Jenny’s Gift

Anal

This is a story about a woman that I will always remember with gratitude and lust even when I am too old to do anything about it. Jenny was a young girl, my own age that lived several houses down the block. Jenny was what I would now call an “athletic” girl, not really a “tom-boy”. She played baseball and soccer on my little league teams since I was six years old, and certainly was as good as most of the boys on the team. She was also very pretty, but was feminine enough that you knew that she was more than “one of the guys”.

Jenny was also my friend, but not so close that we spent too much time together. Because of the convenience of location, she would sometimes practice soccer or throw the baseball with me. She was also a good swimmer at the local community pool where we were both members.

Jenny and I went to the same school, and sometimes we would walk home together. I really enjoyed her company, but at that age we still couldn’t be too close without being subjected to a tough time from our peers. Well, time has a tendency to progress, and we both started to mature. I really noticed some major changes had developed when we went to the swimming pool for swim team practice. Jenny had developed tits, and such a delicious looking figure that I couldn’t help but gawk.

The summer before our senior year in high school, things really began to change. The hormones were definitely flowing in both of us, and I was also sporting a bigger bulge in my swimsuit. She had the same natural beauty that she had when she was little, but now had the sex appeal of a young but maturing woman.

Jenny would have her eighteenth birthday in a few days, and we had gone from “kids” to the “seniors” of the school. Our birthdays were only days apart and it was not unusual for us to celebrate our birthdays together. I guess we had done something together on our birthdays for so many years that in fact it had almost become a ritual. Now, number eighteen was only days in the future.

Jenny and I had been friends for over twelve years and really knew each other better than average, but now the circumstances were changing dramatically. I really thought that Jenny considered me the “nice nerd kid” that lived down the block. To be honest, I always had a crush on Jenny, but thought that she was probably too good to ever be interested in me. In the past year though, the reality was that I also had changed. I had grown to be almost six feet and actually had to shave – at least every few days.

As our birthdays approached, I happened to see her after swim practice. I was having trouble keeping my eyes off of her magnificent figure when I finally realized that she was talking to me. I had to concentrate to avoid staring at her chest while she began to explain to me that she was hosting a small “girls only” party this year to celebrate her birthday. She did mention that she hated to break our tradition of celebrating together however, and hoped that maybe we could do something together around my birthday to keep up the tradition. To be honest, I was thrilled that she would remember, but didn’t really expect anything to happen.

My eighteenth birthday happened to be two days before school started for our senior year. I was really just planning to have pizza with my family and a few boring friends from the swim team. Maybe we would even go out for a movie afterwards. The evening before my birthday however, the doorbell rang and I was surprised to find Jenny outside carrying several presents. She said that if I was not busy, she would like to go for a walk with me and give me a present. She also brought a small cake that she had baked herself.

I could hardly take my eyes off of Jenny. Her beautiful dark blond hair hung down on a tight white tank top, framing some exquisite rounded breasts. I opened the rectangular gift that she presented to me and found a framed photograph showing the two of us together as young children playing in the mud. The image caught the innocence and joy of youth. It was definitely a unique gift that could not be equaled. After I put the presents inside the house, we walked together a couple of blocks to the park where we had spent so many hours together over the years.

Twilight had come, and we talked about our many fun memories from the distant past. The first slight chill of autumn had filled the air, and while I tried not to stare, Jenny’s nipples were tenting the fabric of her shirt forward. I don’t quite know quite what came over me next. Somehow, I had the nerve to lean forward and give Jenny a kiss. I almost felt dizzy when her lips met mine, and her soft breasts nestled against my chest.

“That was really nice,” she said.

I can’t believe it, but I admitted that it was the first time that I had really kissed a girl. Jenny simply smiled at me and told me that she was pleased that she could be the one. A minute later, Jenny kissed me again, but during our kiss she took my right hand and guided it under her shirt to her left breast. She was not wearing a bra, and it was my first opportunity çekmeköy escort to feel the unique softness of a woman’s breast and her erect nipple. I almost felt weak at the knees. My face must have flushed and we both knew there was an obvious pressure in the front of my pants. I was really embarrassed, I am also sure that Jenny felt the pressure exerted between us.

“Happy Birthday,” Jenny said as she smiled and gradually began to lead me back toward my house. I know my heart was pounding as I felt a sensation like none I had ever felt before deep in my soul. I don’t think I will ever quite forget that birthday present.

Soon school started and life quickly returned to the usual routine. Jenny and I were both very busy once the activities of school began. While I certainly would have liked to have spent more time with Jenny, I realized that it just wasn’t practical, nor did I seem the type to fit in with her usual friends.

The next two months flew by. I would occasionally see Jenny in the halls after classes. She was always very friendly and occasionally would give me a hug. As I mentioned before, she was exceptionally beautiful, not to mention very popular at the school. Jenny was elected a varsity cheerleader, but despite her numerous commitments, she maintained a very good academic average. While I did well (particularly in swimming), I was far from being someone that most people would consider exceedingly popular. To be honest, I did not think that I was in a league to be taking her out. I pretty much just hung out with some boring guys from the swimming team, and occasionally would go with friends to the movies.

One day in the locker room, I overheard one of the football “studs” talking about how he had taken Jenny out on a few dates, but that she would never do anything. His friend quickly agreed, telling him that he heard that she never let anyone go beyond a kiss before she would say she had to go. I could only smile remembering our time a few months earlier.

A couple days later, I saw Jenny in the hallway, and she asked me if I would walk home from school with her. We made some light conversation, and soon we were standing in front of her house. She gently asked me if I was going out with anyone special. I told her no, thinking that this was just polite conversation. Suddenly I heard her asking me if I would take her to the prom. I’m sure that I must have looked like I had just seen a ghost.

The senior prom was not for about two months, but it was the biggest social event of the school year. I was caught totally off guard, and heard myself saying, ”Are you sure that you really want me to take you?”

She looked me straight in the eye, and said “Are you going to ask me, or do you want to look for someone else.”

“Of course I want to take you,” I mumbled. “I just didn’t think you would want me to be your date.”

“Not only do I consider that to be a commitment to the prom, Ben, but I am really hoping that we could do a few more things together, ” she said. With that going through my mind, I practically floated home.

We began by getting together to study in the evenings, and soon were occasionally picking up pizza toghether after the ball games. One night, she asked if I would bring her home following a school basketball game. She made a point of telling some of the other cheerleaders that her boyfriend was taking her home. When we went back to her house, she invited me in to watch some television. I noticed that the rest of her family had gone out, leaving us alone. Jenny was still wearing her cheerleader outfit, and she really looked stunning.

After a few minutes, she mentioned that her back was stiff and asked me to give her a back rub. The top of her outfit made rubbing her back quite difficult, and she quickly pulled it over her head. She still wore a sports bra, and I began by rubbing her shoulders and relaxing her muscles. In a couple minutes, she pulled the bra off telling me that it would make things easier if I didn’t have to work around the straps. I felt her soft skin and tight muscles as I gently massaged her back. She would occasionally moan her approval, and eventually told me that it felt much better. She turned to face me, and I almost choked as my eyes were riveted to her beautiful breasts.

Jenny smiled and told me that somehow she just knew that I would like looking at them. Jenny’s chest was about a 34 C, with perfectly shaped breasts and silver dollar sized aureoles. Just then, we heard her parent’s car pulling into the driveway, so she kissed me and slipped her top back on. As I was leaving, she said that she had something special planned for Saturday night, and asked me to pick her up at 7:30 for a surprise date. She said that she wanted to give me some special inspiration before the following weekend when I would be swimming at the State Championships.

That Saturday, when I arrived to get her, she told me that we would need to go to her Aunt’s house to take cevizli escort care of some pets that she was responsible for tending while her Aunt was on vacation. It only took a few minutes to drive to her Aunt’s home, and we soon entered a beautifully decorated house. Jenny fed the cat and brought in the mail. She then turned to me and told me that the surprise date was to spend some time together at the house, including the hot tub. I knew that we hadn’t brought any swimsuits along, so it didn’t take me long to figure out that we would soon be skinny-dipping.

While the water was heating, she reminded me not to tell any of my friends about our upcoming adventure. Then she suggested that I continue with the back rub that I had been giving her a few days before. With that, she slipped off her shirt and lay face down on a couch. I went over and began to rub her back, feeling the soft pliant skin. As I ran my hands across her back, I ran into the obstruction of her bra strap, and she mentioned that I could unsnap it, as I needed to get some practice removing it. I popped the clasp, and was now able to run my hands down to the waistband of her shorts. After a few minutes, she mentioned that she also wanted me to do her legs, and with that raised her hips so that I could slip her pants off. Now the only thing covering her was a tiny pair of blue satin bikini underwear. I continued to massage along her back extending down her long beautiful legs. The sensation of touching her skin and feeling the reaction of her muscles was very exciting. Eventually, she thanked me and said that she thought that the water was probably ready. She rolled over, and again I was greeted with a view of her gorgeous breasts.

“Okay, lets head out to the hot tub, and then it’s my turn to undress you.” She led me to the patio, and slowly unbuttoned my shirt and eventually slipped it off. After a couple kisses, she unzipped my pants and lowered them. I was already stiff, and sporting a tent in my underwear. “My, it looks like you are glad to see me,” she commented. “Well, I’ll take care of that later, but get in the hot tub for now, and I will join you in a minute.”

I felt rather nervous as I slipped off my underwear and climbed into the tub. The warm water was soothing, and I sat back soaking and looking up at the stars. The light was low and only some reflected light from the house illuminated the porch area.

In a couple minutes, Jenny came out with a couple towels and cold drinks. then quickly jumped into the water. She was wrapped in a huge white towel and had put her hair up so it wouldn’t get wet. She looked truly spectacular. When she unwrapped to get in, there was still obviously nothing on her top, but it looked like she had put on a skimpy thong bikini bottom that barely covered her pussy. Initially she sat on the opposite side of the tub making small talk, but soon we were laughing and enjoying ourselves just like when we were young kids. Jenny had a wonderful way of making me feel so relaxed and confident.

After a few minutes, she moved around to sit by my side. I could feel the soft skin of her thigh against my leg, and she leaned over and put her head on my shoulder. Soon we were kissing, and I felt her soft breast against me. Despite the warmth of the water, her nipple was erect and poking out. She gave a soft moan as I lightly rubbed her breast.

“ Do you think you would like doing that more often?” she said with a laugh. Next I felt her hand gently grasp the shaft of my penis. It was already as hard as it had ever been. “I think that this has grown since I last saw it,” she commented.

At first I felt slightly embarrassed, but soon I was just enjoying the magic of the moment. I reached over and kissed her while gently stroking her supple breasts and feeling the erect nipples. My hand slid down her abdomen until it reached the top of the thong. I could feel a wisp of soft pubic hair over the edge of the material. I was ready to slide my fingers under the edge when she stopped me.

“Not yet,” she said softly. “You will get your chance in a couple weeks, but if we go there now, I don’t think that I will be able to stop, and it’s not safe yet.” She paused briefly. “Tonight is your night to enjoy, and my job will be to give you some confidence in yourself. Hopefully you can take that with you to the meet, and you can really show everyone what you have within yourself. I know Ben, and I believe in you.”

Suddenly she jumped out of the spa and said, “ I need to run to the bathroom. When you are ready, grab a towel and come inside, but don’t get dressed yet.” She scampered off into the house, her tight butt and boobs bouncing as she moved.

In a few minutes, I got out of the water, wrapped a towel around me and walked into the house. She greeted me, now wearing only the navy blue satin bikini underwear again. She grabbed me, rubbing her breasts against my chest and repeatedly kissed me. My erection had never really gone down, but within seconds erenköy escort it was at full staff again.

She sat me down on a sofa, and whispered in my ear. “Maybe this will give you some confidence about how much I believe in you, and care about you. Think about this when you go to the meet next weekend.” She gently began kissing her way down my chest and abdomen. Pausing, she looked up at me, her gray-blue eyes meeting mine. My erection slipped between her soft breasts, and she squeezed them around it. A small drop of fluid appeared at the tip as she gently grasped me.

“Ben, I hope that this will feel good, but bear with me because I have never done this before.” She took my hard penis in her hand and guided it into her mouth. The sensation was unbelievable, but only intensified by knowing that she was really showing me how much she cared about me.

She gradually began to speed up her movements, and I knew that it would not be long before I would be shooting my load. She briefly paused and said, “ I don’t know if I can swallow, but I will try or you can shoot it on my tits.” Within seconds, I erupted with the first shot into her mouth, and the next few jets of semen spraying onto her beautiful breasts. She massaged the cream over her nipples. I was just eighteen with no prior experience, but that event, combined with the intensity of my emotions for Jenny, provided one of the most intense orgasms I have ever had.

We stood and kissed, and I could taste a bit of my own semen on her lips. I reached down wanting to stroke her pussy and provide her the same relief that she had given me. My hand slipped down over the soft mound of her pussy covered by the satin underwear. I could feel the satin material was saturated by her vaginal secretions, and beneath this there was a slight depression formed by her vulva and slightly firmer labia. She quivered when I ran a finger along the slit obviously rubbing over her clitoris. She briefly rubbed against my fingers, but then withdrew. I could smell her special “perfume” on my fingers.

“That will have to wait for a couple weeks until things are a bit safer.” She paused and said, “Don’t worry, it’s yours, but you just can’t have it quite yet.” She then smiled at me with a whisper. “ I did start taking the pill last week, so I think you may get a special surprise after the prom.” She then said that we needed to get dressed and go home before there were any problems.

When I mentioned that I wished that I had been able to give her the same wonderful satisfaction that she had provided, she looked at me and said, “Don’t worry, I’ll take care of myself tonight after I’m home, and I will be thinking about you the entire time.” Then before getting dressed, she slipped the satin panties down just long enough to give me a view of the most beautiful sight this side of heaven. Her light brown pubic triangle was trimmed, but full enough to look like a real woman. “Just think about that when you are getting ready for your race,” she said. I took her home, kissing her deeply before watching her go into her house.

A few days later, Jenny brought me a present when I was getting ready to leave for the state championship swimming meet. It was being held at a university pool about 200 miles away, and I would be staying in some dorm rooms with a few other members of the team that had qualified. I certainly wasn’t expected to win anything, but I felt very proud to represent my school. There was always hope, and my coach had repeatedly told us, “In sports, just about anything can happen.”

Jenny gave me a small rectangular package and told me to open it when I got there, but said that I may not want to open it in front of my parents. With that, she gave me a kiss, told me that she believed in me, and turned and ran off. I knew that my parents would be driving down to watch me swim, but at that point, all I wanted to do was not disappoint Jenny.

When I arrived at the meet with the rest of my team, I found that we were unusually lucky, and had been assigned individual dorm rooms for the two nights of the meet. When I got settled in my room, I unwrapped the package that Jenny had given me finding a wooden box about the size of a cigar box. When I opened the box, I found a note from Jenny and her blue satin panties.

The note was short and simple. “I believe in you Ben, and know that you are the best. Think of me before the race, and I will be with you. Love, Jenny.”

The crotch of the underwear had the delightful fragrance of Jenny’s secretions on it, and within seconds I had developed a stiff erection. I couldn’t help but begin to masturbate while thinking of Jenny and how beautiful she had been at her Aunt’s house. I soon ejaculated a thick load of semen while I imagined holding Jenny’s tight body with her soft breasts against me. There was no doubt I was motivated to do my very best for her.

In the preliminaries, I think I surprised my coach and the other guys on the team when I made times that were much better than anything I had ever done, and I qualified for the finals in the 100 fly. My coach even put me on the A-team medley relay instead of another swimmer. Moving me to the “A” squad was quite an honor, because some people believed that group might even place in the finals. That night, I went to the finals of the 100 fly feeling very nervous, but determined to give it my very best effort.

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