17 comments/ 91106 views/ 84 favorites How I Met Alyssa By: thatlonewolf 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. How I Met Alyssa "Mmmmmmm," she moaned. She was biting her lower lip, showing me how much she liked it. I moved one of my hands to grab a hold of her ass and started rubbing it through those tight jeans. "You like my body? You can play with it all you want, you know," she said with a cat-like grin on her face. I continued to massage and grope her body in all the right places. I tried to move myself up a bit, so I could kiss her again, but due to our sizes I only got to her breasts. Not that I complained, the view was certainly nice. I placed a soft kiss between her boobs and said, "There's something in my way, mind if I take it off?" "Go ahead" and she lifted her arms up. I grabbed the bottom of her shirt and pulled it over her body, revealing a red lacy bra. My eyes widened at the sight of the bra and I gave a wolf-whistle. For a minute, I was staring at her tits, seductively tucked in the garment. "You know, this thing can come off, right?" she said with a hint of sarcasm. "I'm sorry, what was that?" I said, grinning, as I made no intention to do something. Alyssa sighed heavily in a playful manner and reached around to unclip her bra. "men," she muttered. "Hallelujah!" I said, with some weird voice, that surprised even myself. I was now staring more than ever at those perfect round tits. I reached for them and took them in my hand. "This is a really nice pair," I said, almost with admiration, "fits perfectly in my hands." "Glad you like them," she said, sticking her tongue out, "because you will have to play with them for a long time." "I sure hope so," and I squeezed them, they were so soft, yet so firm. By now I was completely hard and my cock was straining against my jeans, begging to be released. Alyssa moved a bit backwards, sitting with her ass on my crotch. I felt my erection straining against that sweet ass, which didn't exactly help my current state. "My, my, someone's a bit eager," she said as she grinded her ass against my bulge. "Mind helping?" I managed to say. This whole thing had me a bit paralyzed. She lowered her face, her mouth to my ear and whispered, "How can I help, my love?" "Surprise me," I whispered. In my current state I wasn't really capable of saying more than a few words. But luckily what we were about to do, didn't involve a lot of talking. She reached down and unbuttoned my jeans, but instead of lowering my pants, she took off my shirt. Now we were both topless and our breathing had gotten a bit heavier. Our lower bodies were somewhat pressed together, she still straddled me in a reverse cowgirl position. I could see a nice big bulge, despite the jeans she was still wearing. This instantly increased my lust and with a predator look of my own, I eyed the bulge of her erection and rubbed it through her jeans. While my hands were taken care of her lower equipment, Alyssa's hands stayed high and massaged her boobs, eyes closed and head thrown back, clearly enjoying every minute of it. "Mind if I take this off as well?" I asked, my hands tugging the waistband of her jeans and rubbing the front to emphasize my point. "God I thought you'd never get to it," she says in a sultry voice, "you terrible tease." Despite wanting to get both of us off, I couldn't resist teasing her just a bit more, "did I say I'd take them off? I meant play with your boobs a bit longer," I said with a grin on my face and my hands went back to her breasts. "Damn you're terrible," she said in a somewhat annoyed voice. She got up and kneeled down, "if I'd have to wait for you to do this, we'd be like this for hours, either with painful hard-ons or having jizzed in our pants." And with that she crouched a bit to take off my pants, I lifted my butt to make it easier. She threw my pants on the floor, leaving me sitting on the couch with a tent in my boxers. She started to slowly move in front of me, like a lap dance. I watched her figure move slowly and my dick was at full erection, to the point where it was getting painful. I reached for it so I could give myself some relief by releasing my cock from its little prison, but Alyssa's hands stopped me and she made a disapproving noise. After what felt like half an hour, but was probably no longer than a few minutes, she finally took off her tight jeans slowly, sticking her butt out to me. 'God, what I wouldn't do to get a piece of that ass,' I thought. Luckily I'd only have to be patient as her pants dropped the floor. There she stood before me. In a proud, feminine stance, naked except for some pink panties. Panties which had a pretty big bulge in them. My eyes widened at this incredibly erotic sight and Alyssa laughed softly as she saw my reaction. "Like what you see sweetie?" she asked. "Yeah ... you could say that," I said, my eyes glued to her crotch. She once again reached down, this time to take off my boxers and in one swift motion they were off and my cock was finally freed, slapping against my belly. The relief I felt was incredible and I could see a tiny bead of precum at its tip, as well as another drip near my belly button. Alyssa's hands reached down to her pink panties to free her own straining cock, but as soon as her hands clasped the waistband of her panties, she hesitated for a moment. I lunged forward and quickly shoved her panties down. Her cock instantly sprang to life, almost smacking me in the face which made her giggle. It was pretty big or at least looked pretty big. Bigger than mine I'd say, something that only turned me on even more. I was staring at her cock, admiring it. "nice ... equipment you got there," I said without breaking 'eye contact'. Alyssa smirked and said, "thanks yours is pretty nice too." I looked up and saw she was staring at my member as well. "Maybe we should compare sizes sometime?" I asked. She looked down and grinned. "I prefer to measure them with my mouth" and with that she pushed me on the couch and kneeled in front of me, my cock in front of her face. 'Damn this girl is kinky and dominant,' I thought to myself and I loved it. She stared at me with those puppy eyes, as if waiting for my permission or an order. Or she was just being a terrible cocktease. Finally she licked the head of my cock. After giving it a few licks, she took the head completely in her mouth, sucking and licking on it, earning a moan from me. 'the first of many', I thought. She took the head out of her mouth again, which made me look down at her. My cockhead was shining with her spit and the look on her face made my cock twitch. With a big grin on her face, she gave my entire cock long licks, starting at the balls and slowly going up to the top, after which she returned to the base. I clenched my teeth, damn this felt good. I had received a few blowjobs before from other girls, but none of them were as good as this one, not even remotely. This girl really wanted to please me, to make me feel good instead of just wanting to get the blowjob over with. After she gave me a few long licks, she remained at the base and licked my balls. I had shaven them and every other important spot on my body yesterday, just in case. She licked them, took one of them in her mouth, sucking on it. After a while she switched and handled the other one, earning soft moans from me. "Baby, you do that so good ... I never want this to stop, I always want to be with you" I say. she came up to my face, leaving my rock hard, wet cock for what it is. "You really mean that?" she asked, apparently still unsure now that I bring up emotions again. "of course I do baby, you're awesome and I love you and I want to show that to you," I tell her while looking deep into those blue eyes. "can I repay the favour?" I ask, my hand finding its way to her own straining cock and giving it a few strokes. Her face lit up and she immediately said, "would you -- I mean yes please!" I smirked at her reaction. I switched us around a bit, so that she was now sitting on the couch and I was kneeling on the floor between her legs. "can I suck your cock baby? Can I lick your cockhead?" I asked her with a grin, my face barely an inch apart from her cock. Damn, it looked so good, so perfect, throbbing hard, a drop of precum on the tip from all the excitement and such an enchanting, erotic smell. She squeezed her eyes shut for a moment, apparently she isn't one to be teased, "God please do!" She says quickly and then looks back at me. I smile and nod at her, no longer planning to tease anymore. I grab the base of her big cock and start to lick the head, earning a moan from her. Satisfied with her moan, I continue enthusiastically licking the head, slowly bringing my mouth closer, until I kiss the head. I taste a hint of precum and I kinda liked it. It was a bit salty, but definitely not bad. I start to suck on the head of her cock as best as I can. I want her to have just as much pleasure out of it as I just had, if not more. I started bobbing my head up and down on her cock, gradually taking more and more of her cock in my mouth. Every once in a while I got a moan out of her and every time I repeated my last action or sucked a bit harder. After a while my lips were almost at the base of her big dick, but I had trouble getting the last few inches inside me. 'must be my gag reflex or something,' I think to myself. It doesn't stop me from sucking and milking the other three quarters of her dick. While I'm working on her, I start stroking my own dick down below. It was still covered in Alyssa's spit, which served as excellent lubricant and it drove me crazy. I felt myself getting close to orgasm and I heard Alyssa's breathing quicken as well, less controlled, so she must be getting close as well. I wanted to double my efforts, but suddenly her hands lifted my head and I had to let go of her delicious cock. "what's the matter? I thought you were getting close?" I asked, a bit confused. She gave me a big smile, "I was and you did a wonderful job." I opened my mouth to say something, but she hushed me with a finger, "but I want us to finish in another way." Her smile grew wider, "I want you to finish inside me." My eyes grew wide for a second and my mouth probably hung open. "you- you want me to-" "fuck me in the ass," Alyssa finished for me, still with that grin on her face. She made both of us stand up and pushed us together, making our hard cocks slide against each other. "don't tell me you don't want to fuck my sweet, tight ass," she said in a seductive voice and placed one of my hands on her ass. I gulped, where the hell did sweet, innocent Alyssa go and who is this little nymph in front of me? I got a hold of myself and replied, "well if you insist, I'll have to comply." I kissed her deeply on the lips. "Mmmm," she moaned into the kiss. "That's more like it, pretty boy," she said as we separated. She looked down at our throbbing, wet cocks and said, "mmm, not bad, but I'll quickly refresh the lubricant, okay?" and without waiting for my reply, she dived down and took most of my cock in her mouth in one swift motion. It made my eyes widen again and making me moan softly. After going up and down a few times, she got up again and made a disapproving noise again. "I told you, you naughty boy. I want us to finish with you inside me," and she gave me a quick peck. "now why don't you prepare me for you big monster?" she said, while turning around and bending over, exposing her sweet little asshole. At this point I was way too horny to think about it. I immediately went on my knees and buried my face into her ass. I grabbed a hold of her ass cheeks and immediately started licking. I heard a faint moan when I started, damn this girl is horny. The taste wasn't even as bad as one would expect. Either I was so damn horny or she must have cleaned herself thoroughly beforehand, probably both. I continued happily licking her little asshole, while both my hands fondled her dick and balls. Her dick was still very wet and only then I realized I forgot her cute, little balls earlier. I decided to make up for it and fondled them with extra care, massaging them while I inserted my tongue in her ass. After good few minutes of eating her out like that, she stopped me again. "Okay I think that's enough. You'd have me blow my load every time you started something if I didn't stop you," she said as she turned around again. I shrugged with a grin on my face, "what can I say? I aim to please miss." It really was nice to see I had this effect on her. I stood up again. "actually I'd prefer Mrs. Now that you're here," she says with a grin. "now enough fooling around, I want to cum and I want to cum really good," she says as she bends over the couch, exposing her ass to me. "of course Mrs," I say. I grab her by the hips and position my cock against her moist asshole, "want me to go slowly at first?" "yeah," she stammered while grabbing a firm hold of the nearby pillows. I pushed my cock into her asshole slowly. It went in quite smoothly, thanks to plenty of lubrications on both sides, but I still went slowly at first. "Damn you're tight baby," I whisper as I push in further. "Oooh, it hurts a bit, but it feels so good," she replies in a soft voice. I kept pushing inside her, until I was finally about three quarters inside. It kinda felt like I had bumped into the end and when I did, I earned a gasp from her. "You okay baby?" I asked, leaning over a bit. "Mmm yes, it feels kinda nice, wait a minute" she says. I complied and just kept my cock unmoving in her, so she could get used to it. "Okay, you can start baby," she said after a while. Finally. I grabbed her hips again and started fucking her, slowly at first. I definitely didn't want to hurt her or anything like that. I rocked my hips back and forth, "Mmmm harder!" she said. I smiled and complied, thrusting into her harder and faster, making both of us moan. "God yes!" she said. One of her hands went to her boobs, playing with her nipples, while her other hand maintained her balance. I decided to help her a bit and let one of my hands go lower. I grabbed a firm hold of her cock which was swinging wildly back and forth in front of her in time with my thrusts and started jerking it wildly, together with my thrusts. Alyssa let out a little gasp, "ooh yes! Jerk my big cock, while you're fucking my tight asshole!" I let out a loud moan and increased my efforts, both in jerking and fucking, "You're so hot Alyssa! I wanna fuck you all day long! I wanna make you cum over and over again!" After a few minutes of doing this, I felt myself getting close. Usually I lasted a bit longer, but due to all the foreplay and fucking such a smoking hot woman, I should be glad I lasted as long as I did. "Baby I'm getting close," I grunted. She groaned, "Me too! Let's cum together John!" I gave a few final, hard thrusts into her ass and that pushed me over the edge. "I'm cumming!" I cried out and I started shooting jets of hot cum in Alyssa's ass. As I was cumming inside her, I heard her faintly say, "me too!" and I felt her dick contract as well. She shot plenty of cum on the couch, while I filled her ass and gave a few final thrusts. As our orgasms subsided, our breathing slowly became steady again and our muscles relaxed again. I said in a soft tone, "That was ... so good." Alyssa giggled, "Yeah it was! I don't think I ever had such a nice orgasm." "Must be the company," I cheekily say, leaning down and kissing her neck. She turned her head and we kissed each other again, with my dick still in her ass. After a few kisses, she gave me one last peck and I took my member out of her ass with a 'PLOP'. She turned around and sat beside our earlier spot. I looked down and saw the huge puddle she made. "Wow! You made a big mess," I say, a bit astonished. I turn to look at her and see she's smiling just as widely as I am. I even notice a bit of my cum leaking out of her ass. "must be the company," she purrs and she grabs my hand, pulling me down. We lay together like that for a while, enjoying the afterglow of our lovemaking. Her head laid on my shoulder and my fingers traced and tapped her body a bit, while she rubbed my chest. "Wouldn't mind doing this again," I whisper. "Me neither," Alyssa says happily. My fingers playfully ran down her body, poking her belly button, which made her giggle. Finally I tapped her semi hard dick softly, I rubbed it and felt it react to my touch. "Someone's horny," I whisper. "Mmmm, can't help it. It's your fault. You're doing this to me," she said. I chuckled, "yeah blame it on me. But then again, you just came wildly and you're hardening again. Do you have that big of a libido?" She looked up and smiled, "Maybe I do ... and I also have a hot boyfriend, who does nothing but tease me and make me want to fuck." She gave my neck a soft kiss. "well ... if you insist I suppose I could always stop..." I said, even though I didn't plan to. She turned her head a bit and gave me a peck on the lips, "No need to change baby, I already love it." I chuckled and my focus went back to idly playing with her body. I noticed it shined a little, must be from the sweat and our 'workout'. "You know, you could use a shower" I whisper. She turned to look at me and I saw she was beaming again, "So could you." With that said, she got up and extended a hand to me. I accepted it and got up as well. I grabbed her hand and followed her upstairs to her bathroom. On the way I noticed my first impression was about right, this place was pretty fancy, for a single person at least. It wasn't over the top luxury, but you could tell money wasn't a big concern. We got in the bathroom and I took a moment to observe it. It was quite nice, mostly white or pink colours. It had everything a bathroom needed, two sinks, a bath, toilet, shower. It was definitely enough to put my little college apartment to shame. I turned to look at my new girlfriend and saw she was leaning with her back on one of the sinks, with an alluring look on her face. Her crotch stuck out a little, due to her position, but I doubt either of us minded. "Like the place sweetie?" she asked. I nodded in agreement, "Definitely, wouldn't mind coming over here more often." "And who says you'll be allowed?" she leaned forward with a smile. I leaned in as well, closing the distance between us, "Well actually, I'm the new boyfriend of the landlady, so if I ask her really nicely, I think I'll be allowed to come over here once in a while." She pressed our foreheads together, "Well if the landlady approves of you, I'm sure it'll be okay. She told me you were a great fuck by the way." "Has she now?" I ask, trying to sound as if I'm shocked, "well I'm sure she told the truth, I definitely didn't hear no complains." "Mind proving it to me handsome?" she teasingly asked, pressing our lips together briefly. "Not at all honey," I said, returning a quick kiss. I quickly come closer to her and trap her between myself and the sink, making her gasp. I press us tightly together, the wonderful feeling of our cocks pressed together, a little higher her boobs press against my chest and at the top our lips are joined together. She pulls back, a lustful look in her eyes, "C'mon let's shower baby," she says. I quickly look around to see the shower and find it. I grab her hand and lead us to the shower. We get in and it's quite spacious for a shower, room enough for two. She starts the shower and we have a fun time washing, fondling and playing with each other. After a while we're pretty much clean and we just spend some time fondling and groping each other's body. Suddenly her finger traces around my ass making me jump a bit, "What's the matter John? Don't like it in the backdoor?" I straighten up a bit, "No it's not that, just a bit surprised. Why do you ask? Interested in my backdoor?" How I Met Alyssa She gives my ass a little slap, "Of course, you got mine, so I'd like it if I can have yours, unless-" "Don't worry Alyssa, you can use my ass all you want," I interrupt her, "like you said, it's only fair and I am quite ... curious about it." Her smile reappeared, "Good, I'd like to try that with you. Are you ... clean?" "Yeah, I happened to clean myself before I went on my way," I reassured her. "What a coincidence huh?" I asked with some sarcasm "yeah, unbelievable," she answers with a smirk, "now bend over. I wanna inspect the goods." Her forwardness made me smirk, but I was happy to comply and bended over. "be gentle with me my love, it's kinda unused so far," I said. I hadn't had anal sex before, well not on the receiving end anyway. "Owww, you remained a virgin for me down there?" she said in a naughty voice, her finger rubbing around my ass, while the water was spraying against it. The stimulation made me moan a bit, it felt kind of nice, "Yeah, just for you, for your pleasure." "Hold up, if we're gonna have some fun like this, I'd prefer if we did it somewhere else," she suddenly says. I looked back, "What? I thought you wanted to fuck me?" I asked, a bit confused. "Don't worry baby, I will, but I'd prefer if we did it on my bed, more comfortable," she says. I nod and agree with her. We get out of the shower and dry ourselves off, doing our best to ignore our boners. I am about to ask what clothes we're gonna wear, but quickly realize it's a dumb question, as what we're doing doesn't require any clothes. We quickly get out of the bathroom, dry, clean and ready for more action. Alyssa leads me to her bedroom and I'm once again a bit surprised by her house. It's kind of what I expected of her, a big bedroom with a king size bed. It could be easily be described as 'girly', but not enough that its childish, just feminine I guess. This time I don't lose much time staring at the furniture and simply join her on the bed. At the moment we sit next to each other, looking at the other one. "Ready for some more fun?" she asks excitedly. "Sure thing, how do you wanna do this?" I ask her She thinks for a moment and then gets an idea, "I know! How about you lay on your back and I lay on top, we blow each other and I also prepare your ass as well. After that I can fuck you alright?" Wow she sure is enthusiastic about this, but who am I to complain? "Sounds good baby," I tell her, giving her a smile. I lay down on the big bed, waiting for her to join me. She turns herself in the right way and crawls over me. I see her flaccid penis hanging in front of me and it was pretty hot. Alyssa didn't waste any time and immediately went down to business. She took my also soft dick in her hands and start licking it. I was uncircumcised, so was she by the way, and her tongue felt pretty good like that. I was almost too lost in my own pleasure to realize I had a job myself. I grabbed her ass cheeks and pulled her closer to me, taking her entire dick in my mouth, balls deep. Her balls almost rested on my nose, and I happily licked her entire dick in my mouth. I felt her dick gradually grow and harden in my mouth, to the point where I had to release it. By now it was about the same size as earlier, completely erect. I still had some trouble taking it completely inside me. I make a mental note to 'practice' a bit in the future, one way or another. On the other side of the 69, Alyssa sucked me to full erection as well. My cock was once again throbbing hard and ready for more action. Too bad I was going to get a bit less. She bended my cock and lowered her face further. She briefly licked my balls, a few long licks, but soon lowered herself further. I felt her hot tongue on my asshole, which made me moan. "ooh damn, that feels ... kinda nice babe," I whisper around her cock. She grabs my ass cheeks and spreads them to have better access, "Nice feeling isn't it?" and she goes back to licking me, preparing me for the upcoming fuck. While sucking her cock, I notice her tongue movements are similar to mine earlier. Either It must have felt really good or my I must be a natural. I squeezed my eyes shut for a moment, when she inserted her tongue inside my little asshole. I wanted to moan, but couldn't because my mouth was full of her dick at the moment. I didn't bother getting her out of my mouth, just kept on heavily sucking and licking her cock. After another few minutes of sucking and licking each other like that, she lifted her head and said, "I think that's enough baby. You're wet enough and I don't wanna cum in your mouth." I got her throbbing member out of my mouth, "Ok." She rolled off me and I got on all fours, my ass pointing at her. "Like this baby?" I asked. "Perfect," she simply said, her hands grabbed my hips like I did earlier. It made me cringe a little, as I'm not really used to being handled this way. "You okay baby?" she asked. "I'm fine, go ahead," I assured her. I didn't hear anything else from her, but prepared myself for what's coming. I feel her cockhead prodding my ass and with a swift push, she inserts herself in me. It made me cringe a bit, but after a combination of slowly going further and stopping to let me get used to it, she's soon balls deep in my ass. She lets out a little moan as she reaches the end and I bite my lower lip. Damn this felt pretty good after the pain subsided. She waited a minute or so and asked me if she could continue. I turned my head and nodded. She slowly started fucking me, going back and forth. I grunted lightly every time she smacked into me. it started to feel pretty damn good, her dick going in and out of me, rubbing against my prostate. One of my hands reached down and I started to masturbate my dick, while my girlfriend was fucking my ass. "Mmmm fuck me harder baby," I whispered, pushing my ass against her at the right times. "Alright sugar," she said and I felt her thrusts started to quicken. Her balls were smacking against mine and we were both sweating and moaning. "Damn you feel so good baby," she says. "So do you, I love being fucked by your big cock," I manage to reply. We continue like that for a long time, her fucking me and me jerking my own dick. We both manage to last a little longer, thanks to our recent orgasm. But after a while I can feel my upcoming orgasm again. "I'm getting close," I whisper, barely understandable. Her hand reaches down and joins mine in jerking. She leans down and whispers in my ear, "Cum for me baby. Shoot all of your hot cum out while your new shemale girlfriend is fucking your ass like crazy." Hearing this triggered my orgasm. I clenched my teeth and squeezed my eyes shut. I tensed up for a moment and started cumming. I shot jets of cum onto the sheets of the bed. Cumming like that had worn me out and I let myself relax a bit, but apparently Alyssa wasn't far behind. "Cumming!" she shouted and after a few more hard thrusts, I felt her shoot her hot cum inside me as well. She lowered herself on me, more like softly falling on me. I lowered myself as well, causing my chest and belly to drop in my own puddle of cum, but I didn't care at the moment. Alyssa lay on top of me, her cock still in my ass, nipples pointing in my back and her heavy breathing in my ear. It took us a few minutes to catch our breath and when we did neither of us moved. "I love you John," she whispered in my ear. "Ti amo troppo Alyssa."