First time bareback [TransF / CisF] | 2016

So, this is a story of me and my ex. Let's call her Pink, because why not. We met when we started working together, I was only 21 and awkward and nerdy, she was 28 and basically a sex goddess in my eyes. She stood out immediately, a bright pink pixie cut, some nice tattoos, and the most amazing ass I have ever seen. It was, honestly, God's greatest creation. She had wide hips, a full round butt, and she would swing her hips back and forth as she walked around in either tight pants(well, with her waist to hip ratio, any pants became tight) or a dress that hugged her curves. She was 5'6" or so and the rest of her was curvy, she had great handful-sized breasts, basically I could not keep my eyes off her.

I'm 6'3"(yes, I know, very tall) with small breasts and very long dark hair. My butt is my best feature, I'd say, but nowhere close to hers. There's a few old Gonewild albums in my history, for the curious.

I still remember all the times we spent flirting at work, from just putting music on for eachother and random discussions(it was a small place, we often had a good amount of privacy) all the way up to one time we had a swordfight with mops and chairs in the middle of a shift. To be honest I wasn't terribly experienced, especially with girls, and I kind of acted like a little kid with a crush around her. I teased her, poked her, anything to get her attention. Somehow she wound up liking me too, and we started hooking up. She was the first girl I ever had sex with. We liked to try new things, a LOT of new things, so I have a lot of memorable stories if there's further interest...

Anyway. The actual sexy part begins here. This is the story of the first time we wound up skipping a condom. It started, like normal, with her bicycling over to my place early in the day. A lot of the time we only managed to find time to meet up once every couple weeks, but we got to tease each other at work constantly, finding time to kiss or just bend over and show off for eachother. Additionally, this was right after one roommate got a job, so we finally had the whole place to ourselves instead of having to stick to my bedroom. So we were both quite worked up and excited to begin with. I was wearing jeans and my very tightest t-shirt, nothing else. She strolled up to the door wearing my favorite dress of hers, a tight brown thing that came down to mid-thigh. I think at this point her hair was a somewhat purplish red.

Immediately we were kissing eachother deeply, with a lot of lip biting and pawing at eachother. She knows I love her ass, and that's usually where my hands wind up. I squeezed through the fabric, bending her over backwards I was kissing her so hard, and she was stroking my neck with her other hand gripping my back. My hand slid up under her dress as she started squeezing my butt in return, and I realized she had bicycled the whole way over in a short dress with no panties. I could feel the heat coming off her and knew she was very turned on, and I'm sure she could feel something when we pressed together as well.

Eventually we managed to break contact and head upstairs, away from the street-facing windows. She pushed me down onto the couch and straddled my lap, grinding against me and pinning my hands down. We breathed heavily against eachother and then she bit my neck, a major weak point for me. I let out a squeak followed by a loud moan and gripped the back of her head, arching my back and shoving our breasts together.

I groaned about the frustrating amount of clothing, and she leaned back so we could strip each other's shirts off. Then I undid my pants and she managed to pull them off. She wrapped her arms around me and pushed her body against mine, with the only thing between us being my underwear. She resumed grinding and we both moaned, our crotches rubbing together in all kinds of fun ways.

One note about anatomy... I have a penis. I prefer to consider it a big clit. Honestly, I'm not usually comfortable with having it stimulated, but Pink was a big exception.

So my clit was grinding against her pussy with thin fabric between the two. I would push her down a little and rub my clit against hers, then she would slide up and press my head against her vaginal opening, letting me feel the heat inside her. She was squeezing my breasts, I was grabbing her ass, we wanted each other bad. We were moaning into each other's mouths, when we weren't leaving bite marks in each other's necks. It's a game we often played, grinding together and daring the other to lose control first.

I could feel myself getting too worked up to resist but I wanted to drive her even more crazy first. I pushed her off of me, onto the couch, and slid onto my knees in front of her. One of my hands went to her breast and started kneading it and rubbing her nipple. The other spread her knees apart and stroked her inner thigh, my thumb teasing her slit. I started out kissing her neck, then moved down to her other nipple, licking and gently biting. This nipple had a barbell through it that I loved playing with, tugging, gently twisting, etc. She was moaning and arching her back as I finished with her breast and kissed my way down her stomach.

I nibbled the soft, delicious flesh around her inner thigh. The smell of her was driving me wild, but I love teasing. I nipped at the nook where her thigh met her crotch, then did the same to the other side, before slowly running my tongue between her lips and up to the top of her pussy. I teased her clit with slow licks and a fingertip tantalizingly pushed inside her, working its way all the way into her hot wetness as she bucked and gripped my hair. I lapped at her clit with the tip of my tongue and fingerfucked her for a couple minutes before she suddenly pushed me off and onto my back on the floor.

Instantly she was on top of me, straddling me and tugging my underwear off. She sank her teeth into my neck, making me writhe against the floor and cry out, as her wet lips rubbed against the underside of my clit. She wanted to get me back for all the teasing, and she knew this would drive me wild. She ground her bare pussy against me, both of us gasping in pleasure and hunger, never letting me inside her but running my head and shaft from just above her hole up to her clit. She was rough, shoving her hips against mine, and it would have hurt if she wasn't positively soaking wet. It felt fucking amazing. She rubbed my neck and worked my clit harder and harder, getting just as overstimulated from it as I was.

At this point, we both needed to be fucking right that very second. The only problem was, the condoms were in the next room and getting them would require separating my crotch from hers. So we continued grinding, getting more and more desperate, harder and wetter, harder and wetter.

Eventually, we went a little too far on the downstroke, and we both felt something slip. I was instantly buried two inches inside her hot, wet pussy. We'd never done it without a condom, and we both instantly froze in place. We stared into each other's eyes in shock, as our continued heavy breathing and the throbbing of our crotches gave me one of the most amazing feelings I'd ever had. We sat there for about a minute, just mouthing things like "oh my god" to eachother, trying to muster the willpower to separate.

I could see it in her eyes as all the resistance melted away and she started sliding further down, pulling me deeper in. I threw my head back and inhaled sharply, digging my fingertips into her hips. She bounced on top of me a few times, and it was the most amazing thing, being able to feel just how hot her pussy was and every single ridge inside of her. I couldn't even catch my breath to cry out her name.

Then, just like that, she stopped. She paused for a moment and then tried to pull off of me, but I had lost all my willpower. I grabbed onto her hips, hard, and pulled her back down as I thrusted up, burying all 6.5 inches of my clit inside her. Now it was her turn to throw her head back and cry out my name. We lost all control, her riding me, me thrusting up into her, fucking fast and hard. We had never had sex like this before. We were grabbing desperately to eachother, holding on to whatever we could, thrusting like animals.

Eventually she got frustrated with the position we were in(she can't cum when she's on top) and we moved back to the couch. She was on her back with her legs wrapped around my waist, I pinned her hands down and entered her again, fucking her deep and hard. We kissed like mad, and the feeling of friction between us got even more intense as she steadily got tighter. Finally she clamped down and came, hard, and I continued for a little longer before cumming inside her. It was the most intense orgasm I think I've ever had, before or after. We couldn't even move afterwards, just lying there in a sweaty pile breathing and kissing. It was at least five minutes before I managed to flop off of her and we slowly caught our breath, lying naked on that couch.

Anyway. I have a lot of other fond memories, many fun unique experiences. Let me know if you'd like to hear more.