This is my second story; it is about a recent high school grad who gets a shopping trip from an older online friend.
I am a 26 year old single male somewhat heavy, but over 6 feet tall with wide shoulders. I am single and a little bit of a nerd, but I get by with a good income and have a good friends.
I have been searching online for a long time for a stranger to take lingerie shopping that will model wheat I buy and have fun with it. As I have talked to many women that would be interested it seems that most cases it is just a fantasy or they live to far away. Back in May I received an IM from a girl that claimed to be 18 and was about to graduate high school, her name was Jessica. For some reason that I couldn’t pick out this was different than most the IM’s I get on the subject.
Jessica the 18 year old brunette with beautiful brown eyes and a body that would have made any pro model jealous was not your usual internet girl. When Jessica first IM’ed me she admitted she only owned a few thongs and really didn’t even have any ‘pretty underwear’ as she put it. Jessica had admitted to having boyfriends on and off, and a few times in the past looking at porn and getting into the naughty chat rooms. She told me she always wanted to have some sexy underwear herself, but was too chicken to buy it and never really needed it having really only had oral sex a handful of times with boyfriends.
Even though we discussed the subject a number of times Jessica had refused to let me take her shopping. We did regularly trade back and forth links to lingerie sets that we liked, some very risky and others a bit more conservative. She had fun dreaming and I had fun helping. We wouldn’t always talk about sex and underwear, we chatted about school and everything under the sun. I gave her advice and told her of the things I regretted in my life. She would, well make me laugh and wish I was still that age.
The dirty chatting kinda left for a few weeks, and we still talked but the conversations weren’t as long, she was busy going through her graduation stuff with the partys and all that. Then one day I get an IM from her saying she wanted to chat and asked if I had a free hour or so. I of course said sure, it was a Monday night and I was only planning on going to bed early that night anyway. The next IM had her phone number it with the words ‘call me’. This was a new one to me, but nervously I picked up the phone and dialed.
Jessica answered and her voice was that of an angel. We chatted for about 10 minutes catching up how her graduation went and her prepping to go to school. Jessica finally stopped and asked a question in probably too serious of a tone, ‘Have you ever jerked off during our conversations?’ I admitted that I had and she said she had masturbated as well to the conversations. Then she confessed to still really wanting lingerie and also to really wanting to see me jerk off. I said that would be fun, and asked what she had in mind. Her response was “your fantasy” and the crickets chirped in the background as I was dumbfounded.
Jessica and I collected our selves and she gave me a time and place to meet her Saturday, she said don’t worry about anything. Well knowing I was meeting her on Saturday only left me with one issue… I relaly had to stop jerking it until then, just to make sure if anything actually happened I was up and ready with the load she wanted. The days at work I was day dreaming… so many times I wanted to back out but didn’t. I looked and looked trying to figure out what I wanted to get her, what might actually happen.
Then the day came, driving toward the coffee shop she wanted to meet at the butterflies in my stomach going nuts. I waiting in the car as I was early and was checking my breath making sure I didn’t smell, wishing I could have a smoke and not smell… Then as I got out of my car I see the old VW with the graduation tassel in the rearview mirror and what looks to a be a beautiful young woman getting out. The pictures didn’t lie, this beautiful girl in a very nice white sundress smiles at me and shyly says hi. As Jessica walked towards me I reach out my hand to shake hers. Jessica brushes by my hand and gives me a big warm hug, whispering into my ear “It’s so nice to finally meet you!”
The smell of her hair and the warmth of her hug made me think I may be in heaven. As we pulled away, she suggested we get something to drink and relax for a few minutes. We chatted about all sorts of things, until I finally let out that she had made trying to concentrate at work a living hell for me for the last week, she quickly responded with her confession of anticipation and nervousness. As we finished our coffee I asked her what her plan was. With a smile she replied she would tell me while we walked to the mall (we were already in the mall parking lot).
Jessica told me she wanted me to buy her a few things from a few shops in the mall, promised it wouldn’t be much and asked if that would be alright. I agreed and said it wasn’t a problem. She then explained that she wanted me to come with her after the mall as she was house sitting for a cousin of hers. She admitted ahead of time that at the house it would be her rules or I would never get to see her again. She knew I had no problem with being teased and the woman taking a control from our earlier conversations.
At the mall Jessica dragged me to a few lingerie stores and picked out a number of things, holding them up for me to see. At first she had picked out two very sexy bra/panty sets, one was all lace with a thong, the other was silk or satin with boy shorts. I bought those two sets thinking I had made out alright and then she was leading me to a store that was a little more smutty and she picked out a mesh halfslip with garters, matching silk thong and a mesh bra, she also got the thigh highs for the garters. She knew I was going nuts now. I bought her the set with a big smile on my face. I think she was as excited as I was, she practically skipped back to our cars, we decided to take her car back to her cousins house.
Once we were in the house Jessica got a few glasses of ice water ready and asked me to follow her. She led me to the second floor that was one giant bedroom with a large bathroom. When we got up there she said “once I go into the bathroom I want you to strip and sit in the middle of that couch.” I just smiled and said ok. The anticipation was killing me, I don’t know that my hard on had gone down since we got to the mall.
So there I am sitting on this leather couch naked waiting for what seemed like hours but was only a few minutes. Jessica sticks her head out and with a smile, says “good, are you ready to see what you bought me?” I say yes with maybe a little too much excitement, but don’t really care. Jessica steps out of the bathroom in heels, her new black silk boy short and matching bra… those legs, firm stomach and great D tits, oh the things I wanted to do to her. Jessica was trying very hard to be confident as I think she has never been this open with a man. As she walks in my direction she flips on music and smiles at me. Standing at my feet she gives a bit of a twirl and asks if I like. Well I nodded saying very much so, but my raging hard on I am sure confirmed it.
Smiling at me she said “you have been so good all day, but I don’t want you to touch your cock until I tell you too ok?” after I nod in agreement, she continues “Now I want to give you a lap dance, keep your hands to yourself or only where I put them ok?” again I nod. Jessica turns around and begins swinging her ass toward me. Oh what a beautiful sight, she backs up leaning her silk covered ass against my chest, rubbing up and down getting lower and lower. I feel my tip rub against her silk material, Jessica moans and pushes into for just a second before she gets up. She is now facing me, standing in front of me, legs spread she kneels down straddling me on the couch, he silk covered pussy just inches from my cock, her knees on either side of me. She puts her hands on my hips as she leans back giving me a great view up her body. As she leaned back up she held my hands sliding them up her stomach to her bra letting me hold on and feel for just a few moments. As my hands reached her shoulders she guided both of them to the couch on either side of me. Jessica sat up and pulled my head in to her chest, kissing me on the top of my head and with kisses making her way down to my lips as she lowered her self down. I begin to feel her boy shorts rub against my hard on as she kissed me on the lips. It wasn’t long before we were getting passionate kissing and she put my hands on her ass. Her hips were moving rubbing that silk material against my hard on.
I was in heaven, just as I started to get close and her moans started to get louder, she stopped kissing me and got up. Jessica walked to the bathroom slowly saying “I take it you really like the first set. Remember no touching unless I say.” With that the bathroom door shuts and I am left with a cock leaking precum. A few minutes later Jessica walks out of the bathroom with the red thong and bra on. Her smile is brighter and confidence is definitely up. She walks toward me holding the black bra and panties, tossing them on the couch next to me, she says “stay there and give me just one second.” She walked over and opened a closet door, I wasn’t sure what she was doing until I saw my reflection in the mirror. My focus went back to her beautiful ass and body.
Jessica sat down in my lap with her back to me, she quickly scooted back until my precum covered cock was nicely nestled between her perfect ass cheeks. Jessica then spread her legs as far as she could while her feet were still touching the floor. Her hand reached between her legs and I felt her rub my balls and when I looked up I could see in the mirror her hand rubbing her pussy through her thong. Her hips began to move and I could see her hand now inside her thong as her ass moved against my still raging hard on. Using her free hand she took one of my hands and put it over her thong on top of the hand that was slamming 2 fingers in and out of her pussy, she placed my other hand on lace covered chest.
As Jessica moaned I begin bucking my hips more and more, my fingers twisting and playing with her nipple through the thin silk material. I know I was beging to get close again with her ass working wonders. As she brought herself through a few orgasm I was beginning to get really close, and her ass had done a great job. Soon enough she stood up and handed me the black bra on the couch next to her and asked me to cum in it. I took the bra from her hand placed it over my cock rubbing it hard. Jessica smiled and as I looked up at her I could see the thong out of place and had my first glimpse of her bare freshly shaven pussy. After she followed my eyes she smiled.
Jessica said “here this may help” as she pulled the thong completely to the side exposing her aroused slit, then pulling her tits out of their captivity. As if this wasn’t enough her fingers that had been pounding her pussy were put under my nose and then into my mouth. I blew my load as I sucked on her fingers. I definitely had a huge load in her bra and I used the bra to clean up. As I slouched back on the couch, my 18 year old dream kneeled before me and licked my cock clean.
Jessica smiled and walked over to get a glass of water, handing it to me with her tits and pussy still on display. She smiled and said “I hope that boy has some more energy left in him” patting my cock “there is still a grand finale to cum.” Jessica then walked back to the bathroom.
I sat on the couch knowing what she was putting on, and thinking it was still taking her a while, but was greatful for the recovery time. I was still half soft when Jessica came out in her last outfit. But it didn’t take long to get myself back to full mast, her legs looked so good in the thigh highs, and the black mesh half slip was such a great tease, her nips were still hard and so nicely poking through her mesh bra. As she got closer and my eyes darted up and down taking in the beauty, I realized it was a front clip bra which was even better. Jessica looked at my again hard cock “Glad you are ready for another round.”
Jessica then stood on the couch feet on either side of me, I looked up and saw the black thong we bought wasn’t there and she held my head back as she lowered her pussy to my mouth. What a beautiful sight as I licked and suck on her for everything I was worth back and forth from her clit to her tunnel, my tongue going nuts sucking her clit into my mouth and flicking it with my tongue like a fest snake. After she had covered my face in pussy juice and damn near pulled my hair out, she got off the couch and set on the edge of the bed. With an evil smile she said “come stand in front of me.”
As I complied, she took my cock into her mouth and get me really going again. Without warning she stopped and laid back on the bed. Jessica smiled at me as she unclipped her bra and told me to straddle her chest. As her nipples came into view, my cock was nestling itself between her mounds. Jessica pushed her tits together and smiled up at me saying “titty fuck me.” I began slamming my cock and enjoying the feeling her tongue out, taking some precum from time to time. We both smiled as we watched my cock go in and out of the tunnel between her tits.
As I love titty fucking I was in heaven, until she stopped me. Jessica said she wanted to see me jerk off for her, but this time she wanted me to be standing over her and to shoot the cum on her. I agreed and stood between her legs while the dangled off the edge of the bed, she spread them giving me a great view of her wet pussy and forcing that mesh half slip up her thighs, pulling the thigh highs tight. As I began to stroke my cock for her I noticed the glisten on her tits from my precum, I noticed how wet her pussy was, her hips were moving without her even touching herself. Before long I was watching her finger herself and she was moaning dirty things. She told me how bad she wanted my cum on her, how she had fingered herself so many times thinking of this, how much she loved my cock, how wet her pussy was, how hard her nips were. She screamed and actually squirted a little bit, her hips bucking as I stroked my cock and when I saw that little squirt, that was all it took for my cum to let loose. From her chest, to her stomach and even a good amount dripped out on to her half slip, cum was everywhere.
That was great I thought to myself, looking at my work and thinking of its beauty. We cleaned up and got dressed. Before we walked out to the car grabbed her from behind, my hands on her stomach and held her back to me, kissing her neck and ear as my hands roamed the front of her body, I whispered into her ear a simple thank you. Jessica turned around and kissed me passionately as she held me in her embrace.
Jessica dropped me by my car at the mall and before I got out, she said “call me, we need to do this again, maybe even more fun next time.”