My First Sleepover

I had been arranging plans to meet Bradley (not Brad!) for a few days now. We met on Bumble. I actually like Bumble a bit more than Tinder, but we won’t get into that now. I was a bit scared that Alex might stalk me or something after last night, but that never happened, I actually didn’t get any texts from him.

I got off work at 5, went home and showered, shaved, and did my hair. We were meeting at a restaurant that both of us wanted to try but had never been. I took an Uber because I really didn’t want to risk driving buzzed again. Over dinner, we had some really nice conversations. Minus the fact that I called him “Brad” at the beginning and he had to sternly correct me to “Bradley,” we seemed to agree on everything. We had each had a glass of wine before our meal arrived, and then had ordered a second one once the meal came out.

He was in a similar situation to me: he had kids, was divorced, but he was actually looking for a relationship. We had briefly discussed this over text, but I really wanted to make it clear that I’m just in it for one day at a time, and that given I’m only a few months out of a 20+ year relationship, that I am pretty well against any kind of follow on.

He had told me early on in our text conversations that I should probably stick to Tinder for these kinds of meetups, but he wanted to see me anyway, so I think things were pretty clear that we were just in this for the night.

After we finished, he invited me back to his place for dessert. I thought that was a little unique, considering most the time I thought people went back for “drinks”. I agreed. We grabbed an Uber to his place, and we got there I asked what was for dessert. “Me,” he joked, and then got out a tub of Ben & Jerry’s Cherry Garcia. Clever, he had asked me what my favorite ice cream was a few days back. Bonus points for sure.

He brought out two spoons and we sat on the couch taking turns shoveling it into our mouths. After some conversation, he sat the mostly eaten tub to the side and crawled up over me and we started kissing. His kisses were more passionate and slow than the previous men I had been with. Bradley was in his mid 30’s, where the others have been a decade younger.

It was at this point that I realized we were absolutely going to be fooling around, and I had just made a post on Reddit the other day about my first hookup cumming in my mouth. The post really scared some reality into me in that I was terrified of catching something from him by giving him a blowjob. I asked him when the last time he had been tested was, under the impression based on my Reddit post that this was a totally normal question, and he chuckled, saying he didn’t really remember, maybe 9 months ago or so.

I shook my head, and he asked if it was okay. I didn’t know what to do because I hadn’t been in this boat before, but he said we could stop if I wasn’t ready. He was being really nice. I smiled and told him everything was great. I took this moment to stand up and slowly unbutton my shirt, staring him in the eyes the whole time. He just sat and watched. I slid down my blouse and then unclamped my bra, letting it fall to the floor.

“I have protection in my room,” he told me, which made me feel good with my nervousness more than likely showing through. I smiled and nodded, and he stood up, grabbed my hand, and then walked me into his room. He opened his drawer, grabbed a condom, and sat it on top, then started taking off his clothes.

He told me he doesn’t do this often, so he’s not really sure what we’re supposed to do, and I told him that I was the same. I unbuttoned my pants and slid everything off, and awkwardly stood there completely naked while he finished getting undressed. He looked up at me and let out a “holy shit” which made me blush and I said “I thought the same thing when I saw you.”

This was a bit of a lie. He didn’t have the absolutely perfect body I’d seen before, but he was still very sexy. He had a hairy chest and stomach, he had a very typical dad-bod and there’s nothing wrong with that. I thought it was kind of funny considering how hairy he was in the fact that he had completely shaven everything around his crotch.

He walked up to me and kissed me again, pressing up against me. His cock was still completely soft, and I reached down and gave it a grab. He slowly pushed his weight against me, knocking me back onto the bed. He immediately got down on his knees and started kissing the inside of my legs, starting with my knees, moving across from knee to knee, then up a little closer, until he arrived up at my pussy (I never know what word to use here. I hate that books use either “folds” or “sex” most of the time. It’s not sex unless you’re having sex!). I think the anticipation felt much better than the actual act of him licking me, but it still felt good.

He went down on me for a little while, mostly focusing slow, long licks between my clit and my hole. He definitely had experience, he knew what to do and it showed. Still, while I was getting licked, I was thinking about what was going to be next. Was he going to fuck me, or was I going to give him a blowjob? I still was nervous about the risks, that Reddit post really freaked me out.

I hadn’t noticed that at some point he must have grabbed the condom, opened it, and put it on while he was going down on me, but he climbed up on me and slowly slid it in. I was mortified. I asked him where the condom was, and he said not to worry, he’s wearing it, and I looked down to see he was telling the truth. I relaxed a bit, and he started thrusting.

It wasn’t but two minutes later that he said he was getting close, and I said I wanted him to cum on my chest. I think the thought of this set him over the edge, because he instantly came in the condom. Watching his face with the grunts almost made me laugh. His face was red and the veins in his neck pronounced. He looked like a guy I have seen doing dead lifts at the gym.

He rolled over onto his back, completely out of breath, and he pulled the condom off and dropped it in the trash, before looking over at me. He told me it was incredible, and I told a little fib and told him I agreed. He stretched his arm out, basically hinting that I should lay on his shoulder, so I took his lead and did so.

He said again how hot it was, and I reached down and grabbed his cock with a very soft grip and started stroking it. I said I agreed, but I didn’t get a chance to do my thing, and he let me play with him by stroking him for a few minutes before he said he couldn’t take it anymore, so I stopped.

It was getting late, and I told him that I had a blast, but I needed to go. He asked me to stay the night. I told him I had to work the next day so I should probably go, and he said he had to be at work around 9, so if I stayed he could drop me wherever I needed. I didn’t need to work until 11, so it wasn’t a terrible idea and I don’t know why, but I agreed. I told him I needed to use the bathroom, and while I was in there I was thinking of excuses to leave, and by the time I came back, he was completely passed out.

I decided that would be a completely asshole thing to do, so I crawled in next to him and fell asleep pretty quickly myself.

I woke up at 6:30, the sun somehow was peering through a crack in the blinds, directly in my eyes. I rolled over and saw that he was completely uncovered, laying out almost like a starfish, completely naked, morning wood in full view. I must have hogged all the blankets. My ex used to always complain about this. 

This gave me a great idea. I slid off the bed and he didn’t budge. I walked around to the foot and as slowly as I could, crept up and slid my mouth over his cock. I slowly started sucking, wondering when he was going to wake up.

It wasn’t even a minute later when he opened his eyes and registered what was happening. I immediately asked him if this was okay, and he enthusiastically agreed. I started sucking a bit faster and with more force, and then the thought of catching something reared in my head, so I leaned back, straddling over the top of his legs, with his cock right near my crotch. 

After I moved, I came back with a bit more motion, and he asked if we could use some lube, since he never does anything dry. I agreed, and he reached up and grabbed a bottle of coconut oil from his side table and handed it to me. I squirted a little in my hands, rubbed them together, and started stroking him again. I started slowly, covering every bit of his shaft. His cock wasn’t quite big enough to stroke with both hands, so I played with his balls a little with my left hand and stroked with my right. 

Soon after, he started moaning very loudly and his cock started pulsing. I could tell he was very close. I grabbed with both hands and started twisting in opposite directions and he almost instantly came. I pointed it up toward his belly button, and his cum started catching in his hair. I kept stroking, slowing my motion, until he was done, and I realized this was my first post-marriage handjob. I had given my ex handjobs here and there, but it was always laying next to him. I hadn’t ever sat there this exposed, and I certainly hadn’t really ever watched everything unfold like this. It was incredibly hot, and it made me want to do it again, and soon. 

He looked down at his stomach and laughed at the mess. I laughed with him. He said he needed to rinse off before we head out, but that I should make us both some coffee if I drank it. I threw on one of his shirts and went out there to figure it out. I made the coffee no problem, and he came walking out wearing his pants but no shirt. He made a joke about how his stomach was clean now and it made me blush a little.

I told him the coffee was about done brewing and I walked over to the living room and grabbed my shirt from the floor. He was watching me and said something about how he wishes I hadn’t been so careful bending over. It took me a second to register that I even had been careful not to just moon him and I chuckled a bit.

We drank our coffee and then I went and got dressed. He told me he had to brush his teeth, and I think it was one last excuse to watch me change, because he didn’t really pay much attention to his teeth.

He asked me where he should drop me off, and I told him where I lived. He kind of looked disappointed and I gave him a questioning look, and he said it was the complete opposite direction of his office. I told him it was fine, I could take an Uber, and he told me it was fine, he could be a little late.

I insisted and called the Uber, he felt bad and tried to hand me some money to cover it. I declined. The Uber arrived and took me home, and I took my own shower and got ready for work.