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Losing my Trans Virginity

I was 18 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Even watching shemales, got me extremely excited because I did not think of them as guys. I thought of myself as a decently attractive guy, not "hot" by any means but definitely not ugly either. I was athletic and took care of my body so I couldn't understand why I couldn't find a girl who would have sex with me.

I had just moved to a new town far away from my old high school and did not know anyone. I had a girlfriend before I moved but all we had done together is use hands and dry hump, no matter how hard I tried to convince her to have sex. When I moved away, we broke up and I figured it was time to focus on finding a new girl to date – specifically a girl to have a sexual relationship with so I could finally lose my virginity. My first week at school, I met some new people but never really hit it off with any girls, except for Cassidy. Cassidy and I had the same study hall together and something was just different about her. She was about 5'5 with small tits but a great ass that always stuck out of her skirt or protruded from her jeans. She had brunette hair down to her shoulders and a tiny nose ring that I found incredibly sexy. I tried to sit close to her during those study hall sessions to find the right time to talk to her when finally she broke the ice.

"So you're the new kid in town, huh?"

"Yeah, that's me. I just moved here about two weeks ago from out of state."

She smiled and sat down close to me, pulling her chair up right next to me so that her leg was almost touching mine.

"Don't worry too much about it. In a few weeks this place will feel like home and everyone is pretty friendly. I'm Cassidy!"

I introduced myself and made some more small talk with her until the bell rang for next period. We packed our things up and she said, "You know, if you would like for me to show you around town I'm free tonight. We could go see a movie or something if you want."

Of course, my mind instantly jumped to the thought of hooking up with this sexy girl. "Sure! I would really enjoy that."

"Great! Here is my number, text me after school and we will set up some plans for tonight. It will be a lot of fun, I promise!" She winked at me as she finished talking and headed out.

I was ecstatic. Without any doing of my own, the girl I had been eye-fucking since I started school here had asked ME if I wanted to hang out with her. I could not wait for the school day to end.

When school ended, I went out to the parking lot and started up my car. I had been thinking about when and what to text her for the entire rest of the day I was so nervous. I decided on: "Hey its Sean from study hall. What time do you want to meet up tonight?"

Almost immediately, she texted back: "Sean! Let's say about 8 o'clock. You can meet me at my house." And gave me her address. I replied with, "Looking forward to it! I'll see you then."

A couple minutes later she sent another text asking if I had a curfew – it was a Friday night after all. I told her no, that my parents are pretty relaxed and let me come home whenever.

Cassidy: "Cool! I'm thinking about throwing a party because my parents are out of town. So if you can convince them to let you spend the night at a friend's house you could crash at mine after the party."

Was this really happening? Did this beautiful girl just invite me over for a party and to spend the night at her place? While her parents were gone? I was completely elated. I didn't know if she was just being nice to me because I'm the new kid or she was interested in me, but I didn't care. I was going to a party with at Cassidy's and probably a ton of other attractive girls. Could this be the night I've been waiting for?!

I got home and worked out, ate, and showered. I spent way too much time getting ready, trying to look as best as I could to interest some girl into hooking up with me. I told my parents about the party and they said that was fine, to just text them when I got there and to not leave if I would be drinking. Everything was going perfectly. I even snuck a bottle of vodka that I had hidden in my room out to the car and headed out. I sent Cassidy another text as I was leaving, telling her I was on my way with some booze. She replied: "You are awesome! I'll be waiting her for you ;)". The entire drive I was completely overanalyzing her last text – a winky face? She's waiting for me? This is it, Sean!

I stopped for condoms on the way over and made it to her house. When I pulled into her driveway, no other cars were there and I got a little worried – was she fucking with me? Is she really having a party? Did she give me a fake address to make me look like an idiot?

I called her as I got out of the car with the vodka and told her I was here. She opened the door wearing an incredible little black dress that showed off her figure – her small tits looked perky and sexy, and I could see her ass fall out of the dress when she took long strides. As I got to the door she gave me a hug and a peck on the cheek – which admittedly gave me a small hard-on already.

I told you I was excited.

She lets me inside and I ask her: "So, where is everyone else? Am I too early?"

Cassidy: "No you are right on time! Everyone will be here in a little bit, I just wanted you to come early so we could get to know each other a little better. Do you want to break into the vodka and take a few shots to get loosened up before the rest of the crew arrives?"

"Sure! Let's do it." We took a couple shots and talked for a bit. I did my best to flirt but not come off as I was trying too hard, but she was laughing at my jokes and could not stop smiling at me. After a few drinks, she said: "I've got to run up to my bedroom for something, I'll be right back okay?" As she walked passed me on the way to her room she squeezed my butt and winked at me again. And again, I got a little hard as she did it. I couldn't believe this was happening – I have to hook up with Cassidy tonight. She told me over drinks that she did not have a boyfriend or a guy she was talking to, so I was in the clear.

I took another shot and tried to compose myself while I waited for her until I heard her footsteps coming towards the kitchen. When I turned around, I couldn't believe my eyes. She had taken off her dress and was wearing sexy black fishnets that covered her whole body, no bra, and a lacy black thong. My jaw dropped and she noticed because she smiled and placed her hand on my chest.

Cassidy: "Sean, I wasn't completely honest with you... my parents are out of town for the weekend but I'm not throwing a party – well, not a big party. You and I will be the only ones having a party tonight."

Immediately I got hard and could feel my cock bursting through my jeans. She could tell I was speechless, and gave me a kiss. She grabbed the vodka and said, "Why don't I show you my bedroom?" With the bottle in one hand, she grabbed my hand with the other and led me to her room. I could not help myself from staring at her ass the entire walk there – it was as round and perfect as the pornstars I had been watching for years. I thought I was going to explode in my pants before we even got to the room.

When we got inside, she sat me down on the edge of the bed, and took a long pull from the bottle and offered it to me. I did the same, to try and calm down the situation in my pants. She took the bottle from me and set it down and stood in front of me between my legs. I was doing my best to actually make eye contact and not stare at her beautiful, supple boobs that were right in my face.

Cassidy: "So I have to ask you... have you done this before?" I did my best to come up with something smart to say – I had virtually no sexual experience besides what I had seen online and did not want to seem like a loser in front of this half naked goddess in front of me.

"Well, no actually... I'm still a virgin. I've done things before but I've never actually did it..." I said as I was praying that I did not just blow my chances with her.

Cassidy giggled and put my hands on her ass (which really almost made me explode in my pants this time). "You're so cute! Don't worry Sean, I will take care of you. Just relax and follow my lead, okay?" As she finished her sentence, she kissed me again and shoved her tongue down my throat. I wanted to wrap my arms around her and pull her on top of me so badly, but I felt her starting to kneel down all the while making out with me. She pulled away and started to take off my belt. As she was pulling my pants down, she felt the condoms in my pocket and laughed. "Came prepared, huh?" I laughed nervously and before I could say anything, she pulled down my jeans and my cock sprang out. I'm not huge by any means, but I don't have a small cock either – about 6 inches although at the moment it felt like I had a foot long dick ready to cum the second she touched it. She kissed me once more and then kissed the tip of my cock. She then took my whole cock in her mouth and deep throated me, no gag or anything. I was doing everything I could not to cum down her throat right there. She pushed me back so I could lay on the bed as she went to town blowing me.

I had never had a blowjob before but it was by far the best experience of my young life to that point. She continued to blow me – twisting her tongue and taking my full member as far as she could, while she put one hand on my balls and the other on my hand. This was amazing – its really happening. This went on for a while – with her alternating sucking my dick, my balls, and stopping every once in a while to smile at me. I couldn't believe I was lasting this long. She then kissed the tip again and looked up at me, taking some of the cum from her bottom lip onto her finger and sucking it dry. I wanted to pick her up and throw her on the bed and take her right there. She then stood up and said, "There's one more thing I need to tell you, and please don't freak out."

What could I possibly freak out about? Does she have a boyfriend who is going to kick my ass? Herpes? I didn't even care in the moment. I told her I promise and waited for the reveal – which was about to change my life.

With that, she pulled her thong to the side through her fishnets and I saw it. She had a penis. It was a little but smaller than mine but for some reason did not bother me at all. Like I said, I did not think of myself as gay, even for enjoying shemale porn, but I could not believe what I was looking at. After a short awkward silence, she said, "Is this okay? Sean, I really like you. Please don't let this be a problem – you don't even have to touch it if you don't want to. But please don't freak out and run away..."

I could tell she was extremely nervous, but without even thinking about it I reached out and placed my hand around her cock. I found it cute – it was the perfect "girly" trans cock that I had looked for when watching trans porn. She let out and nervous laugh and looked back into my eyes. Without hesitation, I got on my knees and put her cock in my mouth.

Was this really happening?

I did not feel gay, and I didn't hate it. In fact, I kind of enjoyed it. I could feel her body shiver when she entered my warm mouth and felt her cock growing as I moved my tongue around it. I sucked on it for what felt like 5 minutes and touched her balls too. She was clean shaven everywhere and I was extremely turned on. She started to pull off my shirt so I pulled off her cock to take it off. She then stood me up and took my jeans off too, and pushed me back down on the bed. I was rock hard – still amazed I hadn't cum from anything that had happened thus far. She then mounted me on the bed and shoved her tongue down my throat again. I was a little worried about tasting my own semen and dick from her but was way too into the entire situation to care. She then inched forward to put her dick back in my mouth and grabbed my hands to put on her ass again. I started squeezing her cheeks as I sucked her and closed my eyes, just taking in the entire situation. I was having oral sex with a beautiful trans girl through no effort of my own. She was moaning and gyrating her hips forward putting her cock back and forth into my mouth, all the while squeezing her tits and saying my name.

I really felt like I was in a porno.

She then told me she was going to cum and tried to pull away. With my hands still squeezing her ass cheeks, I pushed forward so she could not take her cock from my mouth and I let her blow her load. I gagged as the initial shot hit the back of my throat but most of the cum had started to leak from around my lips. She smiled at me and removed her cock, then kissed me, licking the cum from my lips and taking her own load back into her mouth. This girl was a freak and I could not be more turned on.

Cassidy then got up off the bed and pulled me upright and turned around so I was starting at her back and ass again. She bent over and said, "You better rip a whole in these fishnets and rip my thong off now because I need your cock in my tight ass." She even talked like a pornstar!

I did as my gracious host requested and she moaned as I ripped through the fishnets and panties. While still bent over, she picked up the vodka and took another drink, and I could not help myself from kissing her ass through the fishnets. She shivered and moaned again, and I went for it – I put my tongue in her asshole and started to rim her. For having almost no sexual experience I was willing to try anything and everything at this point I was so turned on. She grabbed the back of my head and shoved my face into her ass, begging me not to stop. I kept licking her boypussy and reached around to put her cock in my hand again. She was already rock hard again and I started to tease her, playing with the tip and massage her balls while tonguing her butt. She pushed backwards to lay me back on the bed and sat on my face, spreading apart her ass cheeks for me and started to blow me again. I was in heaven.

After eating her out for a bit longer, she then rolled over and said, "Okay, seriously. I need you inside of me. Please fuck me Sean." I reached for my jeans to grab and condom when she grabbed my arm and pulled me on top of her. "I'm clean, I promise. And you are going to love being inside me without one." She opened up her legs for me and I ripped her fishnets wider. Cassidy reached over to her nightstand and pulled out a bottle of lube, and told me to start slow by fingering her and she would tell me when she is warmed up for me. I wanted to fuck her right away but did not want to hurt her, so I sprayed some lube onto her asshole and started playing with it using my finger. Then two. She pulled me closer and whispered in my ear, "Faster," and kissed me again. I fingered her for another minute or so before she grabbed my hand and said, "Take me. Take me now. I need your cock Sean."

Trying to be as sexy and as cool as her, I told her to beg for it. In the sexiest voice I've ever heard, she whispered in my ear: "Please give me your big cock Sean. Please fuck me deep and hard, I need you inside me, you are driving me crazy. Fuck my ass, please!"

I told you she even talked like a pornstar.

I sprayed another few drops of lube on my cock, which was still pretty wet and cummy from her sucking on it, and placed it against her asshole. She moaned again and said, "Yes! Yes please do it please fuck me! Take me right here!" I entered her slowly, and the feeling of being inside this goddess ass cannot be put into words. She wrapped her arms around my neck and started to nibble my ear in between her panting. I started slow (because any faster and I would have came) and started to fuck her. It was amazing. We kept making out and fucking for a while until she asked to switch positions. I rolled off of her and she got off of the bed and bent herself over it.

Cassidy: "Put it back in. I need you hard and deep. Fuck me like you've always wanted to fuck."

I eased my cock back into her ass and started to pound against her. The sight of me fucking this beautiful trans girl and seeing her ass cheeks clap against my cock as I rocked back and forth is a sight I will never forget. I reached around to feel her cock again and she was still rock hard. I knew she was loving this as much as I was.

And thank god her parents weren't home – from the crashing of the bed every time I humped her to her screaming out my name, "oh my god, yes!" and "fuck me fuck me fuck me!" could have woken up the entire neighborhood. After doing doggy for a while, I pulled out, and she flipped around and told me she wanted to ride me. I laid back on the bed and she mounted me again, and started kissing me. She grabbed my cock and started to jerk mine and hers at the same time. I don't know why but I loved feeling her cock against mine.

Cassidy then put my cock back into her ass and rode me like I was a fucking bucking bronco. This girl knew what she was doing and knew exactly what she wanted. I started to fuck her as hard as I could and she continued to moan and scream for me. I told her I was going to cum and she asked if I wanted to come inside of her or in her mouth. I know I had already tasted her ass, my own semen, and dick up to this point, but something about asking her to finish me off in her mouth after this didn't seem right. But before I could even answer, I blew my load inside of her. I came more and harder than I ever have in my life and she let out another moan when I did, telling me my warm cum felt amazing inside of her butt.

She leaned down and we kissed for a while again, and when she pulled back I could see her cock was still hard and dripping precum. She then asked very coyly, "Don't say yes if you don't feel comfortable, but can I fuck you now?"

I thought to myself – I've already come this far, and just had the best hour of my life; go for it Sean. I told her that it was okay, and she could tell I was nervous. She kissed me again and promised to be gentle. I stayed on my back as she got off me and sucked the rest of the cum off of my cock. As she bent over to grab the bottle of lube, I reached to feel her ass again. She grabbed my arm and said, "Uh uh, that is mine now." With that she took her hand, collected my jizz oozing from her ass and licked it all up. I almost came again just watching her do it – this was unbelievable. She handed me to vodka and I took a drink as I felt her apply some of the lube to my virgin asshole. I had never played with my butt before and was nervous about what it would feel like to be fucked in my ass, so I took a big drink. She took the bottle from me and told me to relax, "I promise I'll go slow and you will love it."

She put some more lube onto her penis and placed it on my asshole, slowly pushing it. I started to squirm a bit and she leaned down and kissed me, with one hand guiding her cock and the other wrapped around mine. When she was about halfway in, she pulled back out slowly, and pushed back in. It hurt a bit at first, but after a few thrusts I loosened up and kind of enjoyed it. She pulled back off of me so that she was standing at the edge of the bed, still inside of me, and ripped the top half of her fishnets off, pulling out to take them off completely. She entered me again slowly and laid on top of me in missionary, never increasing the pace or going deeper while still kissing me passionately and jerking me off slowly. I pulled back to tell her I was going to come again, and she told me to hold it. After three more thrusts, I felt her pull out and come on my chest and belly. Immediately, I came too and was covered in both of our jizz. She then licked it all off of me and when she was finished, winked at me again.
After we had both finished, she laid on the bed next to me and we continued to smile and talk. Cassidy got up and led me to her bathroom where we both showered. I still couldn't keep my hands off of her ass, tits, or cock, and she couldn't let go of mine. We got out, dried each other off, and laid back in bed.

For the rest of the night, we continued to talk and give each other blowjobs, I even fingered her ass a little again because she told me that is her favorite. We finished the bottle of vodka and ended up having sex with me on top of her missionary, until I came inside of her again and we both fell asleep.

The next morning, I woke up to her bringing me a cup of coffee and wearing my shirt and a sexy pair of pink panties. I ate her ass one more time and she blew me before I told her I had to be leaving.

On the drive home, I could not stop replaying what had happened the night before in my mind over and over again. When I got home, my parents asked how the party was and I replied, "Great, I made a lot of new friends. And I think I have a girlfriend now." I checked my phone, and had a text from Cassidy – it was a picture of her wearing nothing but a pink thong, her bulge protruding, saying, "Last night was amazing. My parents don't come home for another few days... what are you doing tonight? ;) "

To be continued...

losing   trans   virginity  

Feb 18, 2018 in anal