A teenager gets the chance to lose his virginity to the woman of his dreams
This is my first story. Please leave comments to let me know how I can improve.
Thanks and enjoy!
It was the beginning of summer. I only had a few days to really enjoy myself before I had to start working. Work wasn't bad though; in fact it was pretty fun. I was a day camp counselor at my school, and I had 6 weeks of it to make some money. I worked with a few of my best friends and in general the things we did were a lot of fun. Playing games, sports, and all kinds of competitions were a whole lot of fun. This had been my only job, seeing as I was only 16, but if all jobs were this fun I think I would enjoy life.
But as all of us knew, even the adults that ran camp, the best part of camp was at the end of the day at pick up time. With pick up being at 3:30 in the afternoon, most parents that were picking up were the stay at home moms. Needless to say, the kids at camp were as young as 6 years old so the moms were still "fresh." When sitting outside waiting for the kids to get picked up, we would even wear sunglasses to disguise our hormone-filled, perverted stares, but we couldn't hide our jaws on the ground. Now that I think about it, there is no way they didn't notice us.
One day, out of a black Ford Explorer walked the most beautiful mom I have ever seen. Perfect blonde hair that looked like that of a celebrity. She appeared to have just come from working out so she was wearing some tight, body hugging pants that drove everyone crazy. She had the most perfect legs I had ever seen and resting atop of them was a tight and firm ass that made my mouth water just at the site. For a mom, she had the best body I had ever seen, and not to be missed is her absolutely gorgeous face. From head to toe she could pass as a college student but the fact that she was in her thirties made her so much more attractive.
At the end of the camp session we had a swim meet followed by a track meet. The swim meet didn't prove a lot, but the track meet showed me the sexiest mom I had ever seen in my life. She came in wearing a tight black dress which just barely covered her perfect ass. Looking at this woman now gave me the biggest bulge I have ever had. There is just something about milfs that appeal so much more to young guys, and that showed by the enormous and hard erection practically popping through my shorts. I fantasized that she would walk into the counselors' locker room when I am changing. I think about her seeing my rock hard dick and just pouncing on it while her son swims in the pool not too far away. But I knew this wouldn't mean anything as camp was coming to a close and I would never see this goddess again. Until one day a few weeks later when everything changed.
With school approaching I was out and about and as I came home one day I saw the sweetest thing I ever have. I pulled up my hill and saw the kid, Michael, who had the beautiful mom, standing in the driveway of the house right below mine. In the driveway was the black Ford Explorer which carried the beauty. I knew someone was moving into that house and now I knew who it was. I continued to my house and went straight to my room to turn on the tv, but only one thing occupied my thoughts, and it was the blonde beauty who at one point seemed so unattainable was now living just a matter of yards from me. Every possible thought involving her suddenly entered my mind. I thought about the two of us spending day after day doing nothing but fucking. These dirty thoughts instantly made my dick so hard. I had to relieve everything as I pulled my now stone-like member through the fly in my shorts. It was only a matter of time of rubbing my cock before I felt the cum ready to explode. I have jerked off plenty of times, but this time it was different. It was a sensation that I had never felt before and suddenly spurt after spurt of cum was gushing out of me. Each one making my whole body tingle, this was the best orgasm I've ever felt and I knew it was because the blonde beauty was on my mind and was now closer than she had ever been before.
Days went by, even weeks, and the same thing happened, I would see her every now and then and then rush to my room to jerk off thinking about her. One day I was sitting at home alone when I heard the doorbell ring. My parents always told me not to go to the door unless it was someone in our family. I slowly creeped up to the door and looked out the peephole and I just about died. I was looking at the blonde beauty and her son standing on my porch. I forgot everything my parents told me (not that it would have changed my mind) and I opened the door. When Michael saw me he immediately smiled and said, "Chris!"
I bent down and gave him a high five followed by, "Hey Michael how is it going?" By now I could tell that his mom was baffled so I stood up and stuck my hand out to shake hers and I said, "My name is Chris Carmichael, I worked at camp with your son."
"Oh! That's great!" she eagerly replied. "We just moved in down in the house below yours and we just wanted to meet our neighbors. I'm Kim by the way."
Finally I knew her name. I was still in awe just to be able to talk to the blonde beauty that had been occupying my naughtiest fantasies. I was able to keep my composure and politely said, "It's very nice to meet you and I think you will enjoy the neighborhood." She gave me the sweetest smile I had ever seen and it made my heart sink and I was lucky I didn't pounce on her right there. She started to leave after a few parting words but she quickly turned around and asked, "I understand if you can't, but I think Michael would love to have you babysit him sometime. Would you mind? After all, it's hard being a single mom."
"I would love to." That's all I had to say for her to flash that smile again, and I hardly noticed her when she asked for my number to call me. She finally left and told me to be waiting for a phone call because she is anxious to get in touch with me. That's all it took to get the already enormous erection to swell up as much as possible. Once she left, I rushed to my room and began stroking as fast as I could. After a few strokes with Kim on the mind, cum was flying from the tip of my cock to the wall in front of my bed.
The day finally came when I looked at my phone to see Kim calling me. She had an important meeting in a town about 2 hours away and needed to spend the night in a hotel. Before she could even ask me, I said, "Of course I can babysit just tell me what I need to do." We chatted for a little bit and I planned on coming down in an hour to learn how things work. I made sure to look my best because I felt like I was trying to impress her. I showed up at the door and she brought me inside. Kim told me everything I needed to know and what time she would be back the next day. She turned to Michael and told him, "Honey, be on your best behavior for Chris, ok? He is doing me a big favor."
"It's really no problem," I said. She smiled and gave her son a hug and stood up and gave me a hug and a kiss on the cheek. I knew she had to have noticed my face turning beet red. I was short, but she was still a few inches shorter than me. Even in her small frame she had the curves of a model and feeling those against me gave me yet another rock-hard erection. She left and I was sure to be especially nice to Michael and try to be really fun so he would tell his mom how much fun he had with me. Maybe it would lead to future jobs. Later that night, after playing games, it was time for Michael to go to sleep so I made sure he was in bed before I started snooping around.
The first stop was the bedroom of course. I felt pretty sure that it was always the top drawer where women put there underwear so I decided to look there. I slowly opened up the drawer to find a drawer stuffed with lingerie. I picked up a bra and looked at the tag. I had never noticed before, but apparently Kim was hiding some 36 C tits. After rummaging through her underwear for a while I came across something she never expected. It was a huge black dildo. It was very complex with all of the vibrating attachments and such, I hardly knew what I was looking at, but one thing that I did notice was that it was still wet. That really got me going as I felt a familiar rush of blood going below my belt. I found a picture of her and I pulled out my cock to rub one out in the bed that this beautiful woman, who I felt a stronger attraction to than anyone, sleeps each night. With that picture combined with the thought of Kim squirting all over her dildo, I soon found myself feeling the urge to erupt. I grabbed her pillow and I watched loads of my juice flow onto her pillow and I thought of her going to sleep each night be putting her face where my warm cum has been. I went to the guest room where I soon fell asleep with Kim in my dreams.
I woke up the next morning to Michael jumping on my bed asking to go swim. Kim wanted me out by their pool while he was swimming just in case. I got up and ate a quick snack before joining him in the pool. After about 2 hours of playing games and jumping in, we both got tired and thought it would be time for lunch. As we walked inside we heard the front door and in walked the beautiful as always, Kim. She came in and gave Michael a big hug and then she looked at me, still with my shirt off and wet from the pool. I knew I had a pretty awesome body, that was just the fact of the matter. I loved working out and honestly, it showed because I had big pecs and washboard abs. I could tell that Kim noticed immediately as she told Michael to go get changed and walked up to me. With a very cunning smile she said to me:
"I knew you were really cute for a 16 year old, but oh my I had no idea." She reached her hand out to touch my stomach. "I just wanted to make sure they were real." We both chuckled, but as mine was a bit of an awkward laugh, hers was straight to the point. She stepped closer and whispered, "kiss me." I had no idea what to do or say. First I had to make sure I wasn't dreaming but as I felt my face getting red I knew this was real.
"I'm sorry?" is all I was able to say.
"You heard me." she replied in a slightly aggravated tone. "I know you want to. You think you were really being that subtle?" Her tone was becoming much more seductive: "Your eyes moving up and down my body, the bulge in your pants that enlarges when you see me? Please Chris you aren't fooling me so just do what I ask now, what do you say?" That's all I needed to hear so I just leaned in until felt her amazingly smooth, pouty lips against mine. Simply said, it was amazing. I pulled back and told her I needed to get home but I had a lot of fun and would be happy to come by and babysit again if she needed it. "Of course," Kim replied as she saw me to the door and I walked home.
Late afternoon a couple of days later I heard my phone ringing and saw Kim on the ID. I eagerly answered to hear her sexy voice.
"Hey Chris I was wondering if you could come down in a bit and sit for Michael tonight."
"Sure, I will be down in about 30 minutes." That's all I said as she told me she couldn't wait. I got ready, looking my best, and I walked down to their house. She greeted me at the door with a warm hug before I was able to ring the doorbell. She was wearing a low cut top which revealed the C cups which I had never noticed. Below she was wearing some tight blue pants which emphasized each and every curve of her body. Her ass looked simply amazing. She really pressed her petite, yet curvaceous body against me as if she were trying to feel something.
"As I expected." She looked down and to my amazement I was already erect and it was incredibly obvious.
"Oh I'm sorry..." I couldn't collect my thoughts but I finally managed: "It's just that for a mom you are stunning. Thats all, and your body is amazing and I just can't help it."
"Honey I'm not upset. I'm actually flattered that a handsome young man like yourself finds me attractive enough to get like that just by looking at me."
I looked around awkwardly trying to avoid further discomfort. "Where is Michael?" I asked.
"He isn't here. He is staying with his grandparents tonight." She said this with the same cunning smile I had seen on her face many times before. "But I wanted you to come here so I could pay your for your time." I was agreeable to this as I hadn't made any money since camp ended. "But... you know, being a single mother it's hard to make money, so unfortunately I can't give you any money tonight."
"Oh well I could come back another time when you can." There was obviously something I didn't pick up on because she just started laughing.
"I will pay you back in a special way." She put her hands behind my head and pulled me in and kissed me. I pulled back and admired the sexiest woman I had ever seen, and since she had already noticed, I decided to scan her body from up close and see what I had in front of me. Perfection is the only way I can explain what I saw. "It is all yours tonight," her smooth and sexy voice uttered as she pulled me back in for a longer and more passionate kiss.
I had only kissed a girl before. Nothing more. I really didn't know exactly what to do so I just tried to massage her lips with mine and feel how smooth they were. She decided to take the initiative as her lips parted and I felt her tongue squeeze through to my lips. I kissed her tongue at first, which I'm sure was strange, but once I got a hold of myself I let my tongue come out too and before I knew it I was in the middle of the most passionate make out session.
The next thing I noticed was her hand under my shirt as if she was making sure my abs were still there. She moved it down until she began caressing my now solid dick with her hand. Without breaking from our kiss, she managed "Oh my." She finally drew back but only to take my shirt off and she instantly like what she saw. "You are too damn sexy to be 16." She kept her hand wandering up and down my torso, occasionally making a pit stop at my crotch to rub my dick. I didn't want to be too anxious so I just kept kissing her with my hands resting on her hips. She parted from our kiss to say, "Look Chris, don't be nervous, this is just between us, do to me whatever you wish and I will return the favor. You are being shy and I don't want you to hold back one bit." She concluded by grabbing my hands and putting them on each of her ass cheeks and squeezing my hands for me. I didn't need her to do that as I quickly learned to feel it myself. I began massaging it and rubbing deep. It was so firm and it felt amazing in my hands. "There you go. Now keep going." She didn't need to tell me again as I grabbed her shirt-tail and pulled it over her head leaving nothing but a black bra. I stared at her beautiful breasts in awe. I had never been this close to someone's breasts and I wasn't sure what to do first. She assured me that I could do whatever I pleased so I reached back and began fooling with the clasp on the back.
I began fumbling around with the hooks which warranted a giggle from her and she told me to let her do it. A moment later, her bra was falling down and her hardened pink nipples began to emerge before me. Not wanting to be shy and have Kim tell me again, I instantly grabbed them in both hands and began rubbing and squeezing. It was the best thing I had ever felt and I began licking her right nipple and then I closed my lips around it and began sucking on it. With my mouth locked on her breasts I used my free hands to work her pants off which was harder than I anticipated. I finally got them loose enough for her to kick off herself so I could keep licking and sucking on her magnificent tits. A small black thong was the only thing separating me from the first vagina I had ever seen. I sat her down on the edge of the bed which we had slowly stumbled towards as we were locked in a kiss. With her on the bed I knelt down and slowly began inching off her thong leaving me with the best sight ever. Before me was the most perfect pussy in the world. Completely shaven, it looked amazingly clean which made it appear all the more appetizing. She had small but puffy lips and at the top, her little clit was poking out. Overall it was pretty small and looked incredibly tight. I have seen plenty of pussies in porn, but even they didn't look this nice.
I stood up and kissed her some more as she rocked back with her back on the bed. My right hand walked up her leg and began slowly rubbing the aforementioned pussy. From what I had learned before, I figured I should rub her clit so that's what I did. With my first two fingers I rubbed it getting faster and faster while her whispers turned into moans and began getting louder and louder. I slipped one finger down to the hole and while it was very tight, I managed to squeeze it in there and her pussy engulfed my finger. I began pulling it out a bit then sticking back in there as if I were fucking her with my finger.
"Put two in there," she gasped in between her moans of pleasure. I left her clit alone for a minute as I pushed my second finger inside her vagina. I sped it up a little bit and those moans were louder than ever as I felt her getting close I decided to toy with her a little bit and I pulled my fingers out. She looked amazed because I kept her from climaxing.
I kissed her and said "let me take care of everything." She apparently approved because she kissed me back and then lied back down and relaxed. I started kissing down her neck and chest to her perky tits which I sucked on a bit more. I went down her flat stomach and down even further until my lips felt the little button at the top of her lips. I didn't stop there though and I went down in between her lips where my fingers just were. I could taste her juices as she was very wet from my fingers. I tasted it and began licking the outer walls. I slowly put my tongue further inside her and I got deeper and deeper. I started swirling my tongue around her pussy and pushed it in and out. After doing this for a while I moved up to her clit and started by just kissing it. I wrapped my lips around it and I rubbed it with my tongue. Her approval was signified by her now louder than ever moans which by this time were screams. I took my still wet finger and put it in her mouth so she could taste the sweetness that I did. She began sucking on it and I brought it back down to where my mouth was. I squeezed it past her tight lips once more and began moving it very fast. My tongue was keeping up with my finger as I was flicking her clit with my tongue as fast as I could. I kept doing this as her screams told me she was very close. There was no toying with her now and I kept going until her screams peaked and her pussy got warm and squeezed my finger. Suddenly a flow of warm fluid poured out into my mouth and was dripping off my chin. With her legs still shaking I got back on top and kissed her again meeting her smile.
She rolled on top of me and lifted up while reaching down to my huge boner and began squeezing it and rubbing it. "Now let me take care of you. Just relax." She began rubbing my abs and then put her hand down in my pants. Now her hand was directly touch my cock, and it felt amazing. Her hands were kind of cold. "Have I got you that hard?" she said as she stroked my dick all the way up while it was still in my pants. Her mouth soon followed her hand and now she had her face right in front of the bulge protruding from my pants.
"I have wanted to do this ever since I saw you get out of the pool." Kim said while still playing with my boner.
"Believe me, I have wanted to do this since the very first time I saw you at camp." This must have hit something because all of the sudden my pants were off and the only thing left on either of us were my boxers. She put her lips on the erected form through the fabric and began licking it. Even through the thin material I could feel her mouth on my cock. I was getting closer by the minute to explode, but I managed to hold it in.
Kim looked up at me and said, "I hope you like this, because I want to suck your cock so bad." Without hesitating, my boxers came off at her hands and my hard member bounced up right into her chin. Her eyes got big as she for the first time couldn't find her words. "You are 16?" I nodded. "I've been with a lot of guys Chris, but none have had a cock as big as you. I need it right now!" She licked the tip and swirled her tongue around it. Kim then settled her warm, wet tongue on the underside of my swollen head and licked so good. She then licked up and down the shaft. Both sides and then the bottom and then the top; her beautiful blue eyes glancing up at me. "Now sit back while I take your huge cock in my mouth." She opened her mouth to take the entire thing and she closed her lips around the head. I sat back and let out a groan and she pushed her mouth down onto the shaft. With my cock already wet from the saliva of her tongue she slipped right down. She pulled off and then went back on.
"Chris you are so big I love it," she said while spitting on my dick.
"Don't stop Kim you feel so good sucking my dick." She took the command and began sucking me some more. Up and down she went while slobbering all over the place. When she would look up into my eyes with my cock in her mouth, that's what really drove me wild. She then wrapped her hands behind my legs and she pushed all the way down until her lower lip was on my balls and her upper lip was at the base of my dick. I could feel it all the way down her throat and it was the best thing I had ever felt. She moved down to my balls and began sucking on them and licking them and it felt amazing too.
I put my hand on top of her head and guided her mouth back to my waiting erection. I eased it on and began moving her head at my pace as I used my hand to push her mouth on and off me. I pushed her all the way down until her throat was full with my entire cock and I felt my cum on the way. She gave it a few more sucks up and down before I said, "I'm gonna cum for you Kim."
"I want to feel your cum on my tits." she said as she put my dick in front of her nipples and began stroking as fast as she can. As the pressure built up in my balls and my cock, spurt after spurt of that warm cum exploded onto her tits. By the time I was empty her tits were completely covered in jizz and she loved it. Kim began rubbing it all over and then licked her fingers clean.
"I'm sorry I couldn't last any longer." I said with my head hanging.
"Oh honey we aren't done. You still have to fuck me. We still have all night and I expect to take full advantage of that. I'm going to go take a quick shower but when I come back I want to feel that huge, hard cock inside my tight little pussy." She gave me a quick kiss and walked to the shower. I watched her ass bounce as she walked away and I was shocked to see that I was already had a hard on again. Before too long she walked out still naked and used her finger to tell me to come to her.
I went over to her and we kissed once more before falling on the bed. She grabbed my still hard dick and stroked it a little. She got on her back, rubbed her pussy and said, "Fuck me with that huge cock and don't stop."
"I've never done this before," I replied.
"It's ok just do what you want to me as long as you give me an orgasm."
"Ok I've watched porn before so I will do my best." She giggled and laid back and spread her pussy lips for me to enter. I took the engorged head of my erection and rubbed her clit and down her pussy a few times so I could hear her moan again. I knew it was finally time to lose my virginity, but I never expected it to be to this sexy woman who was at least twice my age.
I finally took my dick and put the tip in between her lips and began pushing. All of the sudden she let out a scream as my thick head got all the way in her pussy but I knew by the look on her face that she wanted more. I pushed in more until I got about half my blood-filled erection inside her. I could feel her pussy stretching to let my dick in and then it closed around me and I could feel the muscles of her vagina squeezing my hard cock. "Fuck you are so tight," I said as I started slowly fucking her.
"Fuck you are so big," she quickly retorted.
I pushed in even further and then began going in and out while Kim began moaning.
"Oh Chris you are so big. Fuck me!" I went as deep as I could until I couldn't go any further and I felt her squirm and yell: "Ah it feels so good go faster!" Once again I obeyed and picked up my tempo. Her screams also picked up in pace as my dick was going all the way in and coming almost all the way out and I was going as fast as I could. Normally I would be taking it slowly to conserve my stamina, but after cumming less than 20 minutes ago I felt endurance I never had before. I went on for a little while longer before she wanted to change positions.
"Let my ride that giant pole of yours Chris." I couldn't say no even though the position we were in felt so good.
"Ok Kim get on top of my and sit on my cock," I tried to keep up with her dirty talk. She rolled me onto my back and crouched over my waist and started rubbing her ass and pussy over my stone-like penis. She finally reached back and grabbed my dick and rubbed her pussy with it like I did to her before, but now she was toying with me. She began sitting on it and I saw her face struggle to sit on the entire thing but when she finally did she let a scream slip and I could tell I would like this as well. I put my hands on her hips and helped her go up and down on me. She looked amazing as she was screaming and writhing in pleasure. Her tits were bouncing with her looking better than ever. She stopped bouncing and sat all the way down and started grinding her pussy on me and she was moaning like crazy. Our pelvic bones were pushing together and I could feel her little clit rubbing right above the base of my cock. She slowed down and said:
"Take me from behind Chris and fuck me as hard as you can. Make me squirt for you."
She got off and I grabbed her and bent her over the edge of the bed. I went straight to her pussy and shoved my throbbing member into her tight, waiting pussy. I gave her the best fucking as I went fast and deep, and her glass shattering screams proved that it felt good for her too.
"You want me to smack your ass?" I asked.
"Yes please spank me! And pull my hair hard!"
I never knew a mom could be so kinky but I didn't complain as I smacked her ass as hard as I could and I could tell it hurt. I smacked it again as she let out another shriek and I grabbed her hair and pulled her back by it. My hand had already made a print on her ass and now I was holding myself up by pulling her hair as I slammed her pussy from behind.
"Harder Chris! Harder!" was all I heard so I gave her everything I had and fucked her as hard as I could.
"I'm gonna cum!" Kim yelled, "don't stop!" I felt her pussy tighten all of the sudden and it got really warm. The next thing I knew, there was a stream of cum pouring out onto the bed and soaking my still pussy-submerged cock. This was all it took to put me over the edge so I followed right behind her:
"I'm about to cum where do you want it?"
"I want your hot load all over my face," she mumbled as she was still in shock from her orgasm.
I pulled out and put her on her knees right in front of me. I held her head by the hair on top and with my other hand I stroke my cock until wave after wave of hot cum shot onto her face. It lasted several seconds and she warmly welcomed my cum on her face. She sucked the little bit from my tip and then fell back.
"That was the best sex of my life. You need to come over more often."
She seemed to look even sexier with cum on every inch of her face. I laid next to her and I was so exhausted I was beginning to doze off. She got up to clean up and the next thing I remembered was waking up with her next to me in bed, both of us still naked.
We heard a knock at the door so we both scrambled to our feet to put some clothes on I managed to put on my shorts and a T-shirt but nothing else. She got a robe to cover her naked body and went to answer the door. It was Michael and his grandparents so I knew I had to leave. I snuck out the back door but not before stealing the underwear on her floor from the night before.
I got home and lied down to think about the best night of my life yet again. With my cock getting hard again, I rubbed one out once more, and went to sleep. The rest of the summer went on with quite frequent trips to Kim's house for more of the best sex in the world. I was now a man, and I had the chance to fuck the woman of my dreams and nothing could be better than that.