This story involves me, my ex girlfriend, and a family friend (all 19 at the time). My family had a summer house on a lake. We lived in a small bay which connected to 7 other properties via a single dirt road. All of the families were pretty friendly with each other and one had a son my age who I'll call Richard. Richard was a really nice guy, but wasn't what you would call an alpha male. He was short (probably around 5'5''), thin, and was pretty shy. Needless to say, Richard hadn't experienced any success in the ladies department yet. He was blessed in other ways though; he was absolutely hung, and it looked even bigger on his small frame.

During my freshman year of college, I met Cassie (not her real name) who became my first serious girlfriend. She was great in many ways, but especially great in bed. As you can imagine, we had sex constantly, 19 year olds are horny! She was incredibly sexy, about 5'6, curvy figure with perfect, perky, D boobs and a big ass. It became pretty apparent early on that she brought a lot more bedroom experience to our relationship. Once, she mentioned how hung her ex was and she noticed that it turned me on (you can read that story in my profile). She was a size queen which made me incredibly jealous and horny at the same time.

That summer, we decided to go up to my family's lake house for a few weeks before going back to school. Richard had been up there most of the summer and was excited to see me and meet my new girlfriend. The first few days were pretty normal; tons of swimming, hiking, boating etc. One afternoon I was taking a canoe ride with Cassie and I asked her what she thought about Richard. She told me he was super nice, a little weird/awkward but kinda left it at that. I agreed with her, and mentioned that I couldn't imagine him hooking up with a girl at school, let alone actually getting laid. Then, it dawned on me, maybe Cassie could help him out! At 19, I would have been WAY too jealous and insecure to let her hook up with a normal guy, but for some reason the thought didn't bother me because I knew that Richard was not a threat. So at that point, I suggested that maybe she could help him out. My mouth went dry, and my heart was palpitating. At first she was turned off to the idea and thought it was silly. But then I told her how hung he was and she was intrigued!

We discussed her doing it over the next couple days, both seriously, and during sex which was hot for both of us. She finally told me she wanted to, and that she was excited to get a good stretch. The next morning I went to play golf with Richard and put it all on the table. I told him that Cassie wanted to help him out by taking his virginity. He instantly turned red, and had a million questions but was beyond excited. His only stipulation was that they were alone because he thought it would be too nerve wracking to perform in front of me for his first time. I was totally cool with that and agreed.

When I got back from golf I told Cassie, and she was really excited/nervous. I told Richard to swing by my house after dinner. When he got there, I had a baseball game on and was having a beer with Cassie. We chilled for a bit, nobody really knowing when or how to start this thing. Finally, I spoke up and suggested that maybe Cassie and Richard would like to go upstairs to my bedroom and get to know each other a bit better. He raced upstairs like he was shot out of a cannon. I obviously tried listening, but couldn't hear much. They came back downstairs about an hour and a half later flustered and sexed up and Richard went home.

Cassie and I stripped and got into bed right away and she started stroking me telling me about what happened and it was extremely hot. She told me that at first, she wanted to put him at ease and let him explore her. She stripped naked, got onto the bed, and spread her legs. She asked him to touch her and explore. He started with her beautiful, large, firm breasts. He squeezed them for a while, then started licking her nipples which she loves. He eventually moved down to her smooth innie vagina and started fingering her. She said that he wasn't very good, but really put him at ease. After a while, she told him to strip naked and lie on the bed. She straddled him, and started making out with him. She touched his dick for the first time and was beyond impressed. She sensed how excited he was by his breathing, and precum so she stopped for a few minutes before putting him in her mouth. That didn't last long. After 30 or so seconds he said he was close so she stopped sucking, and mounted him. After maybe 10-20 seconds of riding, he busted right inside her! He was really embarrassed but reassured him it was normal, and he was ready to go again in less than 10 minutes. The second time, she brought him through various positions. She had him do her missionary, then she got on all fours and let him take her from behind.

His skills weren't the best being his first time, but Cassie really enjoyed herself because of how big his penis was. She told me that she really missed being filled like that and would totally be down to give him some more pointers! They ended up fucking several times that week until Richard had to leave. I watched a couple of their sessions and it was fucking HOT. We had a ton of sex too. Cassie was very sore but very happy by the end of the whole affair.

Cassie and I ended up breaking up a year later for unrelated reasons but Richard is still eternally grateful to both of us.