A Shy Jewish Teen's Very First Time
By nutmegman - Listen to the ► Podcast at Steamy Stories.
In 1981, I was a good Jewish lad, living in a little town in Western Massachusetts. I was still in high school and had 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 Carrie. She was in my Temple USY (Jewish religious youth group) and a little younger than me at 18.
Carrie helped me overcome my shyness with her when we were very little, so that we remained close friends and spoke almost daily on the phone throughout our teen years.
We would talk after school on most days. She was also dating my best friend. So I'd see her over at his house and at USY activities. Somehow, I was usually squished up next to her in car pools. She'd whisper something in my ear on those moments, and get me smiling, and I'd shush her so her boyfriend, Howie, didn't catch on. She was just 5 foot & a cute girl with dark shoulder length hair, big eyes, really cute face and body; and huge boobs, really. I was actually more interested in her older sister who was a year older than me and was less curvy. Big boobs were okay, But I wasn't obsessed with huge boobs, but Howie was. Howie was entranced by them. He spoke about those huge boobs all the time, more than the personality inside. And Carrie knew that, but she still stayed dating him.
And so it went with Howie telling me he was dying to get to her tits & twat, and how she was going to be his first. Then, with Carrie talking to me at other times, she was telling me what Howie wanted to do to her, and how she wasn't ready, and that he was pressuring her. Then she told me she went on the pill with her mother's permission to be extra safe even though a condom was going to be used if & when Carrie did have sex.
Nothing happened between them, yet. Howie had been pushing for about 2 months and was getting aggravated in his wait. Time was passing.
A bit about Jewish views on fornication: Unlike Christian teaching that all sex outside a marriage is clearly a serious sin, Jews are taught to make a reasonable effort to follow the religious law. Once a Jew believes he's tried to do his best, he doesn't feel shame for 'falling short', spiritually. He met his obligation.
A few weeks after the start of our senior year, I told Carrie that 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 friend's home in Salem for the weekend and they were spending the weekend in Rockport. The house was mine to relax in. I only told Carrie. See, I wasn't a partier, which my parents knew, so they weren't worried about that. They also left me the other car as I had earned my driver's license a few months prior.
Carrie suddenly loved the idea that I was going to be alone and she wanted to join me for the weekend. I said; "No because Howie would kill me". But she concocted a plan with a girlfriend of hers who lived just a few streets away. Howie evidently thought she was having an 'all girl weekend'. He figured he wouldn't see her at synagogue, either.
Sabbath Night
Late Friday afternoon, about 5 minutes after my folks were gone, & before I knew what was going on, Carrie was ringing the doorbell with a backpack of clothes in her hand. I let her in and she grabbed me in a big hug. Okay, this was getting interesting. I was kind of shocked by the hug, but I 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. I had been cutting lawns and doing odd jobs and had money and always paid my own way. Carrie's family was wealthy (by my standards) and she didn't work other than the odd babysitting job, and had a nice allowance each week. While we were waiting for the pizza, I showed her my sister's room and put her bag in it. We made sure she was not visible when the pizza came, as I knew the delivery person. She went up and changed into some flannel 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.
The pizza was consumed and we went and watched TV. 1981 was before cable TV (as we know it today) and we only had over-the-air TV.
We watched whatever was on. I sat in my usual spot on the couch and much to my extreme surprise, Carrie came & sat right next to me. 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 that it was dark in the livingroom so she could not see the stiff tent in my pj's. Or so I hoped at least.
I remember vividly how she told me she was on her knees in front of Howie, just wearing her bra & shorts; and how she was touching and feeling him and how hard he was. How she stuck her tongue out and licked him as "his thing was drooling". She said he tasted salty. I kept saying I really do not want to hear this. But she went on anyways. She really seemed to love talking about sex, & telling salacious lurid details.
She told me how she licked her lips to make them wet and soft. I said they were probably always soft. She shushed me and kind of turned in to me and laid her hands on my thigh, leaning more onto me and was whispering in my ear. I could feel her hot breath near my ear and I 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 breathe and glued to her every word.
So she started her bawdy story 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. She chose 'dick'. And then she 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. Carrie then said she was holding his balls in her other hand and they were getting tighter. She also said she pulled back until just the head was in her mouth and she was tonging the top; and then 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 really big, and she looked at me, her eyes lit up and she grinned. I was looking at her looking at me, not knowing what to say or do.
She resumed her tale of the blowjob, saying 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? She said; "My older sister had told me, and said she'd read it in a magazine". Carrie 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 horny smile on her face.
Carrie said that Howie got down on the floor with her and removed her bra and started feeling up and playing with her tits. I now felt those same luscious tits pushing into my side. She said he was rough with her tits and hurt her a little bit. She said it 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.
I was there, alone with Carrie & listening. I already knew some of it, as Howie gave me the broad details. She knew that I knew, and I'm pretty sure she was enjoying the torture she was doing to me. She then leaned into me a bit more, pushing more against my hard dick and she whispered in my ear that she doesn't want Howie to be her first.
This surprised innocent me. And she then leaned 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 into a 3rd. By the time of the 3rd kiss, 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, speechless; and she laughed.
She scooted up & was quickly sitting in my lap, my boner under her pussie, but she pushed her crotch down a bit. We kissed a few more times and I was getting the hang of it and enjoying it immensely. She knew she was now the first girl I had ever kissed.
I was overwhelmed by Carrie's 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 that 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 I was loving every minute of it.
The late news came on so we decided to call it a night, shutting off the TV and going up to the bedrooms. I was looking forward to jerking off as soon as I got alone, probably a few times before I would be able to get to sleep (wondering if I even could sleep), while sexy Carrie slept in the next bedroom.
But it didn't work out that way. I decided to sleep in my boxers and I crawled into bed. I was thinking about what had just happened, when Carrie softly 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 shifted over to give her more room, then I laid on my side, facing her. I put my arm out and she laid on it and slid in really close. I think she had changed out of her full pajama set & just put on a big t-shirt on and I 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 wide awake. I LOVED the feeling of her body on mine but I was wide awake and knew there was no possible way for me to sleep with her this close. But I didn't care as she felt so nice! I have a sexy girl in my bed with me! To hell with sleep!
After a few minutes Carrie said it was so nice and comfy, she thought we could stay in bed all weekend. I agreed. She then adjusted her body, rolling halfway onto me, leaned up and started kissing me again. I figured that with her beside me, she wouldn't feel my boner. I was wrong. As she slid over, completely on top of me and straddled me, there was no way she didn't feel me and I was wearing loose boxers which did nothing to restrain my predicament.
There was very little light in the room so I couldn't see her. She must have been thinking the same thing, so she reached over and snapped up the shade which let in some moonlight. I said she looked very beautiful as I held her head in my hands. She bent down and kissed me again. Then she got this mischievous look on her face.
Carrie 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 my cock a little squeeze and I think I moaned. Carrie then hooked her thumbs into the waist band and pulled down my boxers, Sitting up she pushed my legs together until the boxers were completely off; and she 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.
Carrie leaned over and licked the tip of my stiff 'flagpole'. I was drooling pre-cum 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. Oh My Gawd, 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? I squeaked out a yes. She asked if she should continue and I think I said; "Gawd 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.
Carrie then lifted her head 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. 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. Carrie produced a towel from somewhere and wiped off her face whatever 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.
Carrie looked at me, eyebrows raised and smiled again. I said; "Sorry, I couldn't help it". She said she was honored and she slid back down the length of me again. I said wait, but she didn't.
This time she engulfed my cock and bobbed up and down much more quickly. 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. No towel needed this time.
Carrie 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 I think I passed out.
Somewhere in the middle of the night, 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 Carrie'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 Carrie.
Gradually I was kneading her butt and thighs and touched her. 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, Carrie 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.
Sabbath Morning.
I awoke with the sun streaming in having no idea what time it was. Carrie was watching me with a smile on her face. I asked what time it was and she said a little after 11 am. We slept through synagogue. 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 that I wanted to shower and Carrie said; "Hey, that's a good idea". I said she could go first and she said; "Uh uh."
"Why not?" 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 to 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 sometime in mid-afternoon; to check on me. When Carrie figured out who I was talking to, she started playing with my dick. No fair as I couldn't acknowledge her and it made talking to my parents difficult (which she found extremely amusing). My parents told me they were staying thru dinner on Sunday and would probably be home around 8pm.
When I hung up, I told Carrie and she smiled the biggest 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.
Around 7:30, Carrie said she was hot and she just took off her bottoms, giving me the treat of admiring her ass & pussie. 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 pussie. She said; "I've never eaten pussie myself, but I could guide you to make me feel good, maybe even set off an orgasm? Would you like to give me an orgasm". I told her that would be perfect. And she mentioned I was losing more of 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 puzzled; "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 pussie. 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 I moved to those soft and creamy thighs. At first I tickled her and then licked and nibbled, slowly getting closer to her pussie, but ignoring it for now. She said; "You're making me so hot! Please dive in." But I didn't. I spent more time on each thigh, slowly getting closer to the treasure.
Finally I got to her pussie. 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 pussie lips. I took her lips between my fingers and gently opened them. Massaging gently then licking the outside and then inside, slowly at first. Carrie was squirming and made rapid breaths and moaning. I asked if she was okay. Smiling, she said; "Please don't stop".
Gently I was still separating her lips and taking a lick. 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 just absolutely lost it. She grabbed my hair and pushed me into her pussie. Carrie ground her sex onto my face, using her legs pushing me deeper into her pussie while letting out this low moan and then she froze, stiff. 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. I licked up and around her mound, and back to her clit, 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 convulsing and then yelled; "Please stop before I pass out".
After a brief pause, she took both her feet and pushed me back, jumped off the couch and on top of me. She said those were the two most incredible orgasms that she had ever had. Being much, much stronger than when she played with herself. I enjoyed my first success in pleasing a woman! And I did it twice in one setting! I'm a sexual beast!
She said having someone else do it to her was incredible, and she informed me that I would be doing it again to her before she left tomorrow.
In the meantime, 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 Carrie and said let's go up to my bed and get warmer and more comfy. Which we did and when we next awoke 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 straddling outside my shoulders and her pussie was right above my nose. I got a lovely view and I got the picture. I started licking and pretty soon she was humping my face which was getting pretty wet.
She started sliding her knees down me and stopped to give me a kiss and I asked about her tasting herself and she thought she tasted okay. She slid further down and then knelt straight upward, and positioned herself right above my dick. I said she didn't have to do this. She looked at me incredulously and dropped her wet cunt onto my dick, and leaned down to give me a slobbery wet tongue action kiss. Then she started bobbing her ass up and down and soon we were both close. I said she felt incredible. She stopped and asked me for more details about how it felt for me; to which I replied "smooth, very warm, and oh so wet" (which made her blush) "and of course incredibly good". She started going up and down more rapidly and I pushed in rhythm. Soon we both let out slow moans and I came again and she said she did too. She collapsed down onto me, pulled the covers up and we dozed off again.
A short while after we got up and showered, she declared we would stay nude the rest of the day. We ate some bagels for brunch and went back to the couch. I decided I wanted to taste her again and started licking and she told me what felt good and what felt really good and what tickled and what teased her. Soon she was wet again and I was plunging fingers into her pussie nice and quick. I bent down and licked her clit again a few times. She froze and let out a moan. She said I ate pussie real good!
She grabbed me by the dick and went into the kitchen where she bent over the table and she told me to fuck her real hard from behind. It was the first time she used the word, 'fuck'. She said she couldn't believe how horny she was and wanted it fast and hard. I obliged. Twice.
Hot, sweaty, & hungry again; I made us some quick peanutbutter & jelly sandwiches. I didn't want this magical weekend to end and neither did she. We talked about how incredible everything was and how we would get together again somehow, soon. We did some snuggling back on my bed and then she somehow got me hard again and slid on top of me for a long, slow fuck and fell on top of me.
I saw it was a little past 5 pm. We pulled off the sheets and started a wash. Took another shower together and put the towels into another laundry load. Remade the bed, cleaned up the house a bit, & we had about 90 minutes before she had to leave.
We snuggled, touched, kissed some more. I asked if I could eat her pussie one last time to which she said; " No, I'm raw and need recovery time".
I apologized for hurting her and she made sure I knew it was the best kind of hurt she had ever felt. She looked over and saw some Vaseline on my night stand and her eyes sparkled. She reached over and took out a goop of it and started stroking my growing dick. Somehow I got it up and came again and she wiped it up, cleaned me up and we got dressed. We kissed and hugged and kissed some more and said we would find another way to get together, that this was incredible. But we both promised to not say anything to anyone.
She ended up eventually having bad sex with Howie and then they broke up. Then she told me, still in our daily phone chats, that her dad got transferred and they were moving to Phoenix in 2 months. And that we needed to get together somehow before then. I agreed.
Carrie moved 9 weeks later. We kept in touch for years via mail letters, but gradually lost contact with one another. Even though I have been married many years now, I still think of that one, amazing weekend and the special girl that got away. I often wonder what happened to her as I have been unable to find any trail on the internet.
I never told anyone until now. The secret stayed.
By nutmegman for Literotica
from Steamy Stories Podcast.
