What follows is the story of how I lost my virginity as a young man.
I had always been somewhat reserved when it came to the girls in high school and, although I went on lots of dates, I had never gone all the way with any of the girls I dated. For sure there was lots of heavy petting but I never pushed the issue. I preferred to play it safe because I didn't want to get any of those girls pregnant.
I started Junior college in the town where my mother lived and stayed at her house while going to school. My parents had been divorced for my whole life and my Dad had gotten custody when I was just a baby. So, for all those years I never lived with my mother for more than a few months at a time. Her and I were really more like close friends than mother and son and I always felt comfortable talking to her about anything, including sex. She was the main person to encourage me to not have intercourse until after I had gotten out of college. She didn't want to see me get tied down too early and it made sense to me. The problem was I always wanted to go further and it took supreme self control to say no to the girls who wanted to take it beyond just making out.
During my first year of college I met some really hot girls and saying no was really becoming difficult. I stayed horny all time. As a result I masturbated daily, sometimes more than daily. I talked to mom about wanting to get more intimate with the girls but she always encouraged me to stay celibate until I finished college.
Mom worked nights at a local bar as a barmaid so she was always home when got out of school. This was nice because she could make dinner for me and we could sit and talk or watch movies together. However, it really cramped my style since, after all day looking at all those hot girls at school, I would be really horny by the time I got home and would have to wait hours for her to head to work at around 7:00 PM before I could get myself off.
One day I just could not wait and I told her I was going to take a nap. I went into my room and shut the door. It was an old house and none of the interior doors had any locks. This was usually no problem as Mom always respected my privacy. I got naked and lay down on my bed with a couple of magazines and before long I had a raging herd-on. I applied some lubricant to my cock and started stroking. I liked to take my time and really enjoy the sensations so it wasn't difficult for it to take me forty five minutes to an hour to finish. While, I'm not gigantic by any means, my eight incher is straight and thick and I love to watch my hand moving up and done its length. It may sound a little weird, but part of the eroticism of masturbation, for me, is seeing me hand stroking the length and rubbing the sensitive head of my cock and watching the sperm shoot all over my chest and stomach.
I was well on the way to cuming and had been at it for about thirty minutes when I heard the phone ring in the other room. I ignored it since Mom would answer it anyway. I was just squirting my load when my door swung open.
"Honey, your Dad is on the phone..." she was saying as she came in. I was caught red handed! She had the phone in her hand. She walked over, handed it to me and walked out without saying another word. I was naturally red faced and a little shaken to be seen in this way by my mother but, I put on my best "calm, cool, and collected" voice. "Hi Dad," I said and the conversation went on from there. While I was talking to him I cleaned myself up, put on some shorts and a t-shirt and went into the living room.
When I was finished with the phone I looked at Mom, who was sitting on the couch watching the tube, and said, "I'm sorry Mom. I won't let that happen again."
"Oh, Babe, don't you worry about it. I know you have needs."
"Yeah, but I'm still really embarrassed about you seeing me doing that."
"It's really OK. I know you do it. You're only human after all. I know you have been frustrated sexually because of not having sex. You have lots of hormones rushing about and all that. It's OK. Next time I'll knock."
"But, still..."
""Stop being embarrassed. Hell I do too. It's perfectly natural."
I was shocked. I had never thought of her like that before. "Okay ...I guess"
"Stop being silly, really. I have to go to work now." She said as she grabbed her purse and headed for the door. "We can talk about it some more when I get off tonight, if you're still awake"
And just like that she was out the door and gone. I was kicking myself a little. I hadn't realized it was so close to her leaving for work. I should have waited for her to leave. On the other hand, I was a little turned on by the thought of her playing with herself. I hadn't ever thought of her like that before, but now that I did, I realized how attractive she was. First of all, she was only seventeen years my senior and at 36 years old she was in fine shape. She had a nice figure and ample breasts and a really cute butt. She was what I would call petite at less than five feet tall and weighed in at maybe 110 pounds soaking wet. Second, she was always being courted by men she met at the bar and being taken out on dates by them. I assume she was having sex with some of them, at least. This thought drove me over the edge and I had a hard –on again! What would it be like to watch her getting it on with some man she went out with?
That night, when she got home, I made it a point to be in bed so we wouldn't have to talk about her seeing me earlier. I could hear her moving about in the kitchen and living room for a few minutes and then I heard the shower go on. I couldn't resist. She had seen me naked with my hard cock in hand and now I wanted to see her naked. I crept out into the dark hallway and tip-toed to the bathroom door. Fortunately, it was already open a crack so she wouldn't hear the sound of the door catch releasing when I turned the knob. I pushed the door open just a smidge more. From my vantage point I could look into the mirror and see almost the whole room. The shower was running and she was getting undressed. Her shirt and bra were already off and she bent down pushing her jeans and panties to the floor. Her ass was pointed at the mirror and I got a good look at her bald pussy framed by her wonderful ass cheeks and thighs. Then she got in the shower. I couldn't see her in the shower, but I stayed put, hoping to catch a glimpse of her as she got out. I was in luck because she didn't shower long enough for the mirror to fog over. She shut the water off, opened the curtain and there she was in al her glory. Her wet, blonde hair caressed her naked shoulders. Her breasts wear an ample D-cup, by my estimation, and she had large nipples, at least as big around as the end of my index finger. Her belly was as flat as a board showing her abdominal muscles. Her pussy was shaved clean and I could see her lips hanging down. I saw all of this in the moment before she got the towel off the rack and started drying off. I was too chicken to stay any longer so I crept back to my room.
I went to sleep with visions of her naked body in my head. I had to see her naked again! She told me earlier that she masturbated too. I thought it would be awesome if I could somehow see her ding that.
The next couple of weeks were more or less uneventful. I manage to spy on her taking a shower a couple of more times, but that was it. I found myself envisioning her naked body riding on top of mine whenever I jerked off. I was ashamed of that since it was such a taboo fantasy but, I was also all the more turned on because of the taboo-ness of the whole thing. I figured that it was alright if it was just a fantasy.
Then it happened. She went to work on a Friday night as usual. I went to my buddy's house that night and had told her that I was planning to stay the night over there. As it turned out my buddy, Gary, got an emergency phone call early in the evening and he and his parents headed out to take care of his ailing Grandmother. So I ended up going home around ten o'clock. As I came down the street I noticed that Mom's car was in the driveway and another car I didn't recognized was parked behind hers. I also noticed that several cars were parked along the curb. Evidently Mom thought I would be gone all night and it was a good opportunity for her to have a party with some friends.
I figured I could go stay at Jason's house but I needed to get some things from my room. I didn't want to barge in on her and her friends so I parked down the street. Cutting through a couple of the neighbor's backyards I went to the back of the house. I planned to go into my room through the window, get my things and leave the way I had come. When I got to my window I noticed that the light in my room was on. The curtain was open about one inch in the middle so I crouched down and peering over the window sill looked in. To my shock there was a woman being fucked by two men on my bed. I had never seen any of them before so I knew this was not Mom's regular crowd of friends. The woman was on her hands and knees getting it rammed to her from behind and at the same time giving the other guy a blow job. I was getting turned on. I pulled out my cock and started stroking it.
Just then the guy she was sucking pulled his cock out of her mouth and shot his load all over her face. The guy fucking her wasn't about to stop! The other left the room. The woman, whom I could just barely hear called out for my mother.
"Hey, Connie, bring me a towel!" She yelled.
I few moments later my mother appeared with a hand towel. She was completely naked! My mother was having a swingers party and letting people fuck on my bed, probably all over the house by the number of cars I saw parked out front! Then she did something I will never forget.
She came around and instead of handing the towel to the woman she bent over and licked some of the come from her face. The woman giggled a little and Mom continued to lick up the cum until the woman's face was clean! Then she started French kissing the woman! I was so turned on by how slutty my Mother was that I shot my load in the flower garden right then and there! The guy fucking the woman pulled his cock out of her pussy and Mom rushed around and took his cock in her mouth. I could tell he was giving her his cum by the ecstatic expression on his face. I knew for sure when she got up and went around to the still kneeling woman and allowed some of the thick white cream to drizzle from her mouth into the other woman's mouth! Holy Shit! My mother was right there in front of me cum swapping with another woman!
I would have stayed longer but I heard the patio door sliding open. Someone was coming out to my backyard! Really fast, I ran around the corner of the house and then made my way back through the darkened yards the way I had come in. I didn't get to see anymore but I had learned some very interesting things about my mother's sexual appetite that night. Things I would later use to my advantage.
I didn't say anything to Mom about having come home that night and several days went by while I thought about the whole scenario and what to do with my new found knowledge about her. In the end, I decided that, somehow, I would really like to have sex with her. So I concocted a plan to seduce her.
Over the next few weeks I started walking around the house in nothing but my underwear, rather than a pair of shorts. I also made it a point to complement her on her looks or how nice she looked in her jeans or how lovely her hair was; things like that. She didn't seem to notice my body at first so I kicked my plan up a notch.
One early evening before she went to work I got her to watch a movie with me. She put in the video and got some popcorn going in the microwave. I went to room and stripped down to my undies. I grabbed the blanket off my bed and got on the couch all wrapped up in the blanket.
