Me and Molly

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Me and MollyThis is a work of fiction featuring Male on Shemale sex… enjoy! I considered myself straight all my life. I say that because I recently had some experiences that changed my inner definition of myself.I met a girl at a local coffee shop. Actually, I saw her there every morning when I stopped in for my morning cup. I’d always admired her figure and beauty from afar, she was a very pretty redhead with a killer body and great taste in clothes. She was always wearing some kind of form-fitting dress that usually ended mid thigh or higher and more often than not a pair of sexy high heel shoes. She was way out of my league, or so I thought until one day she came in right after I’d gotten in line and she said “Hi, I see you’ve beaten me here this morning.” Her voice was a little husky, but very sexy and I said, “Yeah, you’re usually all the way up front by the time I get here.” She held out her hand which was very long fingered with green nail polish that went perfectly with her coppery hair and green eyes, and said, “I’m Molly” I took her hand in mine and gave it a little shake as I introduced myself, “I’m Kevin, nice to officially meet you.”I was having a hard time thinking as she was just so beautiful up close like this and I couldn’t think of anything else to say. I think I was staring at her fire engine red lips and daydreaming when I heard her say, “Are you going to keep my hand or can I have it back?” I could feel my cheeks flush with embarrassment as I quickly let go but she just giggled sweetly and said, “Oh I’m sorry, I didn’t mean to make you blush! That’s so cute!” Well to try to make up for the faux pas I insisted she cut in front of me in line. This allowed me to hide some of my embarrassment but also let me check out her gorgeous figure. Her butt was absolutely perfect and protruded nicely from the green dress she had on. God but this was an amazing woman! She got her coffee and say said, “Well, nice meeting you, maybe we can chat more next time,” and swept past me leaving me swooning in a cloud of her scent.As the days went on she’d arrive at the same time as I did more and more and we got to know each other bit by bit. She worked in a dress shop just down the block and I told her I was an IT guy at a local business. She was single and not currently seeing anyone and when I said neither was I it was actually her idea that maybe we should take our friendship to the next level and go out for dinner some night. I said I’d really like that and so plans were made to meet that Friday night at a local restaurant at 7 p.m. Friday came and I found Molly waiting out front when I arrived at 6:50. She said hi and said that she’d just got there and was only waiting for a few minutes. She looked absolutely amazing in a simple pair of jeans that clung to her like they were painted on and a black camisole top with green piping. Her hair was tied back in a pony tail and showed off her perfect jaw line and sculpted cheekbones. She was wearing a simple pair of emerald studs in her ears and a lighter shade of red lipstick. During dinner the conversation went back and forth with more and more personal information as we really got to know each other better. She said she liked to keep some things private for the time being until we’d been out a few more times. I took this as a good sign because I definitely wanted to see more of Molly. After dinner we went for a stroll and she said she lived nearby and asked if I would mind walking her to her apartment complex entrance. We arrived there much too soon for my taste, I really wanted the night to last forever, but as far as I could tell things were going well and we’d walked the last couple of blocks holding hands which is an intimacy I really enjoy. When we said good night at the front door I leaned in for a kiss and she gave me a peck on the cheek and said she’d really enjoyed herself, that I seemed really nice and looked forward to next time.That last part took some of the sting out of her cheek peck, but I figured she just wanted to take things slowly and make sure it was something serious. After our second date, which also ended at her building entrance, I was rewarded with a peck on the lips. On our 3rd date Molly asked if I’d like to come up and have some coffee and keep the conversation going. Of course I said yes and was soon inside of her apartment. She told me to make myself comfortable while she put on a pot of coffee. I took a seat on a love chair in her living room area (the apartment was basically a living room, kitchenette, single bathroom and a bedroom) and ataşehir escort she put on the coffee and excused herself. When she returned she had traded her dress for a loose sweatshirt, jeans and a pair of slippers. She’d also let her beautiful red hair down and it was cascading over her shoulders. This was one very sexy woman! We talked more and Molly served the coffee. Soon the conversation waned. We were sitting close enough together that our knees were touching and occasionally she’d touch my knee or arm as she talked. At a particularly quiet moment I leaned in for a kiss and our lips touched. Her lips were just so soft, softer than any lips I could remember kissing. I tentatively opened my lips a little and touched hers with my tongue. When I did that Molly pulled back a little and I could see her eyes tearing up. “Molly, I’m so sorry, I didn’t mean to be so forward…” “No Kevin, it’s not you, there’s something I have to tell you before we go any further. I really like you and can tell you really like me, but there’s something about me you need to know.” She proceeded to tell me that she was a male to female transsexual. That she’d grown up as a man, but had always felt like a woman inside. She’d always be slight in her build and had feminine features that made her a target for ridicule and bullying. Fortunately her parents were progressive and understanding and had removed her from school to be home schooled and had arranged for her to see a ther****t to help her learn more about what she really desired. Eventually she had started on a course of female hormones, changed her name from Michael to Molly and began to live her life as a woman 24/7. She said she was still in possession of her male genitalia and didn’t want to have sexual reassignment surgery because of the possible dangers of the procedure and also because it was way too expensive and not covered by her health insurance.She’d tried dating a couple of guys before, but they all turned out to be assholes who were just interested in sex and immediately ended things as soon as they found out about her true self. I was the first guy she’d taken more time with and felt a real connection with and so she wanted to be up front with me before anything happened between us that either of us would regret. She could feel herself falling for me and didn’t want to go any deeper and end up being heartbroken so better to get everything out in the open now before we went any further.When she finished I was dumbstruck. I was having trouble with the dissonance caused by the beautiful woman sitting across from me that I was falling in love with and the reality of her being a genetic male. I had nothing against gays or trans people, I was as liberal as they come, but I’d never considered myself anything but straight and the thought of gay sex repulsed me. But when I thought of gay sex it was the traditional man-on-man that I pictured. I’d never given any thought to a beautiful woman who just happened to also have a penis. The beautiful woman in front of me had me aroused and I felt like none of the other stuff mattered.I told Molly that I too was falling for her, but that I didn’t know how to deal with this situation. As far as I was concerned I was straight, she was a woman and I was attracted to her. I wasn’t sure how to proceed. Molly looked me in the eye (I noticed that sometime during the conversation I’d taken her hands and was holding them in mine between us) and said, “Kevin, one of the big mistakes I’ve made with t
he other guys was to pleasure them with a blow job or hand job. While they were excited and aroused they all professed their undying love for me and said they didn’t care that I had a penis. But as soon as they achieved orgasm they wanted nothing to do with me and ran out of here as fast as they could. At least you haven’t left yet and are open to talking about this.” “I am,” I told her, “I really am attracted to you, and not just your looks, although that’s what I first noticed about you, I think you are a beautiful person that’s very caring and intelligent, I’m just not sure how I’m going to be if we try to be intimate with each other. It’s very important for me to please you too, and I just don’t know if I’m going to be able to cross that hurdle.” Molly leaned in close to me and asked, “are you willing to try an experiment?” “What kind of experiment?” I asked. “Let’s continue this date as it would have progressed if I hadn’t said anything to you. You do what you feel comfortable with and if you decide you can’t stay I’ll understand.” In ataşehir escort bayan answer to this proposal I just leaned in and kissed Molly on the lips. As our kiss lingered I felt my cock getting hard and my desire for Molly increasing. This time when I reached out with my tongue her lips parted and soon her tongue and mine were wrestling back and forth in each other’s mouths. Molly moaned and I instinctively cupped one of her breasts. Her breasts were about a B cup and felt wonderful. I massaged her breast and weighed them both with my hands. I fondled out to her nipples and Molly inhaled sharply. I felt her hand go to the front of my pants as she rubbed my cock through my jeans up and down the shaft. Now it was my turn to moan. Molly broke our kiss and just about tore her sweatshirt in her hurry to take it off. She was wearing a sexy red lace bra which she also removed. Her tits were exposed to me now and were just magnificent. Perky and taught with nipples poking out hard and just waiting for me to suck, and that’s what I did. I took both of Molly’s tits in my hands and alternated sucking one nipple while squeezing and pinching the other. Molly threw back her head and arched her chest toward me as she moaned and said, “oh my God, that feels so good, don’t stop, harder, pinch them harder, bite them, suck them…” I did as she asked, losing myself in the intoxication that was this beautiful woman. My desire was peaking and not thinking I moved my hand down to her crotch and felt her erection! This made me hesitate as the reality of the situation hit me. Molly acted quickly, pulling my hands off her she shoved me back on the couch and unbuckled my pants. She unzipped my jeans and pulled them down to my ankles, my underwear getting caught in the motion also went down with them. My 5 inch cock sprang up at attention but had begun to soften a little when I felt her cock through her jeans. Molly didn’t hesitate she took me right into her mouth and began to suck and lick me. I was instantly harder than I’d ever been before in my life. I looked down at Molly’s beautiful face. Her eyes were looking into mine and I could see those beautiful red lips working up and down my shaft. At that moment I didn’t care if Molly was a man, a woman or a lawnmower! I blurted out, “Oh my God, I love you. I don’t care if you have a cock. I want to suck you. I want to please you!”I pulled Molly off of my cock and moved her to a standing position in front of me. I acted in a sex trance as I pulled her jeans down revealing a pair of red lace boy shorts with a cock that looked to be about 7 inches long and fully erect poking out the top of them. As I reached for her cock Molly pulled back and said, “no, not yet. Not while you’re all horny and worked up. Once you cum you might regret doing something and I don’t want that. I want you to choose to do this because you want to, not because you’re all worked up and need to cum.” “But Molly, I really feel like I want to do this.” “I know you do honey, but I know from personal experience that guys will do anything when they’re worked up, even things they wouldn’t normally think they’d do, then they cum and the regret and disgust set in. I don’t want you to regret this. I want you to do it with your eyes wide open and because you want to…”With that Molly got on her knees and took me back into her mouth. She maintained eye contact with me the whole time and she sucked up and down, up and down. She want all the way down on my shaft and I felt my cock head just entering her throat as she extended her tongue and swept it back and forth across my shaft and balls. That was just too much for me and I said, “I’m cumming.” Molly stayed on my cock but moved it to just the tip of her tongue as I shot an incredible load into her mouth. Wave after wave of pleasure engulfed me and Molly started to bob up and down on my shaft, each time she’d bottom out I could feel her swallowing. She kept it up until I was totally used up. I looked down at her beautiful face and said, “that was amazing!” then she stood up and I saw her cock still straining in its lacy enclosure.Molly was right. I no longer wanted anything to do with her cock. She was studying me carefully to see my reaction. I looked up at this beautiful woman that I wanted to love more than anyone I’d ever been with and said, “come down here and let me hold you, I just need some time to adjust.” “Well, you didn’t run out so I’ll give you that,” Molly said as she came into my arms. We kissed and I could taste my cum in her mouth. I’d never paid escort ataşehir as much attention to that taste as I did right now. I looked at her beautiful face, those perfect breasts, those long, curvy legs. I’d never done anything with another guy in my life, but I had to at least try this or I’d never forgive myself. We kissed some more and as our tongues worked against each other’s I moved my hand down to her still hard cock. When I touched the head Molly jumped. I felt the outline of her shaft held inside her panties and began to stroke it up and down gently, using just the tips of 3 fingers. I pulled the band of her pantie aside and worked my palm in and down her cock. When I reached her balls (which were mostly shrunken) I backed off a little and gave her shaft a squeeze. Molly moaned into my mouth and I could feel her body melt into mine.”What the fuck?” I thought. It’s now or never. I moved to the floor in front of Molly and pulled down her panties. Her cock sprang free and it was a little disconcerting that she was so much bigger than me. Who was the girl here? I reached out and held the base of her penis in one fist and there was still that much and a little more sticking out of my hand. Cupping her little balls with my other hand I moved closer. I really looked at her cock, the first I’d ever been this close to. There was a drop of pre-cum leaking out of her cock head slit. I took a deep breath and let it out. I looked up at Molly and saw she had her eyes closed and lips open. She was breathing deeply waiting patiently to see what I was going to do. I leaned forward and kissed her cock head and just held the kiss on the tip of my lips. I could feel the pre-cum against them and stuck my tongue out and licked it up. It tasted sweet and not at all disgusting as I’d imagined it would. I pushed forward more and took Molly’s cock head into my mouth being careful to cover my teeth with my lips — I know how much teeth can hurt! I was surprised at how spongy her cock was. I’d imagined that it would have been more rigid. Harder, with less give. Molly was now moaning loudly as I began to suck the head and use my tongue on it. More pre-cum was leaking out and there was actually enough that it was filling my mouth and I had to decide whether to spit it out or swallow it. I decided to swallow and was rewarded with an “Oh!” from Molly. This wasn’t so bad, in fact, I was getting hard again! I wasn’t really sucking a cock since it was attached to a beautiful woman, right?
I began to give Molly a real blow job, one based on all the blow jobs I’d received. I did everything I remembered that had felt so good to me. I was bobbing up and down and being careful not to gag when I got overly enthusiastic and hit the back of my throat. Molly was REALLY enjoying herself and the more she squirmed and writhed, the more turned on I became. I was getting turned on by how much pleasure I was giving her, but I was also getting turned on because I was sucking a cock! And I was loving it!Molly was really getting into it now and was holding my head in her hands. I was no longer sucking her cock, she was fucking my mouth! She was controlling how fast and how deep she was in my mouth. Every now and then I’d gag a little as she’d hit the back of my throat. One time I just felt myself consciously relax my throat muscles and she slipped into my throat an inch or so. I saw Molly’s look of surprise and a huge smile formed on her lips. She looked me in the eyes and she fucked my mouth and increased the strokes to include my now open throat. Holy shit! I was deep throating my first cock and loving it because of the pleasure it was giving my lover. Molly moaned and said, “oh baby, I’m gonna cum, do you want me to pull out?” I just shook my head “no” and began to suck harder. When she said, “I’m cumming” I did like she had done and kept her in my mouth but moved her so she was shooting directly on and across my tongue. I never wanted to taste anything so much in my life. Her cock swelled and jets of cum shot out onto my tongue. I sucked and sucked and kept my tongue working the underside of her cock head where it joined the shaft until she had filled my mouth to overflowing. Molly pulled out of my mouth and pulled me up for a kiss. We swapped her cum back and forth between us, each time I’d keep some of it and swallow it. I wanted to eat all of her cum all the time. I wanted to exist solely on her cum forever. When Molly was spent and I’d managed to swallow all of her cum she looked at me and said, “I can’t believe you did that. You’ve never sucked a cock before?” “No, never. I love you Molly and want to please you in any way I can.” Molly was crying now, “Oh Kevin, I love you too. I can’t believe I’ve been so lucky to meet a man as perfect as you.” …Molly and I got married a week later and have never been happier!

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