Author: AllTheBoysIveFckedB4

I told yall I would write about this eventually…
Alright, so I met a guy in my early 20s who was an especially interesting character. Before him, I had been in a series of relationships that were pretty PG and had just gone through a terrible breakup when we were introduced.
We immediately had sexual tension and slept together pretty quickly because that was all either of us wanted at the time. We never had bad sex because the chemistry made it easy. The first couple of times it happened it was VERY good and just felt really natural and fun. I had actually never had a guy get me off multiple times in one session and it was pretty clear he was enjoying himself as well. However, I could tell he was holding back a little and couldn’t quite put my finger on why (no pun intended).
I personally had always been really curious about experimenting in bed, but I was shy and had only dated really religious folks in my youth so I never really wanted to ask for it. If I’m being honest, I wasn’t even sure what to ask for.
After seeing each other for a couple of weeks this guy and I went to dinner and got into a conversation about exes. He mentioned a girlfriend once broke up with him because he was too weird in bed. I made the comment he wasn’t that weird and his eyes darkened a little as he explained I didn’t know him that well. That got my mind whirling.
After dinner, we were heading up to my apartment and he pinned me against the wall in my elevator as we started making out. He had done this a couple of times since we had been seeing each other so this wasn’t particularly remarkable, but this time he got a little more aggressive and ended up full-on picking me up off the floor and carrying me to my apartment while my legs were wrapped around him. The moment we were through the door he took me to bed and started taking off my dress and let me pull off his shirt.
We were going at it a little harder than we had in past sessions. I don’t even know how to explain it, but it was like we were both challenging each other with how aggressive we could get. He bit my lip, so I tugged at his hair. He pinned me down, so I dragged my teeth across his neck. I’m not really sure what possessed me to do this, but finally, I reached up and scratched the fuck out of his back. I’m pretty sure I drew blood. He pulled away and gave me a look that was almost angry but I couldn’t help but notice a hint of a smile as he regarded me carefully.
“What the hell?” He asked as he got up to study his back in my mirror. He was hard to read at the moment but more than anything he just looked amused. Still, I got really embarrassed and couldn’t even stammer out an apology.
“How would you like if I did that to you?” He asked incredulously as I just stared at the ground. “You don’t understand,” he continued, “I’m really asking how you would like it if I did that to you… Or maybe other things.”
I didn’t know what to say, but apparently I started smiling because his face lit up with a wicked grin as he considered me. I think I just gave a little shrug in acceptance and asked what he had in mind.
I swear in less than a second he was across the room and back on top of me. He gently pushed my head to the side and put his mouth to my ear and demanded an apology. Half out of shock and half out of curiosity, I just silent still and shook my head. He grabbed one of my wrists and pinned it to the bed as he pressed my cheek into the pillow and asked if I was sorry. Again, I didn’t respond as he pressed me harder against the mattress. He told me he was going to punish me then so I just gave him a smile and shrug.
He got up immediately and grabbed me by the hand, hoisting me up before I could react. He pulled out the chair from my desk and full-on bent me over his knee as he sat down. He told me to apologize and again I shook my head so he very gently spanked me. He kept demanding it so I verbally refused and told him to fuck off. He spanked me harder. Then he very slowly slid his fingers inside me and moved them in-and-out for a couple of seconds before asking me to apologize again if I wanted him to continue. I hesitated because it felt really good but finally I shook my head so he pulled his fingers out and spanked me harder. This time I gasped as tears sprang to my eyes, but I still stayed silent.
He plunged two fingers inside me once which made me moan, but instead of giving me the chance to enjoy it, he removed his fingers immediately and just let them hover there. This was far more torturous than the spanking. I started whimpering, begging for him to keep going, but every time I tried to move he held me down and kept circling his fingers directly outside of me so that I could feel him but get absolutely no release.
Finally, after about ten seconds of agony, I said I was sorry. He made me repeat it twice before he pulled me up and bent me over the desk and fucked me like that. He pressed my cheek into the wood and told me if I enjoyed it he would stop. Every time I’d let out a moan he would push me harder into the desk and tell me to stop.
It usually takes a bit of time for me to climax like that, but I came in literally twenty seconds with one of the best orgasms of my life. He spanked me again for that, but then came very shortly after.
So interestingly enough he got super self-conscious afterward and kept asking if I was ok. I asked him what else he was into and if we could do it again…
Things get real weird in this story. Buckle up for more parts.

My first girlfriend is a multi-part saga of her own I will write about eventually. I don’t exactly miss her because she was an extraordinarily difficult person to be with, but I definitely miss the sex. She was fucking insatiable and generally open to anything.

Anyway, I was really young when we dated and remarkably less experienced than her in every way but one: I had been with men. She had literally only made out with two men in her life and didn’t think it was her thing. I respected that- to each their own. However, she was also weirdly competitive about these things and hated that I had an experience she couldn’t relate to.

As time went on she started getting curious and kept asking me questions about what it was like. Finally she admitted it was something she would be open to trying once, but with very specific ground rules. She didn’t want vaginal penetration (I can work with that), and it had to be a stranger (guys hit on her a lot and she didn’t want to give anyone in our circle a reason to question her gayness). Read more »