How I Met Alyssa


Author's notes: This is my first story. Any feedback would be greatly appreciated, since I'm still learning the ropes. This story is about a romance between a man and a shemale, if you do not like this, you should click 'back' on your browser. If this story is well received, I might bring up a sequel, I already have some ideas, but feel free to bring up any suggestions.


I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up.

I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year old guy, senior in college, average sized body with short, brown hair and green eyes. Now the academic year has ended a few weeks ago, so why would I feel the need to get up so early? Well in fact I have a date in few hours. Although I should mention that this isn't your typical date, where the guy picks up the girl next door and they go to see a movie.

A few months ago, I met a wonderful girl on a dating site. I know it's not really the classic way of meeting people and it's not my preferred method of getting to know someone either, but since I am shy with people I don't know, I figured I'd give it a try. Like I said, I met a girl on there, a really cute one. She has long black hair, olive coloured skin and from what I've seen a nice figure. Her name is Alyssa and she immigrated from Italy. She has a body that would please most men, but like me she was also pretty timid around people that she didn't know. Ever since we met, we've often been chatting, sometimes for hours straight. Sometimes we put our webcams on, eventually even exchanged phone numbers. I really felt like we had a connection from the start and still have it by the way. Making a conversation with someone was never really easy for me, but with her everything felt natural and relaxed.

We've talked a lot with each other, joking, talking about our day, sharing secrets, etc. One of those secrets was that she was actually a shemale. She told me so one night when we came to the subject of sexual fantasies. I told her that being with a shemale was one of my fantasies. A night with a shemale would be like a dream come true, although it didn't necessarily have to end after that, which I also told her. She seemed particularly interested and after a little conviction on my part as why she was so interested, she confessed to me, that she was actually a male-to-female transsexual instead of a regular girl. Although it's not like I ever would have guessed. She was feminine in every way possible, well except for one I guess. We talked about it for a while and told me that she really hoped that I would still treat her the same way and as a woman. To me that was only natural, as she was still the same person I cared for and at that point, about to fall in love with. She told me about some earlier encounters with people and their reactions after she told them her secret and I can't say I blame her for her precautions.

Anyway after that little chat everything changed -- in a good way. Before that little revelation we occasionally flirted a little, but nothing big, more like teasing each other a bit. But I mentioned that our manner of talking, the flirting and all that had changed. we started liking each other more than just really good friends, we started viewing each other as potential partners. As we grew even closer, I suggested to meet each other in person. She was a bit reluctant, as it would be a huge change in our relationship, one that may not be reversed if it turned out badly. Although she admitted she had also thought about it and would like to meet me as well. She lived in a city called Brighton -- a city she chose for its good location, vacant property and its acceptance of transgender people. I lived in a city called Basingstoke, which is about 85 miles further or a 2 hour drive. We agreed to meet somewhere in between, so the drive was acceptable for both of us and have a bite and a drink at a local restaurant.

That date was due in a few hours, so I prepared myself, taking a shower, combing my hair, putting on a little aftershave. While in the shower, I felt my cock stir a little at the thought of Alyssa. I couldn't help myself but start thinking how we could make love all day, if the date had a typical perfect scenario, but one can dream, right? It made my six and a half inch rod harden. I thought about pleasuring myself quickly, but decided against it. I definitely didn't want to be late because I was masturbating in the shower. Right now I got out the shower, dried myself and gave my hair a nice, finishing touch. I went to the bedroom and picked a nice outfit. We had told each other our outfits beforehand, so that we could recognize each other. I was to be dressed in jeans, a white shirt, a blue jacket and black shoes. She would be dressed in a white summer dress that went to her knees, with short sleeves and black heels. I picked out my clothes, had some breakfast and I saw that it was time to be on my way.


I arrived at the agreed restaurant, a classy little place. I went inside, looked around and could see no black haired girl with a white dress. So I decided to get a table for 2 and ordered myself a drink. A waitress arrived to take my order. She didn't look too bad, blonde hair, blue eyes, cute smile -- a college student like me I guessed.

After a few minutes of waiting I saw a girl entering the restaurant. She wore a pearl white dress, under that she had long, smooth legs. She had beautiful, long black hair that went just past her shoulders and crystal clear, blue eyes. Through the dress I'm pretty sure I saw a sweet bubble butt, a perfect set of breasts -- B cups if I would have to guess. When she saw me, she gave me a nervous, yet the prettiest smile I've ever seen. If angels walked on this earth, this was definitely one of them.

She approached me and asked in a semi-nervous way, "Hello, are you perhaps John?" I stoop up as to be polite to this girl and said, "Yes, I am John. You must be Alyssa?" I extended my hand to greet her, but she closed the distance between us and hugged me, giggling a bit. I felt pretty embarrassed, this was our first date and I already made a fool out of myself. But then I felt her warm body against mine, her soft skin felt so nice. I could smell her perfume and I forgot all about my embarrassment. I felt my cheeks go red, a smile grew on my face and I knew I was falling in love.

"Yes that's me," she said while separating us. I looked into those eyes again and I knew it for sure, I was in love with this girl. She took the seat opposite of mine and said, "I'm glad we finally get to meet each other. Have you been waiting for a long time?"

I have to admit, I was afraid that our conversation would be a little less fluent, cramped, maybe even forced. But we quickly started talking about lots of stuff, even though we'd already talked so much in the past. We were both a bit nervous in the beginning, but we managed to keep the conversation flowing, the mood positive and our nervous manners soon disappeared. The waitress brought me my drink and took Alyssa's order as well, but I barely noticed her. I started talking about my upcoming final year in college and she talked about her job. She is the personal assistant of the CEO of some big accounting company. Being the right-hand of the CEO meant she often knew sensitive information. Her boss made sure to keep her happy and well compensated, so that nothing would mysteriously or accidentally leak to competitors.

"So, how was your week at work? Has your boss softened up a bit since last week?" I asked. The previous week she made a little blunder at work, that caused a lot of inconvenience and her boss was pissed off about it.

"Yeah, luckily for me she has. Things were back to normal after a few days, " she explained, "You know, she was particularly interested when I spoke of our upcoming date. She said she was glad I finally met someone special and didn't lock myself up anymore."

"Ooh I'm already someone special huh?"

"Hey, those aren't my words," she laughed a bit and took a hold of my hand, "but yes, you are special to me." She looked deep into my eyes and I could see the love in them.

I couldn't help the smile that appeared on my face and said, "Well, I can say the feeling is mutual," and I covered our hands with my second hand, she did the same and now both our hands were intertwined. We were looking into each other's eyes, like teenagers obsessed with puppy love

The waitress arrived to take our orders regarding our main course. I chose a steak with some French fries and she chose a salad. "A woman has to watch what she eats or her belly would soon expand more than you'd like," Alyssa said. I decided to try charming her a little and said, "I can't imagine you being anything resembling fat or even unattractive," and I tried to give her a little wink, although it kind of failed, but she didn't seem to have noticed.

She giggled a bit and said in a soft voice, "Aww thank you. You're really sweet."

"Anything for the ladies," I joked. Even though right now there was only one lady on this planet for me.

Our lunch arrived and we generally had a good time, talking, laughing, flirting with each other. We continued to chat for what felt like minutes, but before I knew it, it was 2 hours later. "Oh my goodness, is it already this late?"she said.

"Yeah now that you mention it, time sure flies when you're having a good time," I responded.

"Yeah it sure does." I asked a waitress for the bill and paid for both of us. I figured that'd be the best, since 'the guy always pays'. Not that I mind and I could tell by Alyssa's facial expressions, she was pretty happy with being treated this way.

We left the restaurant and went to our cars. We stood in front of her car, when she said, "I really had a good time John, I'm glad this date turned out so well."

She leaned in a bit and I could tell she wanted to kiss me, but she still had that final barrier of shyness, that prevented her to go for it. I decided to just do it. I took her chin into my hand and pulled her face closer to me, while leaning in myself. I could feel her tender, soft skin, I could smell her perfume. Even after about 3 hours it still made my heart beat faster. I quickly closed the gap between us and pressed our lips together. She immediately returned the kiss and I could feel her hot lips pushing against mine. I closed my eyes and I felt like I was in heaven. I cupped her head in my hands and put all of my passion into the kiss and she fully returned it with just as much passion and desire as me. Now these were the fireworks people were always talking about.

Finally after what felt like ages, we separated while still looking into each other's eyes and with a smile appearing on our faces. I tilted my forehead a bit forward and she did the same so we were connected that way. "That was nice," she said.

"Sure was, felt good too, " I responded

"Mmmmhmmm," she groaned.

This time she took charge and leaned in once again. She started kissing me hard on the mouth taking my head into her hands as I returned the kiss. I felt her tongue licking my lips and I opened up so our tongues could touch. Immediately our tongues started playing with each other, duelling with each other, touch-and-go or just wrestling with one another for as long as possible.

After what must have been a few minutes, we separated once again and I saw her grinning. 'Damn,' I thought, 'maybe she secretly has a bit of a dominant side.'

"I should get going, it's getting a bit late," she said, still with that cute grin on her face, "promise to give me a call?"

"I promise," and I gave her another peck on the mouth.

With that she got in the car, gave me one last wink and drove off. I stood there, grinning like an idiot, thinking about what a wonderful afternoon it had been and I knew I was in love.


Remember how I previously told you things got better? That was good. Now things got better again and now it was incredible. We started talking to each other the way 2 teenage lovebirds do when they're split up for the weekend. We started texting each other more often. Most things were actually quite silly now that I think about it, like saying how much we miss each other, how much we love each other, ... .

After about a week, she asked if I wanted to come over for a drink. Needless to say, I accepted. I really wanted to spend more time with my Italian angel, plus I didn't really have anything better to do.


The big day arrived and I drove over to her house. For the past days I've been trying to improve my Italian speaking skills a bit, well more like creating them. Since I hadn't spoken a word Italian until recently. I worked a bit on the most basic words, verbs and a few ... particular things. I also wanted to bring a little gift for her, because of the invitation, because of us. I decided to bring her a bouquet of roses, bit of a classic choice. But I'm fairly sure she once mentioned receiving flowers for something and she liked it, if I recall correctly.

I arrived at her house in the afternoon and got out of the car. It was a pretty nice house, a large Victorian house. The pay of a personal assistant must be pretty good, if she could afford this on her own.

I rang at the door and after a minute or two she opened it. I was once more surprised by how gorgeous she looked. She was dressed in a black off the shoulder top that hugged her breasts, her shoulder was mostly covered by her hair. Her legs were covered in some light jeans.

"Hey John, glad you could make it."

"Buon giorno Alyssa, glad I'm here," I said with a grin on my face, my eyes never leaving her body.

A look of surprise appeared on her face. "You never told me you speak Italian."

"Well, I don't really. I just tried to learn the most basic stuff, thought I'd try to surprise you, you know?"

"Consider myself pleasantly surprised and yourself in for a good, second date," she said, still with a grin on her face. "Are those for me?" she asked, sounding slightly surprised again. Her eyes were focused on the bouquet roses.

I gave her a smile and said, "Ow these? I brought them for the prettiest girl in the country, so here I am." And I handed her the roses.

She bit her lower lip in an attempt to hide her excitement. She quickly took the roses with a big grin, "Thank you!" She said, taking a good look at the roses. I bought them on the way here, so they were still fresh and healthy. Then her focus went back to me and said, "Anyway are you going to stay outside and keep staring at me or are you coming inside?"

I went inside and said, "Sorry, didn't mean to stare. I was just admiring your outfit."

"You like it?" she asked and came closer to me.

"Sure do, really accentuates your body," I kissed her on the lips, "not that your body needs it."

"Charmer," she said with a smile. "Come on, let's go to the living room and have a drink."

"Living room? I thought we were going straight to the bedroom?" I joked.

She chuckled and said, "Not yet sweetie, maybe later if you behave or if you get me a bit drunk."

"Or both," I mumbled, loud enough for her to hear.

She giggled, but didn't respond. She just moved further in the hall and said, "anyway, this is the living room, what would you like to drink?" Meanwhile she grabbed a vase and put the roses in them.

"Uhm, you got some cola?"

"Of course," she quickly went in a room nearby -- the kitchen I presumed -- and returned with 2 drinks. We sat down on the couch and started chatting.

"Nice place you got here by the way," I said.

"Thanks. I bought it with a mortgage about a year ago. I loved it, the moment I saw it. The house looks good, plenty of space, a small garden, not that far from the beach, even the neighbours are really nice."

"That's really cool. If you don't mind me asking, how could you afford it? No offense."

"None taken, well my job pays pretty good, aside from those occasional benefits I told you about, plus it also helps if one of your colleagues can put a good word for you."

"Ah yes, that's convenient. Ever get lonely in a house like this?" I blurted out.

Her face saddened a bit and I kicked myself for asking such a dumb question, "Sometimes, a bit. I mostly missed some company, someone I could talk to when I had a bad day, someone to hug tightly when I was feeling ecstatic, someone to ... share my life with."

"Aw shit, sorry Alyssa, I didn't mean anything by it. I didn't want you to think about something like that. I'm sorry, it was a dumb question." It really broke my heart to see her so sad, I sat closer to her and put my arm around her.

"It's okay, " and a faint smile appeared. "It's gotten much better since I've met you. You were always there when I needed someone to talk to. It was almost as good as you being beside me."

I held one of her hands in mine and put my other hand around her neck, embracing her. I looked into her eyes. "Well, I'm here now and I don't plan on leaving you anytime soon," I said.

She didn't say anything, I could see her eyes moisten a bit, as if she was going to cry. She just smiled and moved her face towards me, kissing me. After a few minutes we pulled apart and I could see a tear rolling from her eye. I could see her lip trembling a bit and her eyes were a bit moist.

"Aw c'mon, are you crying?" I asked with my sweetest voice.

"I'm sorry John, I jus-", I broke her off with a quick kiss. "Don't be sorry."

"It's just that I'm so happy that I found someone like you. Someone to love me for who I am, someone that looks further than my looks or my 'condition', someone to ... share my life with."

I cupped her face in my hands, rubbed the tears off her face. "Alyssa, please don't ever be ashamed again of who you are. You are a strong, independent, gorgeous woman. It's a privilege to know you so well and I admit, I feel the same way. I feel blessed having met you. You are one-in-a-million."

Her smile widened. "Do you really love me that way?" She asked, as if she almost didn't believe what she was hearing, needing to hear it again.

"I do baby, I really, really do. When I see you smile, I am the happiest man in the world and I could take on the world. But when I see you cry, it makes my world fall apart and it makes me feel horrible. I could not ask for a better girlfriend."

"Girlfriend huh? Who says you're already that far?" she teased.

"I think I have a pretty good idea about how far we are right now," and with that I pushed our lips together. I pushed my tongue against her lips and she opened her lips without hesitation. Our tongues started wrestling.

While French kissing, our hands started moving. We were gently stroking each other, arms, necks, hair were all being fondled. After about a minute, she broke off the kiss and gently pushed against my chest, pushing me on my back. My upper body lowered, going from a sitting position to laying down. She crawled up to me, straddling my stomach, moving the way a predator goes to its prey and from the look in her eyes, I was on the menu.

We started kissing again, with Alyssa definitely taking charge. She stroked my chest, while she sat upward, looking down on me as if to show me who was in control. I could feel my cock start to harden.

'Someone came out of their shell,' I thought as I eyed her. She was clearly enjoying this.

She took my hands and placed them on her breasts. "Come now, don't be shy my love," she whispered. Needing no further encouragement, I started fondling her breasts. I massaged them, squeezed them, tried to pinch the nipples a bit through her shirt and bra.

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bythatlonewolf© 18 comments/ 118736 views/ 127 favorites

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