My [F]irst Time With An Older [M]an

After I posted my last confession I received a few messages asking me why I thought the age gap was so sexy. I revealed to one of you that I was in an on/off “relationship” with a man who was 45 years old when I was 17 years old that lasted until I was 20 years old. More often than not when I tell friends and boyfriends about this relationship I get a negative reaction from them that causes me to feel upset. I don’t like to tell people. With that said, I was “convinced” to post at least one story and this being my confession account and all . . .

A bit of background: I grew up in a not so nice some-what rural neighborhood with not so nice houses and not so nice people. When I was in the 5th grade “Jeff” and his daughter “Jen” moved into the neighborhood. I later learned that Jeff moved into the neighborhood because his ex-wife got the house. I became close friends with Jen over the next three years. I’d often stay over their house for reasons that I won’t get into. When I was in 8th grade Jeff’s business was financially stable and he bought a nicer house in a nicer neighborhood about 45 minutes away. I was still close to Jen so I’d often spend the weekends at her house with her. Jeff spoke to me as an adult. He was always in a good mood. He never revealed much about himself. He was generous and kind. Even when Jen and I had a falling out during the better portion of the 10th grade, Jeff would call my house to make sure I was doing well. Jeff was a good-looking man. He talked to me like an adult. He became my crush.

I didn’t act on it until right before graduation. It was a weekend in May and I was staying at his house per usual. I hadn’t seen Jeff that day. He had been out. Even though Jeff wasn’t home we (Jen and I) still had a curfew of 11:00 p.m. Jen would normally leave the house around 10:30 p.m. to meet up with her boyfriend and she would sneak back into the house after midnight. I’d cover for her. Sometime past 11:00 p.m. I heard a crash in the kitchen. I go downstairs, walk into the kitchen, turn on the light and I see Jeff standing in his boxers. There was glass on the floor. It took me awhile to look at his face. Once I did I realized something wasn’t right. He told me to go back to sleep, that he’ll clean it up. He was drunk. I never saw him drunk before. I didn’t even know he drank. He stepped on a piece of glass and yelped. He was a mess. I started to clean up the floor. He poured another drink. Once the glass was clean I walked with him to the couch. He sat down. I told him to let me see his foot. I cleaned it. I sat on the edge of the couch. I didn’t know what to do. I never saw him like this. He was always so cheery. He swung his legs upon the couch and said he didn’t want to talk about it.

As Jeff lay on the couch his legs were extended over mine. We just sat in silence and he kept drinking. I kept staring at his body. It looked to me – at that age – like a real man’s body. He then started to talk about what was bothering him. I felt bad for him. As he spoke I began to rub his feet as a comforting gesture. As he talked and without much thought on my part I continued to rub up his legs. As my hands innocently crept up his thighs I noticed that he began moving his hips. I realized that he had stopped talking. I looked at his face. His eyes were closed but his mouth was open. I thought he might have fallen asleep. Yet, his hips were still moving. As my eyes ran down his chest past his abdomen I noticed that his penis was fully erect and pushing his boxers into a tent. I was scared and excited at the same time. I kept massaging his thighs until my hands were brushing against his cloth covered dick. I could hear him moan. I’ll never forget how hard my heart was beating when I reached for his boxers and pulled them down. I slowly touched his dick. I felt the precum and spread it up and down the shaft. I started to give him a handjob, which was a big deal for me. I hadn’t had sex yet and my blowjob experience was severely limited with only one guy who had no staying power. As I was jerking him off I listened to him moan and watched his hips push up into the air. At one point he reached up to touch me but I caught his hand and laid it down. This was enough excitement. I remember that I thought his penis was so big, even though in all reality it was average size. I couldn’t stop staring at it as I played with it. Jeff came shortly after I began to rub his balls with my other hand. It caught me by surprise. I loved it. I remember playing with his cum until he fell asleep. I got up, washed my hands, cleaned him up, pulled up his boxers, and left him on the couch. I didn’t see him the next day.

He was one lucky bastard. Clearly more happened between us after that. But this was our first sexual encounter. I’ll post more if you want more.

[And no, Jen never found out. And no, I don’t feel bad. We went to different schools in different areas and we grew apart.]

Source: reddit.com/r/gonewildstories/comments/485tj3/my_first_time_with_an_older_man