Through high school I had done what most of us do, take what I could get. Oral sex seemed to be a one-way street where I gave it, they tried it, and then told me to just fuck them. The fucking was missionary, them on top, or doggy style as the big finishing move. I was much more open than anyone I was ever with. Me and Ann had sex on the couch once. It was as you would expect, missionary.
This was college. I was lucky enough to live in a large house, with fairly liberal roommates. There was a hot tub in a Gazebo. We lit it with Christmas lights, just the white ones. It was nice enough. The house was out of the way, fairly private, and the usual for parties.
I met Rose on Yahoo Chat. I miss the local section of that chat room. I could chat anonymously with locals. I could private chat, and talk dirty. I met some really fun people in person from the rooms. Rose was the high bar of those.
She was two years older than I was, and had a lot more sexual experience. Things like trying anal, or watching porn and having sex at the same time seemed like bucket list items to me. They were fun to her. She was comfortable. She knew what she was doing. She had done a lot of it before.
Rose was 5’10”. Brown hair. B cup breasts with perfect nipples, but her ass was the star of the show. It formed a heart when she bent over. Her pussy would swell, and she was usually very wet. Speaking of her pussy, it was delicious. She was the first one to ever just sit on my face, something I enjoy to this day.
One day she and I were having the “compatibility talk.” Seeing what each other wanted sexually. We were too young to know the other stuff. Monogamous, open, what we wanted to try. This is a conversation I have always repeated. You learn a lot. I know that I need a certain type to keep me entertained.
Her stuff was easy. Toys. Blindfolds. Handcuffs. Her big thing was that she wanted me to learn to make her squirt. She could do it herself, but no guy had. Easy enough. I always fear the conversation from my side. How do you tell someone that their being spit roasted would be OK. If they wanted to fuck your best friend it is a plus? That you enjoy fucking women in serious relationships.
I started easy, told her that I would love any number of group scenarios. Also, would love to try anal. She chuckled, and asked if that was it. I told her it was. She chuckled, and dropped her pants. “Anal is easy, we need friends for the rest…” Dick instantly hard, throbbing.
I remember getting it in to this day. She puta condom on me, then pulled it off. Lightly coating me in it. She took the condom over her finger, rubbed her ass, then slowly put it in, and pulled it out. “ready, I will lead. You don’t need to just ram that in there…”
My dick is just above normal. Nice head, decent length. I always thought of myself as small. My best friend has a huge dick, and that is really all I had to compare mine to. I knew he was big, but I had no idea being thinner and two inches shorter was good for most women. He is actually just glad when one can take him.
She got on all fours, and guided me in. My favorite feeling is entering for the first time. This time is seared into my mind. A little pressure. I wondered if it would happen as I felt the tiniest pinhole of an opening start. She exhaled, and took me in a little at a time. Just the tip. Pause. Breath. Sliding in another inch. Out a bit, pause, breath, in a little more until it was all the way. I slowly pumped until I was done.
A few weeks later we had some friends over. Brandon was my best friend, Jenn was his eventual wife, and someone I always wanted. She was actually like one of the guys. Cool. We liked her. She could wing man, or talk, hang out, whatever. I was very close with her. Them dating made us all closer.
The night went as usual. Dinner. Hanging out. Movie. Drinking. Hot tub. Brandon forgot their suits. What a dumb fuck.
After a quick debate, we all decided skinny was what was happening. We grabbed full drinks, and departed for the Gazebo. I always had to go first. Take off the top cover keeping the heat in, and all that. This worked to my advantage. Brandon always just stepped over the side. Any girls always used the steps. I always grabbed the lay down spot near the steps. Most jets, best view of them getting in, and jet control.
Tonight, that view was naked. Rose got in, and told me to take a look as Jenn got in. Jen leaned way over making eye contact. Her large breasts hung nicely. She put one leg in, then stood up looking down at me. She said, “what have I done” as she turned around, bent over, and gave me the rear end view of my life. She then just fell forward into her somewhat usual seat in the corner. Brandon got in from the side with minimal incident. He was very drunk.
Rose told me she wanted me to sit on the side. I was a little warm, so I did. She started playing with my dick. Jenn bit her lip. Brandon said OK, and pulled Jenn close. Same room was a fantasy. This was happening.
Rose took me down her throat. Rose gave amazing head. One of the few people I enjoyed it from was her. She slowly raised her hips from the water facing Brandon. Jenn was very sexy, but Rose won the ass department. After a few minutes, I reached back to feel her gorged pussy. This thing was super wet. Dripping.
Jenn had mounted Brandon’s giant cock. I remember watching her position herself high in the water, move a hand down, and slowly sink down. It took about a minute. Once it was in she looked like it was OK, but painful. He looked like he didn’t want to hurt her. I remember Brandon being fixated on Rose’s ass and pussy. She was showing him what I had. I knew it. I loved it.
Rose looked up and asked if I was ready to put on a show. Of fucking course I was. This was my moment. I stood positioning myself behind her swollen, throbbing wet pussy, and guided myself in. She was so wet. It felt like we were using lube. There was no easing in, no slow going. I inserted until I was fully in, and started fucking.
Brandon was just watching at this point. I remember him asking Jenn if he could blow inside her, and her saying no. There was a small, hushed discussion I couldn’t hear, then “Ah, OK…UNNGGGHHH!!!” from him. At this point, He was watching. So was she.
Rose came hard. Her pussy tightened around my cock, and she asked if she was to wet. I learned always say yes to this, because it always leads to anal. She told me to fuck her ass. I had never heard it like that before. She was putting on a show. I remember her saying “for the record, a dick his size will never get my ass” as she pointed at Brandon.
For the first time in my life I was sexually superior to Brandon. I had lasted longer. Not only that, but he was watching me, and Jenn was looking like She was ready for a turn. My smaller dick got anal, his didn’t. His girl wouldn’t even take his cum.
I aligned my head with her asshole. It was pretty well lubed from how wet she was. I rubbed my hand from her pussy to her asshole, it was more than wet enough to spare the necessary lube. As I applied pressure I remember Rose shifting her hips right. I remember wondering what just happened. Did I hurt her? I pulled back a bit.
She leveled her hips. Moved a hand back to her ass cheek, pulling at it. Pushing back on me, and shifting her hips left. I felt her ass open. Left, right, left, right, lef6t, right, then I found myself fully hilted in her ass. “I said fuck my ass” she said. I knew only to start pounding as hard as I could.
I came soon after that. Sitting in the tub she looked pleased. Brandon got out, saying to “carry on” and that he had the spins. Jenn sat for a minute. Rose got out to check on Dan. I remember sitting there with Jenn. I wanted her next. I wanted to cum in every last crevice she could offer, just to come back and use my cum as lube for a second time. I wanted to fuck her like he couldn’t.
She slid over, adjusting the jets to off. Her breast hit my hard cock. She asked what we should do about it…but then I heard Rose. He is sick, where are the blankets…Fuck.
She insisted I get out first. I stood. There was this moment where my hard cock was inches from her face. She smiled, and looked at it, then me. She said she had an idea of how to start with that. Her face said feed me your cock…my conscious said get blankets and a trash can for Brandon.
It later turned out a group sex night had been planned by Rose. Brandon liked fucking drunk, and wanted to be too drunk. Brandon later told me he wished I fucked her, because she kind of held it against him that I hadn’t.
More will follow in later stories.