Where it happened: Neighbors house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time ended up being a surprise to me, but in hindsight I believe was pre-meditated by my next-door neighbor.
I was 14 at the time and was quite well developed physically, but I was somewhat naive about sex. It happened during my summer vacation when I had lots of time on my own. I was still at the age when I would play with the neighborhood kids but was beginning to have ‘other’ interests.
My next-door neighbor was around 43 years old and she was married to a much older man (60ish). Since it was hot, my friends and I often asked the neighbors with pools if we could swim. My next-door neighbor was often around and allowed us to do so. She would sit alongside the pool and supervise us as our group of 5-6 boys would have a great time.
One day when our swim was ending and I was the last to leave, she asked me if I had ever skinny-dipped. I said that I hadn’t and she suggested that I come over some time and try it out. I didn’t think anymore about it at the time.
A couple of days later while I was home alone, my parents told me to cut the grass. It was hot and I cut the grass only wearing a pair of shorts and was sweating profusely. My neighbor came out on her pool deck and called over to me that I should come over for a swim to cool off. I thanked her and told her I would be right over.
I met her on her pool deck and quickly jumped in and began swimming as she watched. After a couple of minutes, she told me that she was going inside to fold the laundry and if I wanted to, now would be a good time to try skinny-dipping.
After she left, I took a chance and removed my swim trunks and was shocked at how good the cool water felt streaming across my cock as I swam. I was instantly very hard and excited. I even swam on my back such that my cock stuck up out of the water as I swam. After a few minutes, my neighbor opened the patio door and walked out in a towel.
Somewhat caught off guard, I swam to the other end of the pool to avoid her seeing my erection. Instead of sitting in a pool-chair like she usually did, she walked to the pool ladder, turned around and shed the towel. I was surprised to see her naked backside and she descended the ladder into the pool.
She slumped into the water such that I could not she her nakedness and began to circle the pool. I kept a distance from her, but could not keep my eyes off of her, hoping to catch a glimpse of her body.
After a couple of minutes of avoiding her in the pool and contemplating how I would exit the pool to retrieve my trunks without her seeing my erection, she called me over to her in the shallow end. I slowly made my way over to her, carefully to keep only my head above water.
As I approached her, she asked me to retrieve the floating pool mattress from across the deck. As I hesitated, she stood up in the water revealing her breasts and told me not to be shy, that she’s seen it all before. Since she was so non-chalant about it, I got out of the pool with my back toward her and grabbed the pool mattress. However, once I lifted the mattress with both hands and began to turn back to the pool I realized that my erect cock would be in clear display. I tried to hide my swollen member using the mattress, but it was a lame attempt and I knew that she had seen my swollen member. As I jumped back into the pool, she thanked me and told me not to be ashamed. She said it was natural and that I had a very nice body. I blushed and slipped back below the water.
What happened next astounded me as she climbed on top of the mattress and laid out flat on her stomach atop the mattress. As I watched her climb aboard, I got a nice look at her somewhat sagging breasts and a quick glimpse of her dark bush. She then laid out in the sun, front down with her ass in the air with her legs tight together. I could not see anything but my cock was nearly bursting with excitement.
Over the next few minutes, I swam circles around her hoping for another glimpse of her breasts as she re-positioned herself. Finally, she called to me to ask if I would get her the suntan lotion from the pool deck. Fortunately, I could reach it without leaving the pool and returned to her. She then asked me to rub it on her back.
I approached her as she floated on the air mattress and squirted the white liquid on my hands. It instantly reminded me of cum. I spread on my hands warming it up, then put my hands on her back. I began rubbing it across her shoulders and down the middle of her back. In order to reach across to the other side of her back, I had to stand very close to her. As I spread the lotion across her skin, I marvelled at how soft she felt and my cock was aching and I’m sure that I was leaking pre-cum. As I thought I was finishing the job, she asked me to rub the lotion on her lower back where she could not reach.
I began rubbing the suntan lotion across her belt line and slowly across the top of her ass cheeks. She told me that it felt really good. As I was finishing applying the lotion, I suddenly felt her hand on my erection. I froze in place as the feel of her grip sent a spasm of pleasure through me. I hesitated and as she continued to hold my member, she asked me if I was done. I said yes.
She then smiled and let go of my erection and asked me to do her legs. I waded down to the other end of the air mattress and began applying the lotion to her thighs, careful not to approach the base of her ass cheeks. I worked my way down her thighs, to the back of her knees and then to her calves. As I did so, I was inadvertently pressing my raging hard-on into the side of the air mattress as I went. Finally, I reached the end of the air mattress and I realized that I was staring up at her body from behind. As I massaged the back of her lower legs, my cock would briefly contact her feet. As my excitement grew, I began to reach farther up my legs and my erection was now clearly rubbing against the soles of her feet.
Suddenly, she began to move and I stopped. As she repositioned herself, her legs spread open a bit and I could clearly see her dark furry snatch and the outline of her pink labia poking through her fur.
She jumped of the air mattress into the pool and came face to face with me. I thought she was going to get mad at me but she just stared me in the eyes and asked me, “Have you ever see a woman naked before?” I replied yes, but only in magazines. She then said, “Lets go inside and I’ll let you see my body”. She grabbed me by the hand, not giving me much option but to follow. As we crossed the deck she grabbed some towels and began to dry herself as e made our way into the house. She quickly led us down the hall into her guest bedroom and turned around, dropping the towel.
“Do you like what you see?” she asked. As I stood their naked before her with my erection poking out toward her, I mumbled “yes”. She grabbed my cock in her hand as she looked into my eyes and asked if I wanted to touch her breasts. I replied “yes”.
As I brought my hands to her small, slightly sagging breasts she slowly kneaded my cock with her hand. My hands explored her soft breasts and I flicked my fingers across her nipples. She moaned slightly and then sat down on the bed. I could see her dark bush, but her legs were too tightly closed to get a good look at her pussy. As I continued to play with her breasts while standing before her, she brought her mouth to my cock and slowly took it into her mouth once fully, before releasing it and looking up at me.
She said “I think we’re both really horny but we can’t have sex because its against the law. However, there is nothing stopping us from fooling around a little and getting ourselves off. Do you ever masterbate?
“Yes” I replied.
“Good” she said. “Here’s what we’re going to do. I’m going to lay back on the bed and play with myself and you can jerk-off for me while I watch”.
“OK” I replied.
With that she scooted back on the bed and spread her legs wide and began to circle her pussy lips with her fingers. As she did so, she pubic hair parted and I could see her pink pussy lips clearly.
I began to stroke my cock gently in rhythm with her fingers. I kneeled my knees at the edge of the bed, directly below her spread legs such that I was looking directly at her pussy as I stroked my cock.
She watched me pump my cock as she picked up the pace of her rubbing and soon she started to wimper a little. I could now smell her pussy clearly and I was getting close to coming. Then to my surprise, she told me to feel her wetness and spread it on my cock. I ran my hand across the opening of her vagina and labia and felt my hand get soaked in her pussy juice. I then applied this to my cock and couldn’t believe how slippery it made my stroking. The knowledge that her pussy juice was on my cock, the experience of touching my first pussy and the slipperyness of my lubricated cock resulted in me cumming in 4-5 strokes. As I came I could it in my hand and she smiled at me.
She grabbed my cum filled hand with hers, then spread my cum on her belly and breasts. She asked me if it was good and I replied “Yes”.
She then asked me to lay down on the bed so that she could cum. I laid down on my back and then she climbed on top of me. As her breasts dangled down over my face, she lowered her pussy to my lower stomach and began to rub it across my pubic bone. While my cock way now limp and still leaking pre-cum, I could feel it make contact with her as she rubbed herself forward and back across my groin.
I began to play with her breasts with my hands as she worked her clitoris onto my stomach. As I squeezed her nipples she would flinch and lightly moan and she started to more rapidly thrust her pelvis into mine. I could now feel my cock getting hard again and as she ground her pussy onto me, I could feel it poking at her below her pubic mound. Feeling my hard cock beneath her, she slid back slightly and began running her clitoris and labia along the shaft of my hard cock. She was now sweating considerably and she was getting more frantic in her thrusting.
As she starting into a low, rhythmic moaning I squeezed one of her nipples quite hard and she started a quick burst of rapid pelvic thrust on top of my cock as she tried to reach orgasm. On one of these thrusts, the head of my cock popped up slightly and as she slide back down me the head of my cock caught the opening to her gaping wet pussy and I slid deeply inside of her.
I still have a hard time explaining the feeling the first time my cock slid into her pussy. I felt a gush of warmth around my cock and an unreal sensation of slippery, cushioned penetration around my cock-head. I was instantly close to cumming again.
Before she could react to my accidental penetration, she had already begun her next pelvic thrust and I felt the walls of her vagina slide across the length of my cock again. While she was now on the verge of orgasm and made a valiant attempt to avoid a second penetrating thrust, my body had already reacted instinctively by meeting her backward thrust with a forward push of my own, keeping me inside of her as she squirmed on top of me. Then, as the feeling of her pussy being filled by a cock merged with the sensations on her clit and nipples combined, she started to orgasm on top of me.
She started moaning “Oh.. ..my.. .God.. .I’m…cumming…” as she abandoned her attempt to eject me from her love nest and simply drove herself down onto my cock 5-6 more times.
as I had never had sex before and the feel my cock inside an orgasmic pussy was too much for me, I quickly emptied a copious load of boy cum into her quivering pussy.
She lay on top of me for a moment with her breasts flat on my chest before saying “We should not have done that. It isn’t right you know”. I replied “I know, but it felt pretty right to me at the time”. Then my cock twitched inside her again and I could feel myself getting hard again.
We lay there for a moment before she allowed me to climb on top of her and fuck her one more time with me on top.
Throughout the rest of that summer, I was invited over for many ‘swims’ while my parents were away. Needless to say, I didn’t do many laps but I got her very wet quite often. Unfortunately, her husband retired and they moved away the next year but I will never forget her.
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