my guts.
Anyway, so I start dating my girlfriend over a year later, and it’s driving coffee girl nuts. She can’t stand me, and she can’t stand her best friend being with me. The two of them go at it over and over again. I stay out of it as best I can. Last week, I get a message from coffee girl asking to get coffee and bury the hatchet.
She’s half an hour late. Not that I mind, I’ve got a shitload of New Yorkers to catch up on so I sit in the coffee shop reading and drinking my iced coffee when she comes in.
First off, she’s very alt. Short hair, half of it dyed blue. Ring through the middle of her nose – I know there’s a word for it, starts with a T – three studs around her nostrils, baggy tank top and barely-shaven armpits. So much skin showing, and I can remember it sweaty. She’s dyed her hair so much it’s in fucking terrible condition, hard and crinkly, good for gripping when you’re pounding into her. God I missed that.
Last time we talked it was a three-hour hate session against me followed by an hour of catching up. This time she comes in friendly, everything is pleasant, she tells me about her art and her mom and her job and her education. We talk about my current girlfriend and she tells me how bad it’s been, and I’m thinking of bending her over the coffeeshop table while I explain to her how important it is for her and my girlfriend to get along. Things end well. She gets up and I admire her ass for a second, knowing I cannot be caught under any circumstances. She sways off.
I text my girlfriend. “How are you doing baby?” There’s no reply for almost fifteen minutes. Then she responds but I wait until I’m at a red light to pick it up. I read it, and it’s her talking about what she bought at the shops, and how her family is doing, and she asks about my day. I tell her everything but the coffee date – neither of us want her to know until she gets back.
My girlfriend is the first – and only – girl who has ever got me to cum. For the first month I never had an orgasm, so we didn’t bother using condoms. I got her off a number of times each night. But then one time it was feeling incredible, so I slipped one on. I told her to roll onto her back. I pressed her shoulders to the bed and she lifted her ass to me. I slipped inside her and leaned forward, grabbing her neck and choking her. She’s always loved that. I started going at it, harder than I ever have before, and then I cursed, and then I felt the cum rising in my balls and then I felt myself emptying into the condom inside of her, thrusting again and again until there was nothing left in my body and I fell onto the bed, panting. It was a full minute before I spoke again.
I’ve still only ever gotten off by taking her from behind. I was close once in the missionary position, but the she wanted me to fuck her from behind and I said okay. Back at school we have sex four times a week. It’s been eight days since the last time and I’m feeling it.
She says she’s going out to dinner and won’t be able to text again for a while. Fuck time zones. I tell her alright and I miss her, but not I love you, because we’re not there yet. Maybe by the end of the summer.
I’ve got this friend, her name is Brandy but we call her Caroline, who I sort of knew in high school. For whatever reason we got really close once we were in college and see each other every time we’re home on break. We had a number of sweet moments in the botanical gardens and on bridges at midnight. We made out once, before I had even lost my virginity, but nothing since. Even though I kept offering.
I’ve talked her through break-ups and picked her up when her mom becomes too much. We know almost everything about each other, even if we only talk every other month, and god do I want to fuck her. She’s got these strong thighs and skinny waist, way too much lipstick and big eyes. She’s a good kisser. Not afraid to use her teeth, and knowledgeable enough to know how and when they should be employed. Her skin is the softest I’ve ever touched. I’ve dreamt so many times of burying myself inside of her and just running my hands over her skin while I fuck her blind.
Of course, she’s always said no. And now I can’t because I’m in a relationship. Probably can’t. Shouldn’t is the most accurate. Anyway, I’m seeing her tonight, and it’ll be good to catch up…