My best friend
One of my best friends for many years was this super quiet nerd guy. We met when we were like 14, and he never had a girlfriend all through high school and such. He could barely talk to girls at all. We went off to college, and he dated a nerd girl for a bit, but she was "saving herself for marriage" or some shit. He told me that the most she would do is give him a weak handy sometimes, in the dark.
Around the same time I started dating this hot ass girl, long brunette hair, pretty with a delicious fat ass. She was a lot of fun and loved sex. We were together a year or so, and his girlfriend and him broke up, and he was super sad. A few months go by and my girl and I were talking about how sad he seemed and she said he probably just needs to get laid. I told her his is probably a virgin, and she said "somebody needs to so something about that too."
Fast forward a month and we all were on a road trip to see a friend graduate from basic in the army. The three of us shared a hotel room with two beds, and after dinner we went back there for the night. We take our showers and such and get into night clothes.
I'm in one bed, and my best friend is in the other bed, watching TV, and my girlfriend comes out of the shower, and walks past us in a towel. She pulls back the covers, gets in with me, covers herself up, then pulls the towel out from underneath the covers and tosses it across the room, as she does I can see she is naked.
We all kinda play it cool, but then she reaches under the covers, puts her hand up the leg of my shorts, grabs my cock and starts stroking me. At first I am looking at her like "what the fuck are you doing?" but I was certainly not gonna stop her.
All of a sudden she says "OK, time to suck it." and pulls the covers over her head, pulls my cock out and puts it in her mouth.
So I am laying there getting my cock sucked by my girlfriend who is completely under the covers, and my best friend is a few feet away. I look over and we meet eyes, and are both just stunned in silence, watching the blanket move up and down. After a minutes or so she says "It's hot under here," and pulls back the covers, revealing her face, and my cock in her hand as she strokes it. She gives it a couple of sucks, looks over at him and says "Do you like the show so far?" He is wide eyed, and nods "yes."
She goes back to sucking, not bothering to hide what she is doing and putting on a show for both of us. The blanket is slipping off, and she is now mostly uncovered as well, and he is seeing her naked for the first time. She is glancing over at him occasionally, and I can't help but notice he is hard. She says "You can get that out if you want. It's like live action porn." and laughs. I could tell he thought about it a second then he says "OK, fuck it," and pulls down his shorts, and lays back revealing his hard cock. She says "nice!" and smiles at him. I think he was pretty red faced, but said thanks, and she said "No really, that is a nice cock, it's actually pretty big." He said "thanks," again kinda shy, and started slowly stroking himself. She went back to sucking me for another 30 seconds or so, but was watching him stroke.
Suddenly she stopped and said "I think it is time for the next act." She got off of me, standing naked between the beds, and kinda pulled me up, and had me sit on the edge of our bed. She faced away from me, straddled my legs, and backed herself down onto my cock, reaching down between her legs and guiding it into her pussy. She slowly took it up and down a few times, before settling down onto me fully. I was leaned back with my hands on the bed behind me.
She rode me slowly a minute or so, and was now watching him stroke his cock a couple feet in from of her. Then she turned to me and said, "can I ask him?" I said "Uh, sure."
She goes back to watching him and says "Can I suck that for you?" He was shocked, kinda blinked and said "I uhh... yes you can." Then he looked at me, and I nodded my approval.
She had him sit on the edge of the other bed in front of her, taking his hand and guiding him there, once he was sitting there, she reached out and took his cock in her hand, stroked him a bit, then told him to sit back, leaned forward and took it into her mouth. I could tell she was doing a great job, and his head rolled back.
She was now taking a cock at both ends for the first time, and my best friend was getting his first blowjob.
After a minutes or so the position was a bit awkward and she told him to stand up in front of her. He did, and she resumed sucking, and started bouncing on me more. He was clearly enjoying it, and I was as well. I watched her reach out, take his hand, and place it on the back of her head, she stopped sucking long enough to say "you can pull my hair if you want," and I saw him slowly wrap his fingers in it. Maybe 30 seconds later he his hand around her hair like it was a ponytail, and was starting to fuck her mouth. Suddenly he said "I'm gonna cum.." she mumbled "MmmHmm" reached her hand up, and started stroking and sucking him off into her mouth. I could see his cock twitching into her mouth, and his head rolled back, and could tell she was swallowing. Seeing that made me start to cum as well, I said "I'm cumming too." and she started grinding on me again, his cock still in her mouth. I came in her pussy, and it was intense.
So yeah, that was how the first time we shared her went down. There were a couple other times.
Some months later we finally had a threesome together. It started out with her and I talking about how he needed a girlfriend, progressed into her letting him touch her, was a cute thing. I remember one time in particular, she came over to hang out at our apartment, he was looking kinda sad. She said "would boobies help?" He said "I think so." She got up and went over and put her sweater over his head for a few minutes. Not only was it cute and fun, but it was pretty hot. She only stopped when she got embarrassed and shy because he put one of her nipples in his mouth.
So, it actually started out fairly innocent and cute. Eventually she took both of our cocks in pretty much every way a girl can take them. She's gone, but he and I are still best friends. No regrets at all. It was a lot of fun for all of us, and no drama.
Another time we were out of town at a fancy hotel for a friends wedding. Sharing a room. had a big shower. Her and I went to shower together, and he said jokingly "I'll be in in a minutes." She said "OK, cool." and smiled. A few minutes later he joined us. She was between us, taking turns washing us, and we had her super soaped up and our hands all over her. A few minutes later we rinsed, and she started taking turns bending over and sucking a bit on each of us. Before long she said "I want to see if you both fit in my mouth." We wrapped our arms around each other like bros, side by side, and she got the head of our two cocks together and sucked them both for a bit. Her looking up at us like that was super hot. She put on a show of it.
We were all having a blast, laughing and joking. She made us both cum. Stroked each cock into her mouth. We double-penetrated her later that night after the wedding.
That girl was a lot of fun to play with. That lasted a few years, we did all kinds of stuff with her. We were all experimenting at that time. He and I have shared three other girls as well. He started dating a girl while I was still with my girlfriend, and we traded them a bit. Mostly blowjobs but we did fuck both of them together a few times.
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My wife's awakening
So my wife was 19 and in college when we first started dating. We met through mutual friends at a house party. Now we have been together almost 13 years. I'm a decent bit older than her, but she was pretty mature..I would probably say more than me at the time. She was pretty inexperienced, and had only been with two guys, both were kinda vanilla. She grew up in a really conservative Christian house, but was pretty ready to throw off all of that, and was certainly ready for new experiences.
She was living with her ex at the time, and that was super awkward, so a few weeks after we got together I asked her to move in with me and my best friend. She accepted. She slept on the couch the first night or two, but pretty quickly I invited her to share the bed with me.
I tried to play it cool, but the very first night she slept in my bed, she came out of the bathroom in just a tie-dye school t-shirt and white cotton panties with her blonde pony tail up, and was just gorgeous. The lights went out, we started kissing, and maybe 10 minutes later her panties were off and she was on top sliding herself down onto my cock.
After that it was on. I was in heaven. Fucking a beautiful, fit 19 year old college girl, teaching her new things. She was pretty willing to do just about anything. I took a few pictures of her at the time, but about a year later I told her I had always wanted to try to do boudoir photography type of stuff, and she said "Sure! I'm down. What do you have in mind?" We started experimenting with it after that, and were shooting pictures a few times a month.
I've used, and taken pictures of her in pretty much every conceivable way with my cock and multiple different toys, tied up, etc. I've seen her take toys in her mouth, pussy, and ass at the same time. We experimented with all kinds of things. Had a lot of fun, getting to know each others thoughts and kinks. In the next year or two she did pretty much anything I asked her to do.
I remember the first time that anything with anal sex came up. We were fucking, and she was on top riding me. I had my hands on her ass, and my finger was sliding closer to it. After a bit I just kinda went for it, and ended up with my middle finger in her ass, pulling her up and down on my cock that way. She went crazy, cumming and moaning, and ended up literally shaking with an orgasm. It was beautiful. Afterwards she said that nobody had ever done that before, and that it was the hardest she had ever gotten off.
A month later after a few more times we tried to get my cock into her ass. That didn't work. I bought her a little thin dildo anal trainer the next week, and we started playing with that. After some time with that, and lots of lube, she took my cock in her ass in place of the toy.
Fast forward about a year. Her toy collection grows, we've been experimenting with her taking a bigger dildo, and we have just checked into a hotel room to shoot pictures and have a fun out of town weekend. We are in the room maybe 20 minutes. I'm fucking around on my phone and getting unpacked, and she is in the bathroom, and yells "Hey, come in here a second!"