Her First Time, Like It Or Not


Tom and I had been good friends since college. He had married a really hot girl, Beth, that I had a hard time not lusting over. Alright, I had tried to sneak a few peaks of her naked when we vacationed together, but unfortunately always failed. The years went by and they quickly had two daughters, while I stayed single. His oldest daughter, who had turned 18 in June, was named Molly.
Molly always had a slender build and was average height, I am guessing about 5 foot 4 inches. At her 18 th party I noticed she was starting to develop, probably up to a solid A cup, if not a small B cup. She still had a slender build, but with her very tiny waist could not help noticing that she had the hour glass figure well on its way.  Molly and I always got along well. The fact that I had a ski boat and would have her family down for weekends at my cottage and take them all water skiing did not hurt. While her parents were relatively strict with her and treated her like a little kid I tried to build her up and complement her on her beauty. With her light brown hair, big blue eyes and cute body the compliments were not fake.
It was during one of these planned weekends at the lake cottage that Molly and I unexpected spent some time alone. Molly had been at cheerleading camp all week near my lake cottage and I volunteered to pick her up that afternoon and take her to the cottage, since Tom had to work a full day and then go home to pick up the rest of his family. Even though I was in my early thirties the thought of stopping by a teen age cheerleading camp and then spending an hour in a car with Molly was pretty enticing.  I was on my way to pick up Molly when I recieved a cell phone call from her mother Beth.

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   It ends up Molly's little sister had try outs for a play she really wanted to be in the next morning so they could not make it to the cottage until noon on Saturday. She apologized and offered to drive out that night to get Molly. I told her not to bother, that I would just take Molly straight to their place or Molly could just spend the night. Beth said she did not want to inconvenienceme and I said it was zero inconvenience since I was just planning to do some work on the cottage and the boat. We agreed to leave it up to Molly and touch base after I picked her up.
The cheerleading camp was as much fun as  I thought it would be. I was early, as planned, and there were babes everywhere. The camp was for high school age cheerleaders, and some of the older girls looked like they could be LA Laker dancers. Some of the girls were really built, and I was thinking they must really bounce when they jump. Found Molly and she gave me a big welcome hug, which I made sure to extend by pulling her tight. Helped her load her stuff and noticed her body looked ever tighter after a week of working hard at the camp. Her blue eyes really stood out as her skin bronzed from being in the sun.
As we were pulling out I gave her the news about her families delay and gave her her options, drive two hours back home or drive a half hour to the cottage and go water skiing. Wanted to frame the question right and it worked. After she gave me the no duh look she called her mom and told her she wanted to go to the cottage.

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   I over heard her mother tell her to make sure she helped me in cleaning the cottage and boat.  
We arrived at the cottage and it was in great shape, after my sisters fmily hd borrowed it the week before. The boat though definitely needed cleaning, after sitting on a trailer for the last month. Molly said she would clean it, but I told her I could not let her do it alone. She then realized that she was without a bathing suit, in that her mother was suppose to bring one for her. After a few dirty thoughts of thinking of telling her she could go without I remembered that my sister kept a suit at the cottage. I gave Molly the suit and a safety pin, since my sister, while thin, was bigger than Molly. Molly came out in the bikinitop and with her cheer shorts on over the bikini bottoms. She grabbed a sponge and asked where to start. My sick mind told her it would be easiest for her to start on the outside of the boat, since she could stand up while working. I told her I would work along with her from the inside of the boat reaching down to the areas she could not reach. While she thought I was being nice, I knew I was just being a pervert in that I knew with this arrangement I would be forced to be looking down at her beautiful hard body the whole time we worked. I wondered if other people my age were anywhere as close to being this sick, in that Molly was only 18 and I am in my mid thirties.  But at that point I did not care, she looked great and I was rock hard. We begin working and with a fringe benefit of the too large bikini top was that it would just hang open when she bent forward to get more water on her sponge.

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   She would often try to hold her top to her breasts when she would bend over, but with a sponge in one hand and her other hand all wet she would often fail and it made for a great show. It was interesting, with a bra on Mollys breast looked small and round, but when hanging loose they looked like small pyramids, sticking straight out. Her nipples were lightly colored and also seemed to be sticking out hard. I was thinking maybe it was from the cold hose water, since the temperature was only in the sevnties. We had only been at the cottage and hour and  I could not believe I had seen Molly's beautiful breast, even if she was trying to hide them. Never enjoyed cleaning the boat more and was sad when we were done, thinking it might be the last time I ever see breasts that young and perfect.
Told Molly I felt bad making her work that hard and offered to let her water ski. She jumped at the chance and I let her ski until she was exhausted. She usually has just a short term, since there were always others waiting and she could not believe I kept letting her go again after she would fall. The highlight for me was holding the ladder in place as she climbed on board after her last ride. She was worn out and it was a struggle to pull herself up the ladder. The bikini bottom had strtched a bit after getting wet and the safety pin did not stop it from sliding a few inches down her butt as she climbed out. What a sight, that beautiful white tight butt, just below the dark tan line. Could have looked forever, but seeing that she was struggling had to move around to her front to help pull her out.
Went back to the house and both showered and got dressed for dinner.

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   I grabbed a beer and she was having a lemonade. I mentioned how beautiful she was and asked if she was dating. She mentioned that she was not allowed to date until she was 18 I asked if she ever had a boyfriend and she said no. She said her friends had told her about boys that liked her, but between going to a catholic grade school and her parents she really hadn't had a chance. I told her that would change quickly now that she was going into high school and that I would have asked her out in a second. She giggled and said she was a bit afraid of the whole dating thing, since she had zero experience. Joking around I said I would be her boyfriend that night at dinner, so that she would be at least a little prepared. She looked at me and said that would be fun. I said "ok, but this is just betwen you and I. And don't make fun of me if I stutter, because I am not used to such a beautiful girlfriend. " She punched me in the arm and said to quit teasing and I responded that I was not teasing. Molly left to grab a sweater, I ws hoping she would not put it on ver her tank top and skirt.   I grabbed another beer and a lemonade for Molly. This is where I really began to cross the line. I put extra dry lemonade mix in Molly's glass and a shot of vodka.

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   Don't really know what I was thinking, but thought it would make things interesting. Also put another show of vodka in a zip lock bag in my pocked. I knew what I was doing was waywrong, but ever since seeing those breasts dangling I was thinking all day with the wrong head. Molly returned and I toasted the new couple. I told her I would treat her like a girlfriend and show her the things boys would try on dates. I said boys would probably try to move things along faste than her and she needed to be ready and figure out how she would respond. I repeated that this was favor to her and that it was just between us and she said of course.   We finished out "cocktails" and I grabbed her hand for the walk to the car, it felt so smooth and small.
The restaurant was very nice, with a nice table over looking the water. We sat next too each other facing the water. Molly was very talkative and relaxed, I think her first shot of alcohol had her initially flying. When she left the table to visit the rest room I snuck a secong vodka shot into her drink, and decided that was enough if not too much. When she came back I told her she would be pretty safe in a restaurant, but in a secluded table like this a boy might let his hands wander. She looked at me like "what are you talking about". I said they might put their hands on her beautiful leg and just hold it our slide there hands up and down like this and showed her with my hand just above her knee.

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   She said "that does not seem to be too bad". I said it is not, but with her wearing a short skirt thay might try to push it a little further and slide their hands up her skirt a little and I then slid my hand a lttle under her skirt and massaged a ways up her thigh before pulling out (boy did she feel great). She said why would they do that. I could tell she was not playing dumb, so I slowly described the steps boys might take using the old baseball analogy. First base = kiss, second base = touching breasts. . . I used very tame language and said it was awkward to discuss but she should know what her friends are talking about and how boys think. Don't know if she bought it all. At this point dinner was over and it was time to head home.
On the drive home I mentioned that dates often consisted of a dinner and movies, and we could watch a movie at my house. Molly said she was game.   We got home and I said Molly could pick a movie. She was looking at an r rated movie and said it looked good but her parents would never let her watch it. I said go ahead, since I knew it had a few very sensuous scenes.

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   We sat down on the couch and pulled her over to me and wrapped an arm around her shoulder and told her that is how dates often sit. I looked down at her beautiful eyes and they were glassy and she said she was feeling tired, probably the effect of the vodka. I told her to just rest her head on my shoulder and relax. After a few minutes of the movie I told her this was probably the first move many boys would take and I moved my right hand down from her shoulder to the closest breast and gave it a nice soft squeeze and started to grab a feel (they were small, but as firm as my imagition had thought). She then pushed my hand a way. I told her that was the perfect response, that with her looks boys would want to grab a feel and she would have to decide when she was ready. I asked her how it felt "good, bad. . . ", and she said it just felt weird. So much for my ability to turn on a fourteen year old.
I then said at this point boys would often try to go for a kiss.   I asked her if she had ever kissed before and she said only relatives. I aksed her to show me and she gave me a peak on the cheek. I told her boys would want it longer on the mouth and she gave me a longer closed mouth peck on lips.

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   I then gave her an explanation of the different types of kissing, from pecks on the hand to deep french kissing (DFK) with tongue play. I told her to save the DFK kissing for a boy she really liked, but that she should really practice before that time. I said lets try it real slowly and at least you will know what to do. She gave me a doubtful look but softly said ok, perhaps the vodka was helping me. We started lightly kissing, with her mouth open about 1/16 of an inch. I explained that was not quite it and told her to kep her lips loose and  Iwould show her. I slowly pushed her lips open with my tongu and tried to be very gentle and slow, so that she did not get spooked. I genlty kissed her top and loer lips, htey were s soft. She felt great, but there was little coming back. I then explained that she would need to kiss back more, but that it would be easier with a real boyfriend.
I told Molly there was one more of my favorite moves that boys would often try while kissing. I told her that while kissing boys would often let there hands wander, usually to feel a breast like I showed her earlier. I said that when boys did that they would often try for more that just a quick feel through a shirt. I said let me show you and I gently kissed her on the lips and touched her breasts through her short for a split second.  I stopped kissing and said that was one way.

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   I then said let me quickly show you the second and third ways. I gently kissed her and this time slid my hand quickly under her tank top and lightly touched her bra and quickly pulled out. I did not want to spook her any worse and really wanted to show her the third way. At this point I was one step beyond hard and could fel some pre cum wetness in my pants. I was so exited I was in pain. I knew I had pushed our little game as far as Molly wanted and could tell by her eyes that she was not interested in going any further, but I also knew I could not stop with a quick touch of her breasts thru a shirt at this point. I then said "ok Molly, that is about it. The last thing I will show you is the third method boys will take when trying to feel a girl up".   I started lightly kissing Molly again, but this time pushed it a little more and had her head backed uop the seat cushion.   I then quickly slid my hand up her shirt and felt her body stiffen. I knew this was my last shot, so instead of just trying to slide my hand under her bra I pushed it up over her one breast. Luckily her breasts are relatively small and the bra pushed up rather easily. I grabbed her breast between my thumb and fingers and gently massaged. At this point she tried to push my hand away but I kept enjoying the feel of her firm, but soft, breast. She tried to break our kiss off, but I kept kissing her, holding her head in place with my other hand, even as she tried to close her mouth.

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   Perhaps I was thinking she never said no, so as long as we were kissing I had the go ahead. Her little tit felt great and I kept massaging it even as she was now trying to slide out from under me. I quickly rolled on top of her on the couch, putting my leg between her legs so that she could not slide out. I began to tweak her nipple, thinking it would get hard quick, but it took a while to get it as hard at it looked when we were washing the boat. Now my rock hard cock was resting on her thigh, and her squirming around was grinding it even through my pants. I now reached across and grabbed her other breast, it felt as great as the first. Molly was struggling to break off contact anyway she could, but 100 pounds is no match for 190 pounds, especially when that person is more sexual excited that he has ever been.
I need to taste the most beautiful breast I had ever seen, and have now touched. I slide down to kiss Molly's breasts, my waste now between her legs, pinning her down. As soon as I break the kiss, Molly starts screaminh "stop, what are you doing, no. . . . . ".


   I push up her shirt and look at her great little breast and start sucking on the right breast. I can get the whole breast in my mouth, and twirl my tongue around her nipple. I have to suck hard and hold her with both hands to keep contact. I am  thinking this must feel good to her, my girlfriends love this move, but the screaming reminds me that she does not enjoy it in the least. I normally could do this for a long time, but not in these conditions. I move back up and start kissing Molly again. Her mouth is closed, but I force it open with my tongue.   I am surprised I can get my tongue in her mouth and it is a lot nicer without the noise. My left hand quickly moves from the back of her head to her thigh. Molly's short skirt has ben pushed up already so it is real easy to reach the front of her panties. I start massaging her opening through the panties. Molly is trying to move away in every direction, but between my legs and arms I have her very securely positioned. Molly is not wet at all through her panties, which reminds me how far I have crossed the line and how different this is from all my previous recipricol sexual escapades.  I move my index finger to one of Molly's thin long legs and slip it under her panty, I start moving around and find soft thin hair covering her mound.   It takes a little while, but I find her opening.

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   It is not very wet either. I genly massage all around the opening, paying extra soft attention to her clit. I am thinking she must find this enjoyable, but i open my eyes and can tell by the shock and teror in her eyes that this is only feeling good to me.
For the 20th time that night I think of stopping, knowing I should, but I am now out of my mind. My hand pulls away from her warm box, but instead of stopping reaches for my zipper. I don't even thinking of stripping our clothes off, I need to be inside of Molly now! I get my zipper down quickly, but with one hand it takes a while to get my rock hard boner through my boxers. It is so hard and hot the fresh air feels good on my cock. I am almost seven inches long, but pretty thin. I remember thinking at the time that being thin was probably good for a change.   I now reach again with a few fingers under Molly's panties. I slowly massage her opening again, but this time try to slide a finger a little inside her. I finally find the exact opening and try to push my index finger in. It slides in a little, but even trying to slide in a little is really tight. I push it up and down just an inch or so and it feels like her body is being lifted up by my finger her pussy is so tight. I know move my cock near her opening, keeping my index finger in as a placeholder.

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   When  Iam in my other fingers of the same hand are holfing my cock next to my index figer. At this pint Ibreak off the kiss, because I want to give the next move all my attention. Molly is now really screaming "No, please stop. Anything, but this. . . " But it is this or nothing for me.   I slowly start to pull out my finger and try to push my cock head in.   It does not go in at all. Did I slide away from the opening? I reach down and push in my finger - no, still got the right spot. Now I push my cock head hard and it goes in a little, which brings a huge scream from Molly. I am wondering if I am going to get all the way in and whether I am going to  explode before getting there. I begin to lightly push in and out slowly working the head in, to more screams from Molly. It is now firmly in and I run into the hard barrier I knew I would find. I feel real guilty at this point, but know I  can't stop.

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   I give it a few hard pushes and break through, to an ear splitting scream from Molly. I am now most of the way in and want to be all the way in.  I continue with slow but firm pistoning and make it all the way. I am surprised, her pussy is so tight it feels like my cock is sliding between hard bones. It is not the wet sloppy sliding in and out, but instead sliding a little in either direction causes a lot of friction and almost pain to my cock. I have only been inside Molly for about a minute or so, but am about to erupt. Decide to push all the way in and rest in her warm hole, so that what may be my last fuck as a free man will last a little longer. Molly is now just moaning under me.   I get all the way and think I am  going to just enjoy being inside Molly. But her pussy is alive, contracting around my cock, she is also moving underneath me, causing more friction. I think for a split second she is begin to enjoy this, but I open my eyes and she that she is in pain and is just trying to slide me out of her. I realize  I am not going to last much longer and give it a few nice long thrusts before pulling out and shooting the biggest load of my life on her stomach and chest.
It felt great as it kept shooting out and out. But immediately I look at Molly and think what  have  I done. Even crying she is beautiful and now has cum on her dark tanned stomach and bright white tits.

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   The look in her eyes tells me I will pay for this. I had never experienced anything that felt better than the last five minutes, but I will have to tell you when I get out in twenty years if it was worth it.



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