The Best of Both Worlds

By Tammy Jones

Published on Mar 16, 2000

Transgender

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The Best Of Both Worlds

By

Tammy Jones

This is a work of erotic fiction. It contains graphic sex. If you are offended by this, don't read it! If you are under 18, get lost! None of these people are real... just little corners of my mind that I sometimes let out to play......

Hi all! My name is Rachel, and I just have to tell you what happened to me last weekend! It was one of the most wonderful experiences of my life!

First, I suppose I had better tell you a little about myself. I'm 25 years old, 5'7" tall, 115 lbs., long black hair, green eyes, 34C breasts, and an athletic build. I work as a secretary for a real estate agency, putting in my 40 hours during the week, then partying with my girlfriends all weekend. I am also a lesbian, having never been with a man (my best friend took my virginity with her mother's vibrator when I was 15) and never really wanting to be mauled by one. Some of my girlfriends, who are straight, kept telling me I didn't know what I was missing, but I didn't believe them. I was soon to have a slight attitude adjustment, however.

You see, I had grown bored with my current lover, (or rather, we had grown bored with each other) and she packed up her things and moved out of my apartment early last week. I moped around for a few days, and then, on Friday, I decided to go out and have some fun. I left work early, around 1:00 PM, and went home to change. As I stripped off my dress, I started getting really horny. I decided to put on something sexy and go out on the town.

I stripped off my bra and panties and put on my really short, black mini-skirt and a tight-fitting white pullover sweater,black fish-net stockings, and completing my ensemble with my black stiletto heels. I got in my car and drove to my favorite watering hole, downtown. As I drove, I got more and more turned on by the feel of my sweater rubbing on my naked breasts, and the breeze blowing up my skirt over my newly-shaved pussy. I was pretty hot by the time I got to the bar, but was disappointed to discover that I was the only one in the place. I debated whether to go somewhere else, or wait where I was. I finally decided to sit down at one of the tables to see if anyone new would show up. Boy, am I glad I did!

I had just sat down and ordered up a gin and tonic when the door opened and in walked a vision of heaven. It was the most beautiful woman I had ever seen! She was dressed in a white, mid-thigh skirt, slit on both sides, with matching blazer, stockings, and high heels, and a royal-blue blouse. Her figure was one to die for; long, sexy legs curving up to her gorgeous hips, at least 36D breasts, long, flowing blonde hair sweeping down over her right shoulder, and the biggest baby-blue eyes I had ever seen. She stood there, framed in the sunlight, looking around, and I thought I would die from the sight of her! Then she walked in, smiling hello to me as she went by my table, and sat down at the bar. I sat there for a moment, drinking in her beauty, and then went to introduce myself.

"Hi, I'm Rachel " I said, sitting down beside her, "May I join you?" She smiled, turning to face me a little, and said "By all means!" I knew right then that I could seduce her if I played my cards right. She introduced herself as Linda, and said she was a salesperson just passing through on her way to a convention in L.A. She had been bumped from her flight and had to wait till 11:00 tomorrow for the next one. I smiled at her, and said " Your misfortune is my gain, that's for sure!" She just smiled at me again and I new I was going to have her.... it was only a matter of time!

We sat there for a while, talking, getting to know one another, and as we talked and laughed together I began to feel close to her. Even though we had only known each other for a little while, I began to feel like we could be great friends.I found that we shared common interests in food, entertainment, and our outlook on life in general. I began to feel very close to her, and I could tell she was feeling very much the same about me. We sat there talking for about an hour and the place began to fill up. It was getting a little crowded at the bar so we decided to adjourn to a private little booth in the corner. We picked up our drinks, and I followed her to the booth, watching with increasing lust as her gorgeous hips swayed back and forth under her dress.

We sat down together in the booth and watched the people dancing. It was a gay bar, of course, and I got more and more turned on watching the ladies making out on the dance floor, the men kissing each other, all moving to the beat of their own drum. On an impulse, I took Linda's hand in my own, and, when she didn't pull away, I could no longer stop myself. I began to kiss her, running my hands all over her beautiful body, trying to drink in her very essence. We got into some very heavy petting, breathing hard, and her hands found their way inside my sweater. Up until now she had remained rather passive, allowing me to be the aggressor, but now she was pinching my nipples hard, sucking my tongue into her mouth and eliciting several low moans from me as my arousal increased. I found myself wanting her more and more, and I moved my hand up her thigh inside her skirt, trying to reach her pleasure center. She stopped me, though, before I could get there, grabbing my hand and pulling away from me. We gazed into each other's eyes, and I knew she could see the hurt in mine. " I don't understand" my eyes said to her. I knew she was aroused.... she was breathing heavily, and I could clearly see the outline of her huge nipples through her blouse. She hesitated, and I was just about to stand and leave when she suddenly squeezed my hand, leaned close to me, and whispered " Why don't we go someplace a little more private?" I smiled shyly, and, still holding her hand, led her out of the bar.

It was around 6:00 when we left the bar and walked the two blocks down the street to her hotel. Once inside the elevator I could no longer keep my hands off her. I'm afraid I mussed her quite severely, ripping her blouse open to get at her luscious breasts, licking and biting her nipples through her bra, and running my tongue down the valley between her lovely mounds,savoring the flavor of her body. Her hands were just as busy, groping under my mini-skirt to find my sodden lips, palming my aching pussy, rubbing me to a fever pitch. All too soon the elevator ride came to an end, and the doors swished open to (luckily) an empty hall. We practically ran to her room, and I continued to grope her lovely breasts from behind as she fumbled for her key. I pressed her up against the door as she inserted the key and rubbed myself against her perfect ass, grinding my hips into her till the door popped open and we fell inside.

I kicked the door closed behind us as I continued to grind my pussy against her ass, groping underneath her for her sweet pussy. Just as I was about to get there, she squirmed out from under me and we stood up together. I reached for her again, but she stopped me, keeping me at arm's length with her hand pressed firmly on my chest, fingers splayed out, her head hanging, her lovely blonde hair obscuring her face. "Wait..." she panted, "wait... before we go any further, you must know.... this is my first time with a ...... woman...... you must understand!" She hesitated, then went on "I want you really bad right now, but I'm not sure how far I'm prepared to go." I said nothing, simply standing there, waiting for her. "I want to make love to you" she whispered, " but you must be prepared to stop when I say so...... or we must end this now." At that point, with a fire in my loins that felt like a volcano ready to erupt, I would have agreed to anything, so I just nodded my head and we slowly came together in a heady embrace that felt like the garden of Eden.

We somehow made it to the bed before collapsing, kissing each other deeply, our tongues battling, our hands carressing, our fever rising. We lay there,writhing against each other, and she took the initiative, pulling my sweater over my head, her mouth falling hungrily on my nipples, sucking them and biting them, switching back and forth between them till I thought I would explode. My breasts and nipples seemed to fascinate her.....she couldn't seem to get her fill of them! Finally, when I thought I would die if she didn't move on, she moved her probing tongue down to my navel, swirling around it while she undid the catch on my skirt.I raised my hips up off the bed to help her pull my skirt down, then lowered them gently as she pulled it off, spreading my legs as wide as I could for her. Her eyes lit up, and she smiled wickedly as she saw for the first time my naked, hairless pussy, dripping with my juices, spread wide open for her (and my!) amusement. She stripped off her blouse and bra, freeing her luscious globes, and crawled back up the bed to attack my pussy with her tongue.

I screamed in pleasure as her lips met my nether lips in a passionate kiss, her tongue probing inside me,searching for and finding my clit, sending my passion soaring higher and higher. I've never been one to stay still in bed, and as she french-kissed my pussy I thrust my hips in the air, humping frantically at her face and mouth till she pulled away and moved forward to lay on me and calm me down. It didn't help, though, because as her threw herself on me her huge, gum-drop sized nipple nestled between my pussy lips and rubbed directly on my hard clit. My breath caught, and I choked on a scream of pleasure as my first orgasm of that wonderful night washed through me. Linda must have realized what was happening, since she grabbed her breast at the base and proceded to fuck me with her nipple, sending wave after wave of orgasm screaming through my body.She finally took her nipple away, allowing me to calm down a bit, but quickly replaced it with her tongue, licking up as much of my cum as she could, all over my sensitive lips, and deep inside me, bringing me back to the threshold of orgasm in no time. Suddenly she thrust her tongue as far in as she could, and grasped my clit between her thumb and fore-finger,squeezing gently, and rubbing back and forth. My senses went over the edge. " UUUUUUUUUNNNNNNNNGGGGGGGGHHHHHHHHHH!!!!!!!!!!!! " I screamed, cumming again and again and again,flooding her face with my juices, writhing on the bed, finally begging her to "Stop!!!.... Stop!!!!....I can't take any more!!! ....OOOOhhh GODDDDDDD!!". But she didn't stop. She kept up her ministrations and I kept on cumming in one long, continuous orgasm until I finally passed out from pleasure.

I woke up alone, around 9:30 that evening, trying to remember where I was and what had happened to me. It didn't take long for it all to come flooding back to me as I realized I was lying naked in a hotel room, my body totally exhausted, my pussy quivering from all the orgasms I had had. I panicked for a moment as I realized I was alone in the bed, but relaxed as I heard the shower running in the next room. I decided I could probably use a shower as well, and went to join my lover in the bathroom. On my way there I realized I had yet to see her naked, and that she hadn't gotten off yet! I resolved to rectify that situation VERY soon! I found her skirt and panties lying on the floor in front of the door, and picked them up. I brought her panties up to my nose to breathe in the animal aroma of her sex, and started to get turned on again in spite of nyself! She smelled wonderful, though quite different than anyone else I'd ever been with. There was a wet spot in front of her panties that I couldn't figure out, though. It wasn't really enough to show the high level of arousal that I knew she had attained earlier. Maybe it was her time of the month and she had been wearing a pad. Shrugging off this minor mystery I opened the bathroom door and went inside.

Steam billowed out as I opened the door. I could clearly see her luscious form through the shower door. She had her back to me, and her hand was moving feverishly in front of her. "So..." I thought, "she didn't want to wait for me. I'll surprise her!" But I was the one to be surprised! I carefully opened the shower door and stepped in behind her. She was so into what she was doing that she didn't even notice my presence until my hands cupped her delicious breasts from behind and my mouth descended on her neck. She jumped and almost knocked us both down as I touched her, but slowly relaxed as my fingers and tongue worked their magic on her nipples and neck. I slowly moved my hands down her belly, kissing and nibbling her neck and ear, when suddenly she tensed and grabbed my hands, holding them tightly to her belly. "No! " she cried softly, " You mustn't...". " Nonsense.." I replied, whispering in her ear, "You don't really want me to stop. I want to please you as you did me!" I felt her resistance melt as I slowly kissed my way down her back to her gorgeous ass, then ran my tongue all over her cheeks and down her crack. But I wanted more, so I grabbed her hips and slowly turned her around.

I sat back on my heels in shock when she turned around. There, just inches away, onder a small tuft of blonde hair, where I expected to find her lovely flower, was an erect penis! I looked quickly up into her eyes. " Surprise, surprise " she said. I didn't know whether to be angry or disappointed. I looked back down at her cock, and as I studied it, my lust began to grow anew. It wasn't very long, only about 5 inches, I suppose, but it was so thick! It looked to be around the size of a soda can! She had shaved all the hair off her balls and groin and there was a clear fluid oozing out of the little hole at the end. I leaned forward to get a closer look, and I caught a whiff of her scent. An animal lust suddenly burned through me, and I buried my face in her genitals. "Oh God, Rachel..." she moaned, as I rubbed my face all over her cock and balls. Wanting to taste her skin, I sucked one of her balls into my mouth, then ran my tongue up a big vein I found on the underside of her cock till I reached the head. I tasted the fluid leaking out of her, and knew I wanted more. I looked up into her face, and her eyes begged me to continue so I stretched my mouth as wide as I could and took her cock into my mouth.

She tasted wonderful!! So different from anything I'd ever had before. I sucked as much of her cock as I could fit into my mouth, then swirled my tongue around the head. She was moaning constantly now, and thrusting her hips at me. She put her hands on the back of my head and held me in place, fucking my face. " Oh God yes, Rachel," she cried, "Just like that... suck me ... suck my cock!" I had never done this before, but she seemed to be enjoying it, to say the least! After a couple of minutes of this, I felt her cock suddenly grow even bigger in my mouth and she let loose a torrent of her cum inside me. There was so much of it that it started to escape my mouth, running out the corners and down my chin before I could swallow it all. She came for about thirty seconds, spurt after spurt filling my mouth before she was finished. I let her slowly softening cock slide out of my mouth and stood up to kiss her. She licked her cum off my chin and buried her tongue in my mouth, grinding her body against me. " Oh Rachel, I needed that so badly! " she whispered, "Thank you so much". " I hope you aren't finished yet" I replied, " 'cause I really want you to fuck me with that thing of yours!" She just smiled, took my hand and helped me out of the shower.

Her cock was hard again by the time we finished drying each other off, though there was no drying my pussy now! My juices were running down my legs in rivers! She cupped my pussy with her palm and rubbed me to a frenzy, inserting two fingers inside me and rubbing my clit. She kissed me deeply, and my passion rose even higher. " No, wait..." I gasped, breaking the kiss, " I want to cum with you inside me!" I could feel her hard cock pressing against me, and I wanted her inside me in the worst way! She smiled and led me into the bedroom, laying me gently on the bed. I spread my legs as wide as I could, closed my eyes and waited.

When I opened them she was between my legs, crawling toward me on her hands and knees. What a sight! My eyes drank her in as she came forward, her face hidden by her long blonde hair, only her flashing blue eyes visible, the gorgeous mounds of flesh hanging from her chest, the nipples hard and ready, and there, just visible between them, her hard, thick cock ready to rip me in half. She crawled up over me and I felt the head of her cock burning against my pussy. Her weight descended on me and I screamed as her cock entered me. I felt so STRETCHED as her cock penetrated my hole, going deeper and deeper. She silenced my screams with a kiss, shoving her tongue down my throat as she slowly began to fuck me. In and out .... In and out , taking her time, building up speed until she was humping me so hard the bed was banging against the wall. I felt so intense...I had never been fucked like this in my life! I was so overwhelmed by her ... the feel of her cock moving inside me, her nipples searing into mine, her tongue welded to my mouth....that I felt like I would explode! She was fucking me really hard now, ripping into me with that thick cock, and my fever burned to a new height. "Oh yes, Linda, fuck me! " I cried, " I'm gonna cum!!! ... fuckmefuckmeFUCKMEUUNNNGGHH!!!" I felt her cum spurt deep inside me and that sent me over the edge. I came so hard I thought I would die. Wave after wave of pleasure coursed through my body. I wrapped my legs around her back and dug my nails into her ass, holding her there inside me till we were both spent, and we fell asleep in that position, her cock still buried in my pussy.

When I awoke later that night she was still inside me, slowly stroking in and out of my pussy. We made love the rest of the night and on into the next day and the next! We fucked and sucked each other in every position we could think of. I fucked her ass with my trusty strap-on and she fucked my ass, nearly ripping me apart. It took us nearly thirty minutes of exsquisite pain and steady pushing before I could open far enough to get her all the way inside, but the pain quickly turned to pleasure as she pounded that thick monster into my ass. I came in a gusher that soaked the sheets! I wanted it to last forever, but I knew it wouldn't. Sure enough, when I woke up Monday morning she was gone, but she had left a note on the bed. She wrote:

My Dearest Rachel,

I want to thank you for a beautiful weekend. I have never had so much pleasure in all my life. I only ask that, when you're in bed with your next lover, caressing her softness, you think of me.Know that I will remember you always!

All my love,

Linda

I crumpled her letter to my breast, relaxing in the afterglow of a beautiful weekend, missing her already. I remember thinking, as I lay there, that it truly had been the best of both worlds!

The End

A Note to the Readers:

For those of you who have read my other stories (Lauren and Jennifer/beginnings and Sisterly Surprise/incest) it may seem I have strayed from the path. I can only say that this was one of those "little corners" I have mentioned that refused to stay inside my head.

Please send all correspondence to tammyjones@lovergirl.com and specify which of my stories you are referring to. Comments are always welcome... I love to hear from you all!

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