Jack is a twenty year old guy that has been in a relationship with his high school sweetheart. She had recently broken up with him in a particularly cruel way. They had been dating for 4 years and both had remained virgins until just two days ago. The previous Friday night, they had a nice dinner followed by a long walk through downtown. They walked hand in hand, laughing and talking as the night got late. She confessed to him that she was ready to "become a woman" and suggested they go to his place for the rest of the night. It was the night he had dreamed of, previous dates ending with him coming home alone and satisfying himself as he thought of her lips that had been wrestling with his just a short time before. On this night however things were different. She was back in his apartment, he was finally going to see her body, sure he had occasionally felt her soft breast, or her grinding in his lap as they engaged in one of their heavy make out sessions, but tonight he would get to see her totally naked. It was a wonderful night, but did not last long. After thirty minutes of kissing, with tongues intertwined, she began to massage his cock through his jeans.

She knew he was well put together as she had felt his hardness countles times as she gyrated on his lap while she nibbled on his lips and tasted his tongue, but never had she been as bold to wrap her hand around his hardness. She felt his hands on her breast, causing her nipples to harden into little point, this was as far as she had allowed him to get, but tonight was different. She could feel his lips on her neck as he worked his way towards her breast. She sat up, unhooked and removed her bra to allow him the access that he had never had before. As his lips found her breasts, his hand moved to crotch of her pants as he began to suck and lick her round orbs that he had previously only dreamed of. Her breathing quickened, and she could feel the heat and the moisture building in her pussy. Pussy, such a nasty word, a word ghat she had never used, but it was the only word that came to mind in this situation. They could both smell her arousal as she began to unbuckle his jeans as he fumbled clumsily with the buttons on her slacks. Once free she raised her hips and removed her slacks and panties as he shyly stood up with his back to her to slide his jeans and boxers down his legs. They both kicked their pants from their ankles and removed their socks. As he turned towards her, they both realized that they were finally naked in front of each other for the first time. Jack felt his cock jump as he realized that he was finally going to lose his virginity to the beautiful woman in front of him. Pre-cum was dripping from his cock as he realized that she was giving herself to him as her first as well. He pulled her to him and began to kiss her deeply as his hand explored her breast and his fingers played through the folds of her very moist pussy.

She wrapped her hand around his stiff cock, free from cover for the first time. It was the first live cock that she had ever seen, much less touched. She was amazed that she could barely make a circle around his cock with her fingers, that the length appeared to be seven maybe almost eight inches long. It was intimidating to think that he would soon be sliding it into her virgin hole. As she rubbed and played with his cock, she could feel it twitch in response to her touches. The twitching became more frequent and she soon felt his hands push hers away as he kissed her and explored her folds with his fingers. She felt her own breathing begin to quicken as he found her little nub, her clit. She pulled his hand away from her, smiled and told him she was ready. She layed down on her back and pulled him to her. He lined his cock up with the folds of her pussy. He felt the excitement as her warmth and heat began to surround his almost painfully hard cock. She looked into his eyes as if to ask if he were ready, he could sense her legs wrapping around his body. Suddenly she arched her back quickly and forcefully, driving his cock past her hymen and deep into her pussy. He felt the resistance only momentarily as her legs kept him pulled deep inside. He did not move and was enjoying the warm heat around his cock until he could feel her slowly move below him. He began to slowly move in and out, the feeling was every bit a good as he had dreamed. He could feel her moving faster and more urgently below him as he began to piston in and out of her with more and more force. Their breathing became labored and he could feel the boiling begin in his balls. He tried to hold out as long as possible, but realized that he has reached the point of no return. He pushed deep inside her one final time as he pumped his virgin load of cum deep inside her pussy. He collapsed on top of her, breathing heavily. She brings his hand down to her breast as she rubs her pussy, aching for her own release. She finally moans, toes curl as she cums on her hand. She lays beside him, hand on his chest as they both fall into sleep.

He awakes the next morning thinking of the wonderful night before. He realizes he is alone in his bed wonders and what she is doing. As he looks around the apartment he sees a note on the kitchen table. She was gone, "Jack, last night and the previous four years have been great, but I know there is so much more in this world. I need to experience more, to see more and I need to experience emotions with other people. You have been wonderful, but I need to find what or who I am. Please remember me fondly and keep our memories of last night. I dont know if our paths will cross in the future or not, but if they do not please dont forget that I loved you first."

That was it. She had left. No idea where she had gone. She doesnt answer her phone, her parents had moved out of state sometime last year. I had no way to contact her and no idea where she may have gone.

All day Saturday and Sunday, I did nothing but lay around the apartment. Looking at my phone every five minutes, hoping to have a missed call or hoping that she would come back, but it never happened. Monday morning I had to go back to work. The day was a fog, unable to focus on what I was doing I left early. I wondered aimlessly around the streets downtown, thinking about Friday night walking these streets with her. I finally stopped in a non de bar to drown my sorrows. I sat there for a couple of hours sipping Crown Royale as I watched the place fill with people. I was not interested in meeting anyone so I just kept to myself nursing my drinks. As the placed filled up it became obvious that most of the people here were regulars and were intense fans of the football game that was on Monday nighf football.

As I sat there I sensed a presence next to me. I turned on my stool and saw a beautiful woman had sat down next to me and ordered a drink. I smiled at her and said "Hi". She smiled back and commented that we appeared to be the only people here not watching the game. I told her I wasnt a big fan of football and that it had been a long weekend and that I was washing it away. I turned back to the bar and ordered another drink just as one of the teams scored. The whole place erupted into an extremely loud cheer making it impossible for anyone to hear anyone else. After the cheer died down, the woman next to me smiled and extended her hand. "My name is Pam, your mood doesnt seem to match the atmosphere here. I know a little place around the corner if you want to talk." Now, I have only dated one person since I was fifteen, I am not a ladys man or someone who frequents bars looking to hook up with women, however she is right and she is gorgeous, so I agree.

As we walk down the street I tell her about the events that happened the previous friday/Saturday. She is a very good listener and justs nods or smiles at me occasionally. We get to the door of a small bar and I hold the door to allow her to enter first. Even though I am still focusing on the events of the weekend, I still notice how nice here ass looks as she walks in front of me. We sit at a table off to the side of the bar. There is a pretty good crowd here, but we can comfortably talk. The music is playing rather low and we have a view of a few couples slow dancing on the dance floor. Pam is easy to talk to and lives to smile. We talk about our jobs and our lives and just generally learn about each other. We start to people watch and talk about the different couples on the dance floor. Soon she has me smiling and even laughing occasionally as we guess what is going on with the different people. As the night went on we both worked on a very healthy buzz. We were holding hands on the table and laughing. Suddenly as a faster song ended and a slower song started Pam leaned across the table and kissed me lightly on the lips. She looked into my eyes and said "dance with me". She pulled me onto the dance floor and snuggled up close and we started swaying to the slow music playing. Then she looked up and kissed me again, this time much deeper, probing my lips with her tongue. I let my hands drop to her ass as I feel my cock begin to swell. I am sure she can feel it as she presses up against me.

We go back to the table and order another round of drinks, but this time she moves her chair to my side of the table and rests her hand on my thigh. As we watch the people dancing I can feel her hand working its way towards my crotch. She raises her head for another kiss as her hand grips my cock through my loose fitting pants. After a very intense kiss she nibbles on my ear and whispers that she lives alone just around the corner, suggesting that we move the party there so that we can be more comfortable. I motion for the waitress to bring our check and lean in for another kiss, all thoughts of the previous weekend just a distant memory. Once I paid our check we walked out into the night, hugging each other close as we walked towards her apartment.
Arriving at her apartment we were in our on world as we rode the elevator to the third floor. As soon as we walked in the door she was hungrily sucking on my tongue as she began unbuttoning my shirt and pushing it off my shoulders. As we separated, I pulled her shirt over her head revealing a very sexy bra that did little to conceal a beautiful set of c cup tits. She began to lick my nipples and kiss her way down my stomach until she reached my belt. She removed my belt and unfastened my pants, then standing and leading me into the bedroom. She backed me up to the edge of the bed and began to slide my pants and boxers down my legs. I realized that she would be only the second person to see me naked. My cock was as hard as steel as she kissed the head and dropped to her knees. She pushed me back and I fell onto the bed as she began to stroke my cock and kiss my balls. I was in heaven having never experienced a real blow job before. She started sliding her lips over the head of my cock as her tongue swirled around the head. Up and down she bobbed her head slowly working it deeper and deeper I to her throat. I feel her hands on the back of my thighs as she raises my legs. I feel her breath as she kisses her way down my shaft, to my balls. I shudder as I feel her spread my cheeks and plants a soft kiss on my puckered ass. I am totally unprepared for the erotic feelings that I feel when her tongue push into my asshole. She is licking my ass while stroking my cock bringing me to the edge and stopping. She continued this several times until my cock was almost in pain from the need to cum. She finally smiled up at me and slid a finger into my now wet ass, as she started to slide her lips down my cock. She pumps one and then two fingers in and out of my ass as she takes me deep into her throat. My hands grip her hair as I grit my teeth and warn her that I am about to cum. She just speeds up bobbing up and down until I unleash what is probably the biggest load of cum I have ever experienced. She uses my hands to pull herself to her feet, she then pulls me up to her and begins a very passionate kiss. As her tongue pushes into my mouth, I realize that she has not swallowed. I flinch and try to pull back, but she holds me tight and I share a very cummy kiss with this angel that I have just met. I spin her around and push her to the bed, I am needing and sucking her beautiful tits. I slowly kiss my way down to her belly button and begin to slide her pants and panties down as I tongue the little jewel pierced into her belly button. As I kiss down her body, I realize that there is something different about her. She sits up on her elbows, smiles down at me and tells me that she has a surprise. She reaches behind her and pull a piece of tape loose, suddenly this gorgeous woman is sporting a 6.5" cock that springs up and slaps me in the face. I sit back in shock. I dont know what to do, I have just spent the whole night kissing and dancing with a guy?, Girl? Not only that, but I let her feed me my own cum in a kiss. As she sees the shock on my face, she explains that she was born a boy, but always felt like a girl. She left home when she was sixteen and arranged to have surgery to give her the beautiful breasts. She lives totally as a girl and no one in this town knows any different. She grabs her cock and points it at me and tells me I should try it. I look into her eyes and slowly my hands finds itself wrapped around her cock. I squeeze amazed at how hard and how warm it is. I slowly stroke it and see a drop of pre cum appear on the head. I bend down and kiss the drop and find that it has no real taste. The smile on her face encourages me to try more. I begin ti lick up and down the shaft, massaging her balls. I work on taking more and more of her cock into my mouth. I can't get more than four or five inches into my mouth without gagging. I keep treating her cock the way I enjoy having mine treated. Before long I can feel her breathing change, her hips begin to push up to my mouth. She warns me that she is about to cum, not wanting her to feel like I wasnt as interested in her pleasure as much as I was interested in mine, I keep sucking and using one hand to stroke her cock. I hear her moan and she begins to shoot her load into my mouth. I nurse on her cock u until I feel it getting softer in my mouth. I smile at her and look into her eyes and move to share a passionate kiss. She smiles back as she realizes that I have not swallowed and am now sharing her cum with her. I sit back and smile, thinking to myself that in the past three days, I have lost my virginity to a beautiful woman, felt another woman finger my ass while sucking my cock and swapping two cum kisses with a girl with a beautiful cick. As we lie there thinking she raises up and says that she noticed hard I came with her fingers in my ass. As I smiled back at her, she works a finger to my ass and asked me "guess what I am going to slide in there />
Should I continue?

story by: mickeyfinn

Tags: fiction first time bi-sexual sex story

Author: mickeyfinn

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