My First Time 271

A Shy Teens Very First Time

The following is a true story with just the names changed. This takes place in a little town in Western Massachusetts where I lived at the time. I was in high school and just turned 19 in my senior year.

I was very, very shy while growing up. I didn't really expand my friends much in high school. I was super quiet and extremely shy. I barely spoke to any girls, except for one. She was in my Temple USY (Jewish religious youth group) and a little younger than me at 18.

Somehow we became close friends and spoke almost daily on the phone. We would talk after school most days. She was also dating my best friend. So I'd see her over his house and at USY activities. Somehow, squishing next to her in car pools. She'd whisper something in my ear on those and get me smiling and I'd shush her so her boy friend Howie didn't catch on. Her name was Cary and she was a 5 foot cute girl with dark shoulder length hair, big eyes, really cute face and body and huge boobs. I was more interested in her older sister who was a year older than me and was more petite as big boobs were not my thing. But Howie was entranced by them. He spoke about those huge boobs all the time, more than the person inside. And Cary knew that, but still stayed with him.

And so it went with Howie telling me he was dieing to get in her shirt and pants and she was going to be his first. Then with Cary talking to me at other times telling me what Howie wanted to do to her and how she wasn't ready and he was pushing her. Then she told me she went on the pill with her mothers permission to be extra safe even though a condom was going to be used.

Nothing happened between them yet. Howie had been pushing for about 2 months and was getting aggravated in his wait. Time was passing. Soon enough I told Cary.

I was going to have the house to myself from Friday afternoon through Sunday late afternoon on a September weekend. My parents were taking my sister to a friends in Salem for the weekend and they were spending the weekend in Rockport. The house was mine to relax in. I only told Cary. I wasn't a partier, which my parents knew, so they weren't worried about that and they left me the other car as I had earned my drivers license a few months prior.

Cary suddenly loved the idea I was going to be alone and wanted to join me for the weekend. I said no as Howie would kill me. But she concocted a plan with a girlfriend of hers a few streets away. Before I knew what was going on, she was ringing the doorbell with a duffle bag of clothes in her hand. I let her in and she grabbed me in a big hug. OK, this was getting interesting. I was kind of shocked by the hug, but gently hugged her back. Having her so close to me gave me an instant erection that I hoped she did not detect. Her first words to me were "I'm starving, what's for dinner?"

I ordered a pizza and it was delivered and I paid the driver and gave a tip. I had been cutting lawns and doing odd jobs and had money and always paid my own way. Cary's family was wealthy (by my standards) and she didn't work other than the odd baby sitting job, and had a nice allowance each week. While waiting for the pizza, I showed her my sisters room and put her bag in it. She went up and changed into pj's and came back down. I had to admit, she looked good and snugly. She told me to go up and change into my pj's which I did. We made sure she was not visible when the pizza came as I knew the delivery person.

The pizza was consumed and we went and watched TV. This was before cable and only had over the air TV or VHS movies. We watched whatever was on. I sat in my usual spot on the couch and much to my extreme surprise, Cary set right next to me. And we started chatting, just like we always did on the phone, but in person. Talking about everything we always did. Only this time she told me how she took Howie's "thing" in her mouth and it exploded. She gave me much more detail than I ever would have wanted and was very thankful it was dark in the room so she could not see the tent in my pj's. Or so I hoped at least.

I remember vividly how she told me she was on her knees, just wearing her bra and how she was touching and feeling him and how hard he was. How she stuck her tongue out and licked him as he was drooling. She said he was salty. I kept saying I do not want to hear this. But she went on anyways.

She told me she licked her lips to make them wet and soft. I said commented they were probably always soft. She shushed me and kind of turned in to me and laid her hands on my thigh, leaning more on to me and was whispering in my ear. I could feel her hot breath near my ear and felt like I was in an immovable trance. Frozen in place. Thinking back, if I hadn't been so shy and scared, I probably would have attacked her screwing her like crazy. But, I was frozen in place, just trying to breath and glue to her every word.

So she started again, telling me again how she got her lips nice and wet and placed them over the tip slowly. Moving her mouth up and down and using her tongue on the underside of his thing. At that point I remember laughing saying can't you call it something else? She said what and I listed off a few suggestions and she chose dick. And then started again saying she was slowly going up and down on his dick. Feeling every part of the underside on her tongue and feeling it get bigger. Cary then said she was holding his balls in her other hand and they were getting tighter. She then said she pulled back until just the head was in her mouth and she was tonging the top and it exploded.

At that point her hand moved and bumped my dick, which was like a flag pole. I think that surprised her as her eyes got real big and she looked at me. I was looking at her looking at me, not knowing what to say or do.

She told me she pulled him out and he was spurting on her tits and bra until he finally stopped. She said he tasted salty again and got soft. She said she held him gently and licked and cleaned him off. I asked her how she knew what to do and her older sister had told her and said her sister had read it in a magazine. She then shifted even more against me and the back of her hand was pushing against the side of my dick. I was afraid to move. She had this smile on her face.

Cary then said that Howe got down on the floor and removed her bra and started feeling and playing with her tits. I felt those tits pushing into my side. She said he was rough and hurt her a little bit which took her out of the mood even though Howie was hoping to screw her that day, she said no and ended his fun right there.

Where as I was there listening and knew some of it as Howie gave me the broad details. She knew I knew and I'm pretty sure was enjoying the torture she was doing to me. She then leaned a bit more, pushing more against my hard dick and whispered in my ear that she doesn't want Howie to be her first. This surprised innocent me. And she then learned more in to me and planted a small kiss on my lips. I was frozen in place but somehow breathing. That first kiss turned in to a 2nd and in to a 3rd. By the time of the 3rd, I was starting to kiss her back and she had this big smile on her face. She put her hand on my chest above my heart and asked why it was beating so fast. I just raised my eyebrows and looked at her and she laughed.

She by now was sitting in my lap, boner under her but pushed down a bit. But still rock hard. We kissed a few more times and I was getting the hang of it and enjoying it immensely. She knew she was the first girl I had kissed.

The sweet and soft lips, the sweet smell of her hair and body. I commented how she smelled so nice. She liked that and wiggled her butt on me. I was worried I was going to explode right under her. She kissed me again, this time exploring with her tongue which met my tongue and we played like that for a while and slowly she just laid against me and whispered in my ear how she liked this so much. That this is the way it is supposed to be. I think I agreed and was loving every minute of it.

The news came on and we decided to call it a night and shut off the TV and go up to the bedrooms. I was looking forward to jerking off, probably a few times before I would be able to get to sleep. Wondering if I even could, while Cary slept in the next bedroom.

But it didn't work out that way. I decided to sleep in my underwear and crawled into bed. I was thinking about what had just happened when Cary walked in and asked if she could join me in my bed. I don't think I got a word out before she lifted the covers and slid in next to me. I put my arm out and she laid on it and slid in close. I think she had a big t-shirt on and wasn't sure of what else if anything.

She snuggled in closer and laid her head on my chest and made little happy sounds. I laid there wise awake. I LOVED the feeling of her body on mine but was wide awake and knew there was no possible way for me to sleep with her this close. I didn't care as she felt so nice!

After a few minutes Cary said she was so nice and comfy, she thought we could stay in bed all weekend and I agreed. She then adjusted her body and leaned over and started kissing me again. I figured with her beside me, she wouldn't feel my boner. But I was wrong as she slid on top of me and straddled me. There was no way she didn't feel me and I was wearing boxers which did nothing to hide my predicament.

There was little light in the room so I couldn't see her. She must have been thinking the same thing as she reached over and snapped the shade which let in some moon light. I stated she looked very beautiful as I held her head in my hands and she bent down and kissed me again. Then she got this mischievous look on her face.

Cary then slid down me a little until she was resting her head briefly on my chest. Then she slid further down and was licking my belly button which I found to be extremely stimulating and a little ticklish. She then slid further down and rested her head at the top of my boxers with my dick barely below her chin. My legs were splayed as she was between them.

She slid lower and placed her hands on my rock hard dick. I was watching her with wide eyes afraid to move. She gave me a little squeeze and I think I moaned. Cary then hooked her thumbs into the waist band and pulled down my boxers, pushing my legs together until they were completely off and tossed them off the bed. I was still laying there wide eyed afraid to move. She then pulled my legs apart and climbed back up me a little bit.

Cary then leaned over and licked the tip of my dick. I was drooling pre come quite a bit. She then leaned down and took a bigger lick and looked up at me with a big smile on her face. I was still looking at her. With her eyes locked on mine, she put my dick in her mouth and slowly licked me up and down. OMG, it was indescribable. So soft and warm and wet. She came up and asked if I liked that to which I shook my head yes. She played with me and said she didn't hear me and I squeaked out a yes. She asked if she should continue and I think I said god yes, please. So down she went and then up and down. Then she stopped and just very slowly and gently licked me and I groaned and moaned. She licked the tip and I groaned and then around the head, taking it into her mouth and licking gently and I groaned louder.

Cary then lifted up and told me to come in her mouth when I was ready. She then licked the tip again and went down on me much further and I came. It felt like gallons. My eyes closed, my back arched and I came and came. Finally I think I stopped. I was sweating and panting. Cary produced a towel from some where and wiped off her face what she had not swallowed. She came up and rested her head on my chest and told me that was very nice and that I tasted pretty good. She told me she was honored to be the first to give me a blow job. She then reached down to my now limp dick and laid her hand on it. I seemed to have recovered and started to grow again. Cary looked at me, eyebrows raised and smiled again. I said sorry, I couldn't help it. She said she was honored and slid back down me again. I said wait, but she didn't.

This time she engulfed me and bobbed up and down much more quickly and I was rock hard again. She then started using her tongue on me again, licking softly then a little more aggressively and I started moaning again. She was holding my balls and squeezing them a little bit. And going from bobbing up and down to gently licking me while watching my face and eyes. She must have felt something as she took much of me in to her mouth and I came again. It only felt like a little bit, but was enough. She swallowed and no towel needed this time. Cary then crawled back up on me, put her head on my chest and hand over my dick. It stayed down. She pulled the sheets up over us. Had my arm around her and think I passed out.

Somewhere in the middle of the night, hours later I awoke and wasn't sure where I was or who was with me. I very quickly remembered and lay on my left side with my arm on Cary's butt. She was on her stomach.

I started gently rubbing her back and butt as the shirt had bunched up near her shoulders. I stroked down her leg up her thighs which were very soft onto her butt and then her back. Slowly and quietly a gradual moan came from her. So I continued, but more caressing now. I was amazed at how soft her thighs were and she spread her legs giving me access the insides of her thighs which were even softer. My boner had returned and I ignored it, paying attention to Cary.

Gradually I was kneading her butt and thighs and touched her and she was damp. So I included that area in my touching and her moans let me know when I was doing something right. Eventually as I explored more Cary started moaning and moving more and urging me on until she arched her back and let out a big moan and then slumped down and told me to stop. I waited to say anything and she snuggled in next to me and kissed me tenderly and said that was VERY nice, but could we go to sleep now? Sheepishly I said yes and we curled up against one another and fell asleep again.

I awoke with the sun streaming in having no idea what time it was. Cary was watching me with a smile on her face. I asked what time it was and she said a little after 11 am. I suddenly realized I was quite hungry and asked if she was and she was.

I made some bagels and eggs and we both ate heartily. I decided I wanted to shower and Cary said that was a good idea. I said she could go first and she said uh uh. Why I asked and she said together to which I think I blushed and she laughed.

Into the shower we went. Again the kissing started and we both seemed to love how tender we were, at least at the start. Then we soaped up and started touching each other all over, washing and touching and looking at each other. When she washed my dick last and I was hard, she just looked up at me with raised eyebrows tow which I shrugged.

I washed her bottom to top taking special care at her boobs. She knows I'm not a big boob guy but she said she liked the attention I gave hers. We dried off and decided to stay in pj's all day and watch TV. My parents called mid afternoon to check on me and when Cary figured out who I was talking to, she started playing with my dick. No fair as I couldn't acknowledge her and made talking to my parents difficult which she found extremely amusing. My parents told me they were staying thru dinner Sunday and would probably be home around 8pm. When I hung up, I told Cary and she smiled the big smile. I asked if she needed to call her parents and she said she would check in with them around dinner time. This was before caller ID so calling from my phone was safe from being discovered by her parents.

We spent the afternoon snuggled on the couch watching TV. I made burgers on the grill that night and we ended up back on the couch afterwards watching TV again. Cary said she was hot and took off her bottoms. Seeing her legs and thighs gave me another hard on, which was probably her idea. She asked if there was anything special I'd like to do and I asked her if she could teach me how to eat her pussy. She said she'd never eaten pussy herself but would guide me to make her feel good and maybe come too. I told her that would be perfect. And she mentioned I was losing my shyness with her.

She positioned herself so her butt was on the edge of the couch, her legs spread wide and me on the floor between them on my knees. But I decided this was a good opportunity to examine every square inch of her body starting at her toes.

I picked up her foot and started gently rubbing the bottom and between her toes and the toes themselves. At first she was "what are you doing" which quickly became "wow, that feels so good, don't stop". I decided to see what licking the toes and bottom of the foot did for her and she squirmed a bit and said it made her feel horny. I asked how horny and she just looked at me and pointed to her pussy. Smiling I went back to work on her other foot and enjoyed that she was squirming a bit.

Slowly I kissed my way up her ankles to calves to under her knee which she said tickled. Then moved to those soft and creamy thighs. At first I tickled her and then licked and nibbled, slowly getting closer to her pussy, but ignoring it for now. She said I was making her so hot to please dive in. But I didn't and spent more time on each thigh, slowly getting closer to the treasure.

Finally I got to her pussy. At first I sniffed and found the smell interesting. She didn't have much hair and apologized for that saying it seemed to grow very slowly down there. I had no problem with that.

Tentatively at first I licked along the edge of the thighs to the edge of her pussy lips. I took her lips between my fingers and gently opened them. Massaging gently then licking the outside and then inside, slowly at first. Cary was squirming and make rapid breaths and moaning. I asked if she were OK; smiling and she said please don't stop.

Gently still separating her lips and taking a lick and she let out a small yelp. I looked up at her and she was glued to my face. I took a lick higher barely touching her clit, then higher onto her clit and she lost it. She grabbed my hair and pushed me into her pussy and ground herself onto my face, using her legs pushing me deeper into her pussy while letting out this low moan and then froze. A few moment later she let go and dropped her legs. My face was pretty wet and she was grinning like crazy. I went in for more and licked up more and around more and back to her click, which was enlarged a bit. So I swirled around it and then across it and kept repeating that and before I knew it she was repeating and then yelled please stop before I pass out.

After a brief pause, the took both her feet and pushed me back, jumped off the couch and on top of me. She said that were the two most incredible orgasms that she had ever had. Being much, much stronger than when she played with her self. She said having someone else do it to her was incredible and I would be doing it again to her before she left tomorrow.

In the mean time, she practically ripped my bottoms off and stuck my dick in her mouth. She bobbed up and down quickly and I came very quickly. She then snuggled up to me and laid down with me on the floor and we dozed off. I awoke 2 hours later, slightly chilled. So I woke up Cary and said let's go up to my bed and get warmer and more comfy. Which we did and awoke once again to sun streaming thru the window since the shade was still up.

It was around 9 am and I was just waking up. I reached over and was stroking the nipple I could reach. She said I was making her incredibly horny again to which I said "oh really" and she reached over and said I must be too. She pushed me on my back and hopped on top of me. But this time she slid forward so her knees were beside my head and her pussy was right above me. A different view and I got the picture and started licking and pretty soon was humping my face which was pretty wet.