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Getting the chance to see the woman I lost my virginity to.


written by:
Patrick O’Connor

It was July of 1988 and I was on vacation with my family in North Carolina. I was a skinny 14 year old who looked older and not to toot my own horn but I was a pretty good looking guy.

I had been hanging out with a group of kids who were between 16-19 specifically I had been close to two 18 year old guys who were literally the best looking guys I'd ever seen. I told them I was 17 as well and I had to prove myself during a couple of games of touch football because they were both the stars of their teams. Luckily I made up for my skinniness by using my speed to score a few touchdowns during the games. During the last game the there was a beautiful girl watching us and I was pretty sure she was checking me out but at the end of the game one of the other guys made a beeline to her and I was left feeling like I wasn't good enough.

She hung out with us for a little while and when she left I asked him if he was interested and he replied with "Well I'm interested in her getting on her knees and sucking me off." He was supposed to see her later that night but he found a girl more to his liking and blew her off.

After dinner I went for a walk on the beach and found her sitting on the sand crying. She saw me and I could see how upset she was. The moon was illuminating her face and up to that moment I'd never seen a more beautiful girl. She looked at me and said,"hey weren't you playing football earlier with those two guys?" I answered yes and decided to tell her the truth about what had happened. So I sat down next to her and told her she was way too good for that guy and that he was off with another girl.

Now up to this point in my life my sexual experience was limited to making out with a couple of girls and feeling the tits of the girl who was my girlfriend earlier that year. As I sat next to her I decided to go for it and told her how I had noticed her during the game and that I had a hard time concentrating because of how beautiful she was. Hearing this she rested her head on my shoulder and asked me how old I was. I told her I was 18 to which she replied she was also 18.

She told me that we should go for a walk and as I stood up there was little I could do to hide the ginormous erection I had. She quickly looked down at it and smiled,"are your parents in?" I was supposed to be back at our condo at 9:30 because my parents were going over to another couples place to hang out and have some drinks and I had to watch my little sister.

I told her this and she asked if I needed help babysitting with another smile on her face. She then asked what unit we were in and said she was going back to her unit so she could freshen up. As we walked back to our resort I had a million thoughts going through my head and when we got to the pool area she looked at me and told me how much I had made her feel better and then she said that she would see me in a little while.

I walked towards our condo and was trying to figure out how to hide the massive erection I had now had for about 30 minutes. Finally after walking around for the next ten minutes I walked into my condo and chatted with my parents for a little bit hearing that they would probably be home after midnight.

I went to take a shower and heard them say goodbye and then got out and as I was drying off I heard the door open and then heard her voice. I yelled "I'll be out in a minute." I quickly dried off and came out, she was sitting next to my little sister and she looked fucking amazing. My sister was 8 years old and luckily she was falling asleep fast, I took her into her room and read her a story about as fast as I could and within a few minutes she was fast asleep.

Now as I came back into the living room I was a perfect combination of nervous and excited, not because I knew I was about to get laid but because I had this absolutely stunning girl waiting for me. She was sitting on the couch with her feet on the coffee table and looking at me with a look I would later recognize as a look of lust in her eyes.

I sat down next to her and she told me that we should go to my room, I told her that my room was the same room was the same as my sister so she took my hand and led us to my parent's room and once we got there she looked at me and told me that she was very impressed with my performance in the game earlier. I just stood there not knowing what to do knowing that I had another throbbing erection bulging from my shorts.

I was looking at the most beautiful thing I'd ever seen, she was about 5'10 with the kind of body I'd only seen in much older girls. She had a pair of shorts on that were covering her bathing suit and her shoulder length hair was still a little wet. I was so fucking nervous and it almost felt like she recognized it because she came up to me and looked me in the eyes and told me that she thought I was cuter than the other guy who in my eyes was a man while I was in my mind still a boy.

But her words gave me the confidence to pull her close and kiss her. When my lips met hers it set off a spark that made her grab my ass and pull me closer to her. We were making out with a kind of passion I had never felt before. I felt her hand on my hip as she ran her mouth from mine to my ear. Then she pulled away and got onto the bed and I followed her with my throbbing cock leading the way.

Now if you remember up to this point I had only felt the tits of another 14 year old so when she looked at me while lowering the strap on her bathing suit I was completely in awe because I was looking at the most beautiful thing ever. She had a pair of tits that were perfect and I didn't know what to do when I saw them. She took my hand and pulled me onto the bed with her, I kissed her some more until she pulled back and gave me the same smile as before while looking at my shorts Then I was being laid down on the bed and next thing I knew she was slowly pulling my shorts down and when my cock was finally free I had this sexy girl slowly kissing my stomach and moving lower than until I felt warm lips wrapping around my cock for the first time.

She slowly began bobbing up and down, her eyes looking up at me with me being completely lost in the fact that I was getting my first blow job. She stopped and stroked my cock and told me that I was very big. Now I was literally the happiest person alive and I felt like I should be tending to her so I moved to her side and took one of her nipples in my mouth. She had nipples that had sprung to attention and when I sucked on it she moaned softly and then she pretty much took control and laid down. She swung her legs so that I was between them and I was now moments away from seeing my first pussy. I unbuttoned her shorts and she lifted her ass as I pulled them off. She was still wearing her bikini bottoms and again she lifted her ass telling me to keep going. Her bikini was black and as I slid it down her legs all I could think was "HOLY SHIT I'M ABOUT TO SEE IT!!!"

When I finally got it off she looked at me as she slowly spread her legs and said "now it's your turn." I had no idea what to do, I knew I was supposed to lick her but I was still dealing with the fact that I was looking at a real life pussy. I lowered my head between her legs and felt her hands on my head,this is where my love of the smell and taste of a woman was born. She was dripping wet and I began licking her opening and she started moaning. Then she completely took control and her hands guided me a little north where I found a very swollen clit and this is where me paying attention in health class paid off.

The moment my tongue touched her clit she bucked up and her moans turned into a very audible scream. She had her hands on both sides of my head and was controlling me. Her taste was sweet and I felt the pleasure I was giving her as she bucked up and down. I was solely focused on her clit until I decided that I would now also feel what it was like to have my finger inside this beautiful dripping wet pussy in front of me.

As I continued my focus on her clit I slowly put my finger inside her and slid it all the way in. I can still clearly remember how drenched it was and how almost instantly she yelled for me to go faster. She had her hands on my head as she was bucking up and down, her pussy meeting each thrust until I felt her pussy tighten up. My other hand was on her stomach and it was rock hard as she launched off the bed screaming "I'M CUMMING!!!"

She flooded my mouth with her nectar and I remember telling her how much I liked her taste. She then looked at me me and told me that she needed me inside her. When I felt myself slide inside her my whole world went blank. I was lost in the amazing feeling of my cock inside this unbelievable tight vessel of lust. Now I'd be lying if I told you I lasted long and it was almost like she knew it was my first time because within a couple minutes she told me that she wanted me to cum on her stomach but she was too late because I was lost in the feeling. I was pumping as fast as I could and I was already erupting inside her. Now that was 32 years ago, she was the first of many women I've been with and fast forward to the present day where I'm divorced and not looking for any type of relationship. I'm a fella who was married for 16 years to the world's most selfish and unadventurous woman and in the five years I've been divorced I've kinda been focused on playing the field.

One night I got into a conversation with a woman who had the same complexion as her and I asked her what her ethnicity was. She told me she was Egyptian and I was instantly taken back to 1988 because the sexy goddess who was my first was also Egyptian. After a few more drinks I decided to tell my story to this woman in a bar to which she was very entertained. She asked me if I had ever seen her again and I had only heard from her in the form of letters she wrote me. Our sexual adventures happened in North Carolina but she lived in Texas and I was in Pennsylvania. She wrote me in the fall telling me that she was going to college at a school less than an hour from me. I never answered her because I didn't want her to know that I was actually going into the ninth grade while she was a freshman in college.

So when I got home I typed her name and scrolled down and stopped suddenly because I was looking at a picture I recognized. I looked at her profile and sent her a friend request. The next morning I awoke to a notification that she had accepted and I was nervous as what to do next but it didn't matter because within a couple minutes I saw a Facebook message from her.

It said "Is this the same person I met on the beach?" I replied back that it was and she messaged back with her phone number saying that I should call her. Here I was, a 46 year old man who was now lying in bed with the same massive erection I had then. I went through her profile to see that she was a doctor just as she told me she was going to be. She lived in Arizona and most importantly she was in her words "happily divorced" she never had kids and then I noticed her birthdate. She was two years older than me which meant she wasn't 18 back then. She thought I was 18 so I guess she lied to me about her age but that meant she was in college at 16 and then I thought about how she was so ahead of her time sexually.

I called her that evening and we talked for over two hours talking about our lives and careers with me telling her about my kids and then we talked about our relationships. We didn't talk about our sexual encounters until near the end of our conversation and when we did it was her telling me that she had thought about me often over the years because of how much I made her feel safe that night on the beach. She said that she felt a very strong connection with me and that she was hoping to explore it more when she went to college. I listened to her and wanted to tell her that I was only 14 and that she was my first and how I was too embarrassed because clearly she was experienced sexually and I had no clue what to do. Before I could she excitedly told me how she was going to be in Baltimore for a conference in a month. Hearing this I decided that I would tell her everything in person. She was very adamant about getting together and over the next few weeks we spoke more and ironed out a plan to meet for dinner at the restaurant in her hotel.

The day of our dinner I woke up feeling more energized than normal because I knew I was going to be with my first that night. I had looked at all of her pictures and I couldn't believe how good she looked. She looked almost the same as she did back then. I found a picture of me from that same summer and sent it to her. I wrote,"here's a reminder of the guy you met on the beach 32 years ago." She replied back with,"I've always remembered what you looked like, that sexy boy has grown into an even sexier man❤️" I was in my office over lunch and I was looking at her pics and I replied back saying "The sexy beautiful girl I met on the beach 32 years ago looks exactly the same now as she did then, I feel like I'm going to dinner with an 18 year old." I added the last part to see how she would respond wondering if she would say anything. She replied with, "Well that's a funny story I'll tell you about later ❤️"

My afternoon was pretty booked and as I met with my clients I was completely distracted by my thoughts of my evening. It's an hour and a half drive to Baltimore and as I drove down I95 all I could think of was how I didn't listen to anything my clients said because my head was full of anticipation of the beautiful woman I was going to meet for dinner. My mind wandered through how she had picked the restaurant even though I had suggested a couple other places. It was clear she and I had shared the same thoughts since we reconnected and I made sure to get there a little early to see if we could have a private table.

I wanted the two of us to be away from people, dinner was going to be foreplay. So I spoke with the manager and was very straightforward with him about how I was meeting a woman I hadn't seen in over 30 years. He smiled with a look telling me he was in complete understanding. I was led to a table tucked away in a corner, he told me that he would make sure we had total privacy. He was easily one of the coolest guys I'd ever met so I invited him to have a drink with me and to my surprise he accepted. Even better he ordered a Makers's Mark Old Fashioned which I laughed at because that's my drink. He took a sip and said, " Alright tell me about this woman." I smiled and took a sip myself and told him "Well this isn't just any woman, she's the woman who gave me the greatest gift. He looked a little puzzled and I told him that I wanted this table because dinner was going to be my foreplay. I was very blunt in telling him how when he saw the two of us walk out later we were going to get room. He smiled and I told him how I was going to fuck the same woman who was my first. I told him how we reconnected and how she had picked the place. She texted me saying she was in the elevator and with that my new friend got up. I stood up to shake his hand but instead he gave me a big hug telling me that he never drank with a customer before but he was glad he had a drink with me. I put a $50 in his hand and he said "I promise the two of you won't be disturbed."

A few minutes later I watched as the most beautiful woman walked into the lobby. She was wearing a black dress that was tight but not too tight. From afar she looked like the same woman from years ago, the manager led her to our table and with each step I felt the same feeling that I felt as a 14 year old boy sitting next to her on the beach. Here I was a 46 year old man who had to make sure my suit jacket was going to hide the bulge in my pants. I stood up and we embraced, her perfume smelled of cocoa and jasmine, she pulled me so close that I had no way to avoid her from the anticipation in my pants. She kissed me on the cheek and softly whispered in my ear that she was so happy to see me.

We sat down and she ordered a bourbon on the rocks to which I smiled telling her I love a woman who drinks what I drink. She commented on how private it was and how it made her feel cozy. For the next ten minutes we talked about our days, her telling me how she was here to give seminars to students at Johns Hopkins and how she had a very hard time concentrating and me telling her the same thing about my day. We ordered dinner and another round of drinks and I took her hand and told her how she literally looked the same as she did when she was 18. She smiled and said "well that's the funny story I wanted to tell you,when you said you were 18 I lied about my age. She told me how she was worried that I wouldn't have been interested in her if I knew she was really only 16.

I laughed and put my hand on her face and said "well now I have a confession of my own, I told her I too had lied because I had the same worry about her not being interested in me. I told her that I was only 14 and that she gave me the greatest gift of my life. She smiled and described when she was watching the football game and described in perfect details how I was faster than the other guys. She told me she wanted to talk to me but since I didn't make a move she thought I wasn't interested.

"Well it's a very good thing that I went to the beach that night, because that's the night I'll never forget." I moved closer to her and she looked at me waiting for my next words. "You gave me the gift of being the most stunning woman I'd ever seen. You gave me the gift of your perfect body and your ability to unleash my inner passion and lust." She put her hand on my thigh and her lip quivered as she moved her hand closer to the bulge that was absolutely throbbing. I looked at her and told her that she was doing the same thing right now that she did all those years ago. She inched her way closer and I told her that I needed to repay her gift. She let out a very soft moan as her hand was now less than an inch from my cock. I told her that my entire day had been filled with anticipation of the moment I was alone with her and how I was going to make sure her night was filled with the same passion and lust she gave me 32 years ago. And with that I watched as her lip was quivering faster and felt her hand on my cock. She had a look that was almost like a caged animal, she was slowly starting to jerk me off when all of a sudden our food came. She looked at the waiter, smiled while never taking her hand off me and told him that we needed our food sent to room 2211.

I looked at her and she pulled me up from the table and the two of us walked swiftly through the restaurant. As we passed the bar the manager smiled at me and I gave him a smile back. I had to walk with my hand in my pocket to hide the bulge in my pants and when we got to the elevator it seemed like it took forever to come. When it opened there was a group of people that were going to the same floor as us. I stood against the back wall and pulled her into me, she gently pushed back into me for the entire ride and when we got out it was two people running down the hallway. She unlocked the door and I picked her up taking her to her bed. I kissed her and she returned my kiss with an unbridled lust, she was so unbelievably beautiful and she needed to hear my words about how I was going make her feel like the most wanted woman in the world.

I kissed her neck as I gently began rubbing my bulge against her. Her legs opened up as I whispered in her ear that I described the moment I first tasted her and how it was why I was a man who now had an addiction to the taste of a woman. She moaned loudly as I described the feeling when I was looking in her eyes the moment I felt the feeling of my cock sliding inside of her dripping tight pussy. She moaned louder when I told her how she was my first and how I wanted to respond to her letters and how I wanted to visit her in college. She was now pulling me into her moaning louder and louder, I moved over and asked her to stand up and when she did I told her I was looking at the most beautiful woman in the world. She was on fire with lust as I turned her around and kissed the back of her neck and slowly began lifting her dress up. I told her I had been dreaming about this moment since I saw her picture on Facebook and I lifted her dress over her head and was met with a silk black bra with a matching silk silk thong. I unhooked her bra and gently grazed my hands along the same perfect tits with the same swollen nipples that I had years ago. I placed my hand at the top of her thong as my fingers gently pinched her nipples. She was grinding her ass on me as I described to her how I had thought about the moment when I was able to feel the river of anticipation flowing between her legs. She was moaning louder and louder as I turned her around and lifted her up again to carry her to the bed. I laid her down and she sat right back up and had her head face to face with my pants. She unbuttoned my pants and pulled my zipper down and looked up at me and said "I've been thinking about the moment when I get to have the most beautiful cock I've ever seen in my hands. She pulled my pants off and she slowly stroked my rock hard cock in both hands. She looked up at me and said that she couldn't believe that a 14 year old boy had a cock that was so thick. I know that I have a very big cock but I wasn't aware of it back then. I pulled away and she looked at me as I took my shirt off and told her that she needed to give me what I wanted first and she laid back down and opened her legs as I lowered my head between them. I kissed her inner thighs and worked my way up to her thong which was absolutely drenched. She was moaning louder and louder and she lifted her ass up as I slid her thong off.

I inhaled her sweet aroma for a moment as I gently rubbed my finger along her tight dripping slit. She had the most beautiful pussy I'd ever seen, she had the same perfectly trimmed landing strip, her clit was swollen and her slit was glistening as it quivered aching to be touched. I slid my tongue inside her and tasted her sweet nectar and then told her how much I had been waiting for that taste. She moaned and arched her back as I grazed my tongue on her waiting clit, I slid a finger inside her as my tongue went to work on her clit. I took my time and teased her as she was now moaning loud enough for the next room to hear. I asked her if she wanted to cum and she responded by grabbing my head as she had done years before and I focused on her clit as I took another finger and slid it inside her finding her g-spot. She violently bucked up and down with unbridled lust and lost all control of her body as she screamed "FUCK YEEESSSS I'M CUMMING!!!" She launched herself up and I grabbed her ass so I could get every single drop that her pussy was flooding my mouth with.

She collapsed back on the bed but I didn't give her any time to recover before I repositioned myself underneath her pussy. I told her that I needed more of her juices and she lowered herself onto my face and began slowly grinding her pussy on my eager mouth. I felt her hand as she began stroking my throbbing cock. When I felt her lips wrap around the head of my cock I was taken back to the first time I felt that feeling. I couldn't believe the same girl that was the first one to have my cock in her mouth was now cupping my balls and slowly taking every inch of my 8.5 inch long and 6.5 inches of girth in her eager hungry mouth. She moaned as I worked her pussy but then began sucking faster and faster until I slid a finger inside her pussy and then another in her tight ass. She had my entire cock in her mouth when I felt both her pussy and ass tighten up and then she stopped and unleashed a scream that the whole hotel probably heard yelling "FUUUCCCKKK YEEESSS I'M CUMMING!!!" And I was greeted with her pussy flooding my mouth again with a stream of her nectar that can only be described as heaven.

At this point she collapsed on the bed and was almost comatose for a few minutes until I got on top of her and kissed her with my lips soaked with her taste. She looked up at me and told me that she had never felt like this before and then I slowly began rubbing my cock along her slit. I told her in detail how I felt as a 14 year old boy looking down at the same pussy as I was about to fuck. I described the immense rush when I felt her pussy accept my virgin cock. She was looking at me with a hunger as I described how the last time I was a boy who hadn't given her what she deserved and now I was going to make that up to her. I told her that tonight my only focus was her pleasure and I slid inside of her slowly as she grabbed my ass. I paused for a moment to kiss her with the same passion and lust that she unleashed in me 32 years ago. Then I leaned back and wrapped her legs around me and told her that I was going to fuck her unlike any man had ever fucked her before. I was very still with my entire cock inside her and she looked up at me and said "I'm yours, I want you to do whatever you want to me." And that unleashed my lust as I began slamming into her as fast as I could. For the next ten minutes we were both lost as the room was filled with the sounds of my cock pounding her and her screaming to never stop. All these years later and she was just as tight as she was the first time. I looked down at my cock sliding in and out of her and I knew she was feeling things she had never felt before. She had already cum twice but I knew that she was about to feel something she had never felt before and when I felt her tighten around me she looked up at me silently with her mouth wide open and she launched herself up as her body went into a total spasm with her first vaginal orgasm. I slowed down and let her enjoy what was happening until I watched her eyes literally roll back.

She was laying there with her pussy quivering unlike anything I'd ever seen before. I thought maybe she was going to want a little break but I was wrong because she rolled over and took me in her mouth again. She was bobbing up and down and it was because she was hungry for me and I told her as I grabbed her head and began fucking her mouth that she made me not only want but need to pleasure her all night. She pushed me down on my back and slowly lowered herself onto my cock. I told her to find her spot and use my cock to her pleasure. She was going very slow until she screamed "Oh my god here it cums and then rocked back and forth until she came again. It was amazing to look up at a woman who was experiencing the pleasure her body deserved for the first time. She looked at me and smiled then told me she wanted me to cum, I told her I wasn't ready to cum and she got off me and got on her hands and knees and begged me to fuck her from behind. I slid inside her and she pushed herself into me faster and faster until we had a ferocious pace going for over half an hour. As she screamed louder and louder I slid a finger inside her tight ass which almost immediately made her cum again. She then rolled over and looked at me and told me to lie back. She told me that I needed to cum and that she wanted that cum in her mouth. She sucked my cock slowly at first and then picked up the pace until I felt my seed brewing in my balls. I grabbed her head and asked her if she wanted my cum she moaned yes and went faster and faster until my cock erupted stream after stream of my hot thick white seed. She gobbled up as much as she could until she stopped and lay next to me. She had my cock in her hand and was slowly stroking it with more cum still dripping out. She looked at me and told me that she never had cum more than once before. I told her that I had never felt the need to make a woman cum as much as I wanted to make her cum. As she was lying next to me she looked so unbelievably beautiful as she was still slowly stroking my cock. I rolled on my side and her hand went with me as I kissed her. I gently rubbed her back and she let out the softest moan as I gently grazed my hand along the small of her back. As my hand went from the small of her back to gently caress her ass she moaned again. She looked at me as I was caressing her and I felt her hand begin to go a little faster. I gently kissed her neck and ear telling her how beautiful she was, then I took my hand and very gently grazed her inner thigh which was soaked with her juices and she moaned "Oh my god!" Then her hand began sliding up and down using my cum as lubricant because she felt my finger even so gently slide from her inner thigh until she felt it glide along her still dripping wet slit to her clit. She looked at me as I began rubbing her clit with my thumb and sliding two fingers inside her and her legs began to shake. She was now stroking my cock faster and moaning louder because she knew that I was about to make her cum yet again with my hand. She looked at me as she released her nectar again with her mouth wide open and I gently rolled her over onto her back and kissed her. I looked into her eyes and watched as she felt the head of my thick cock along her slit. She looked up at me and we just locked eyes for a moment and I kissed her again. Then I looked at her and she grabbed my ass and pulled me deep inside her as we began a very loud and very wet round two.

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The author of this story: Patrick O’Connor

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