My (M18) first creampie with the hot older woman (F23) [MF]

Jenny was the hot best friend of the girl who lived next door to me growing up. Besides their daughter the neighbors also had a son, Danny, my age who was my close friend. Danny and I hung out all the time both because our personalities meshed and because we lived so close it was convenient. So, it wasn’t surprising that my paths crossed with Jenny pretty often during my formative years. Looking back, I think she was my first crush. Blonde highlighted hair, about 5’8’’ with long toned legs, a tight body with great tits that looked especially great in the push-up bras and low-cut tops she would wear often. I remember it like it was yesterday when Danny and I shared a hot tub with Jenny and his sister at their family lake house. I beat off to the image for a solid year after the seeing that.

Now my current self would have hit on her, but at the time I was 5 years younger than her and while I did fine with woman my own age, Jenny was in a different league. She wasn’t making out in closets anymore; she was “hooking up” and that was far more intimidating than I could imagine. I knew she thought I was cute because she would tease me about it and ask if I was dating anyone every chance she got and enjoyed my complexion turning as red as the sun when she did. I even overheard her tell Danny’s sister when she didn’t think I was around, “I’m serious, he’s borderline hot now and he’s going to be so hot in a couple years.” The both giggled and I immediately went and told Danny what I heard, which was responded with “You’re making that up.”

Jenny went off to Vanderbilt, Danny and I went off to her former high school and time went by with us only seeing each other here and there over her summer vacations. The summer before Danny and I went to college we headed up to his family lake house to golf and take out the boat for the weekend. His parents were trusting us to go up alone which was perfect since we didn’t have to worry about hiding beer from them, just finding it. On the way up Danny got a call from his sister that asked if we would mind if she crashed the lake house with a few girlfriends. Of course, we didn’t mind, adding woman to the party is never a bad thing and at a minimum our beer problem was solved since they were all around 23.

Danny and I beat the girls up the lake house and were swimming off the dock when we saw his sister’s car pull up with three other girls in it. I hadn’t thought of it until that moment but there was Jenny getting out of the front seat and she looked even hotter than I remember. She looked more adult than student with a more mature body. She had her hair pulled back in a ponytail, piercing blue eyes, full lips and had an unzipped sweater on over her orange take top with her bra or bikini straps easily detectable and short white shorts with flip flops. I jumped out of the water, made a half effort to dry off and went over to the car to help them unload. Danny’s sister wouldn’t let me give her a hug because I was still wet but Jenny did and it was a nice feeling finally being bigger than her and feeling like we were on equal footing opposed to the early days. I introduced myself to the other two girls who I had never met before and then suggested, “I’ll bring in the beer if you’ll share some with us.”

The girls went off to unpack in their rooms and Danny and I moved our stuff down to the basement couches downstairs to give the girls the bedrooms. It was a small house for 6 adults, but being on the water certainly did the trick. Danny and I grabbed a few beers and went back to the lake so the weekend could really begin. After a while the girls came down in their bikinis and laid on the dock drinking and chatting. Jenny stripped into her bikini and I had flashbacks to the last time I saw her at this lake house in a bikini. My memory hadn’t done it justice, she looked phenomenal.

While most of the girls chatted together sporadically including Danny in their stories, Jenny and I were really hitting it off. I asked her about school and post college, she asked me about my athletic scholarship and when I left for school, plus how prom was. I remember thinking in that moment it’s nice to talk to her and not be nervous I’m going to pop a boner or get embarrassed if she flirts with me. She never joined me in the water but she did bring me back a beer every time she went inside to get herself one. We were hitting it off and if I ever had an opportunity, I was going to take it.

After sunset the party moved inside where we transitioned to the girls teaching us some drinking games and playing some old classics that we were already aware of like beer pong. Jenny had covered herself back up in that same orange tank top and shorts over her bikini but even with a little more clothing it was impossible to hide that body. I know I was one of only two eligible guys in the house, but Jenny was openly flirtatious with me and I was now very confident that I was no longer that cute boy from the neighborhood, she was into me. Asking to be my partner during the drinking games, grabbing my bicep, placing a hand on my thigh while she pushed her leg next to mine as we sat on the couch together. My buddy Danny gave me a look of nice work multiple times throughout the night while he struggled to find success with his sisters other two friends.

While the four others went to play a game of beer pong, I went to get another beer to find a nearly empty fridge. I found Jenny right behind me and she said, “no more? We have another case in the fridge downstairs. Come and help me?” I nodded. In that moment a part of me reverted back to my younger self, I was very nervous. I followed her down the stairs and I knew this was the first time I’d ever been alone with her. I was confident she wanted me to make a move but the doubt crept in. Thoughts of “this is Jenny and I’m not that experienced and maybe she was just teasing me for all these years… Ignore the growing boner in your pants she’s too hot and too old for you.”

I had a nervous feeling in the pit of my stomach when we got to the basement, Danny and my bags were covering the two couches we were sleeping on, an old fridge with beer in the corner and a shitty old pool table that must have come with the house towards the end of the room. I was behind her when we reached the bottom of the stairs and she said, “Did you close the door?” I didn’t exactly know what she meant so I answered honestly, “Yeah it closes on its own” and then with one hand she reached back behind her and behind my neck and kissed me softly from behind. We kissed gently before she pulled away and asked, “Is this alright?” My dick was so hard against her ass I think she knew the answer but I said, “Yes” and I kissed her back more deeply this time. Her mouth opened to mine and now I was fully making out with the hot girl I used to fantasize about.

Very quickly my hands were fondling her tits from behind. I had never felt something so incredible to that point in my life. I was cupping them, pushing them up and together, before deciding to reach down the top and inside her bikini with one hand feeling her nipple as our kiss transitioned to me sucking her neck and nibbling on her ear. She took my other hand that wasn’t inside her top and led it down inside her shorts and I started to rub her cleanly shaven pussy, excited and surprised that she was already wet. After she led me down inside her shorts that same hand reached behind her and her fingers slowly traced the outline of my growing shaft through my bathing suit. I tried to keep my focus on fingering her pussy to give her the satisfaction she deserved, but also as to not ruin this incredible moment by blowing too quickly, but it was difficult with those delicate hands teasing my cock.

I knew I had to take a bit of control or else this would be a letdown for us both. I also wanted to show her I knew what I was doing so I pulled my hands out of her top and shorts and turned her around to kiss her face to face for the first time and told her “I’ve thought about you a lot”. Then I bent down and put both of her legs under my right arm and my left arm behind her back and I carried her over to the pool table and put her down on it, loving how her perky tits bounced when she was placed on the table. We kissed more aggressively as she sat on the table and I lowered my face to hers. She gripped my shirt tightly and then helped me strip it off. Then I immediately took off her tank following by her quickly undoing her bikini top for me. She laughed as I said, “Holy Shit” and I buried my face in her tits and began to kiss and suck on her hardening nipples.

She ran her hands through my hair while I tasted her body before pulling my hair up so she could kiss me again. Most of my experience making out to this point in my life had been aggressive and juvenile, but with Jenny she slid her tongue into my lips slowly and fully. It was much sexier that way and then she pushed my head down and I was finally picking up on her cues a bit better. I kissed up her smooth leg as it rested against my chest. She teased my cock with her hand again and I started undoing the buttons on the front of her shorts. Once the buttons were undone, she leaned back onto the table and lifted her ass for me to take the shorts off her. I stood up and looked down at her laying there in only bikini bottoms and her eyes were locked on mine as she teased her clit with her index finger over her bottoms. She wasn’t anything but really turned on and it I still one of the sexiest images I’ve ever seen in my life.

I had to break my trance and lower her bikini bottoms before getting on my knees to go down on her smooth pussy. I had done this with a few women so far in my life but none of Jenny’s caliber or experience. I kept my focus on her, listened to what her body, and her mouth(“Slower…right there, right there”) told me. Her legs were wrapped over my shoulders and my hand rested on her flat stomach before she took my hand and brought it up to her tits. My tongue slid up and down her pussy as one of her hands gripped my hair and the other held mine pushed up against her perky boobs. Her breathing was picking up, but it really picked up when we heard the basement door open with the others wanting more beer. She moaned loudly at that moment, not because of my solid work but because she didn’t want them coming down the stairs. But that louder moan of my name gave me more confidence and I really started going with a better rhythm then and the moans became more frequent and her grip on my hair became stronger. “You’re almost there, Brian, right there…. I’m going to cum, I’m cumming.” I loved the taste of her juices inside my mouth and I loved the feeling of her heels digging into my shoulder blades. I was satisfied, but Jenny wasn’t.

She sat and up after catching her breadth and said “You were good” and pulled me in for another kiss. It was the first time someone had cum on my tongue and tasted themselves from it immediately after. I was with a sexual goddess now and I was going to enjoy every second of this for as long as I possibly could. She must have pulled off her pony tail while I was going down on her because now her long blonde hair was completely undone and she looked even sexier.

She scooted to the corner of the table and she reached behind me to lower my bathing suit to the floor as I stood in front of her completely naked. We kissed again but I could feel both of her hands reach out for my throbbing dick. One hand slowly stroked my shaft while the other hand massaged my balls. She continued working my hard dick as she broke away from our kiss and said, “I like that you still think about me, I always had a crush on you” I kissed her again but she only kissed me back briefly before saying, “Do you want to have sex?”

“Yes, yes I do.” Is what I think I said but it was through a moan, I’m sure. I told her my condoms were in the car and she said she was clean and, on the pill, so we didn’t need one if I didn’t want one. I think I said, “Are you sure?” But in reality, I think we went back to making out and she knew I was in. She smiled and then climbed down from the table and took my hand to lead me over to the couch which we both tossed the bags off of. “Sit down” she told me and I sat down looking up at her as my hands returned to her tits. She straddled me and lined up my hard dick with her pussy using her delicate hand. She looked down on me, my hands gripping her curves and her sexy disheveled blonde hair framing her sexy face through the dimly lit room. “Are you ready?” She asked and I nodded.

She lowered herself onto my shaft and I could feel her wet pussy grip my cock as she lowered herself inch by inch. Her head sprung back to look up towards the ceiling as her tits heaved out and bounced in my face as she began to feel comfortable with my size riding faster and deeper. I used my hands to help with her rhythm but then reached around to grip her ass. My strong hands filled up with each cheek as her eyes returned to mine. I looked at her intensely as I began to thrust up from the couch to get even deeper inside her tight pussy. She was at the same volume that I was grunting. Jenny moaned, “ahhuh, ahhuh” and “mhmm, mhmm” which translated to me as, “Yes, Yes” and “More of this, I like this.” Her mouth was wide open and her eyes were wide, she was getting what she wanted and so was I.

I would like to say this went on for hours and we went all night, but alas that wasn’t in the cards for me especially after she told me, “Stop moving, Brian. Let me ride you” in a soft but sexy tone. I let her take control and she gave me the best ride I had ever experienced by far at that point. My face again buried in her tits before she pushed me back so she could see my face. I told her, “Jenny I’m close. Do you want me to pull out?” She rode my harder, “Do you want to come inside me Brian, you can come inside me. You can come inside me. Cum inside me.” On the second order I blew my load inside Jenny’s tight pussy for the first time and she continued riding me until I was as soft as possible inside her pussy. I had made it and not completely embarrassed myself, in fact I had made this hot older woman cum.

We put ourselves together, made out some more and then went upstairs to find that everyone had gone to bed. I walked her to her room (that she was sharing with another girl), kissed again, and told her how fun that was. She agreed and I’m confident Jenny enjoyed herself because that wouldn’t be the last time we would get together. In fact, we would get together again that weekend. Once I left Jenny to her room, I went to wake up Danny off the floor to come back down and use the couches we were supposed to sleep on. He told me I was a lucky bastard and I had to sleep on the bed I hooked up with her on. I spent the next hour giving him all the details of my first cream pie with his sister’s best friend.

Source: reddit.com/r/gonewildstories/comments/xscepl/my_m18_first_creampie_with_the_hot_older_woman