Cousin's request changes my life with a trans girl.
Sarah and I were hanging out in the basement while our parents talked up a storm upstairs. She and I tend to see each other more often than our other cousins. You see, my mom and her mom are actually twins and have always been close, more so than with their other siblings. By default, Sarah and I are closer than we are with our other cousins. Because we're both an only child, we tend to fill in the role that a sibling usually would She's sorta like my younger sister and I tend to play the role of an older brother. She's 17 and I am 20 and in college. I have had to step in on a few occasions where she was being harassed by some asshole at school.
Anyhow, as we were hanging out, watching TV and just messing around, Sarah held my arm and asked me to press pause, claiming she had something she needed to ask me and it was super important. Not unusual, she always starts most of our conversations this way and it ends up either being something stupid or not as important as she claimed it would be. Regardless, I always play along just to appease her.
“What's up?”
“Do you remember how I told you I would be going to Prom with my friend Eileen and how there was this big secret after-party planned at Mike's house, you know, the guy in my Econ class?”
“Yeah.”
“Well, I'm not gonna be able to go and I need you to do me a big favor?”
“Why not and what favor?”
She went on to explain that apparently she had not been paying attention to her parents constant warning about her grandparent's 50th wedding anniversary. These were her grandparent's on her dad's side. It was in three weeks and they had finally put their foot down, telling her she was expected to attend. No if's, and's or but's about it. She was going. Period. End of story. Besides, she still had next year attend Prom. Sarah is a Junior and can easily attend her Senior Prom next year. On the other hand, I learned that Eileen is a Senior and this would be her last opportunity to go.
She asked if I could go in her place. She started selling me on the idea, telling me how pretty her friend was; going on and on about all the boys wanting to be with her. I got suspicious and asked if she was so pretty, why weren't all the boys at school jumping at the opportunity. She wasn't answering me, instead she pulled out her phone and showed me a pic. I stared long enough to let her know I was interested. It was a pic of them two at the mall. It must have been during summer because they were both wearing short shorts and crops tops that show off their belly buttons. They were both posing sort of sideways with both girls showing off a nice firm ass that seemed to stick out just right.
My dick seemed to also like the pic as I felt some movement down there.
“Is that really her?”
“'Yeah.”
“Does she still look like that? It's not like she gained 100 pounds since you took this picture, right?”
“In my opinion, I think she's even hotter?”
“What's the catch? Seriously, why doesn't she just go with some guy from school? You said all the guys are after her.”
Sarah had a look on her face that I knew too well. It's that look when they want to you to do as they ask without telling you the truth. She must've hesitated for a few minutes before continuing.
“We'll........I'm not asking you to hook up with her, I'm just asking you to take her to Prom and make sure she has a great time. It's not like I'm asking you to marry her.”
“Stop stalling and answer my question. You know I'm not gonna agree to anything until you answer me.”
“Ok...ok. Before I tell you, please know that I'm only asking 'cause I can't go and you're the only one I trust with her secret. It's her Senior year and I really want her to go.”
“...and?”
She looked at me for the longest time, wondering if she should really spill the beans. I suppose she was hoping I would agree simply by looking at her pic and all secrets would be kept safe. She must've forgotten who she was talking to.
“She's trans.” she finally said, almost in a whisper. Looking at me with the surprised look on my face, she continued. “She's afraid of going with anybody else from school and being discovered. Only her mother and I know her secret. She transferred to our school last year because she was being harassed at her old school.”
“She's like.....a dude?!? Wha....wha...wha...what makes you think I would want to go? Look, I don't really care what people do, they can go around in a clown's costume for all I care, but I'm straight. Straight girls is what I'm attracted to.”
She went on to explain that I was the only one she trusted, telling me that she wasn't asking me to kiss Eileen, much less marry her. It was simply to escort her to the Prom and dance a few songs with her. She didn't even expect me to slow dance with her. The original plan was for them to go to Prom as friends, but now that she couldn't go, she thought I could do her this big favor.
I sat there thinking of all the reason's on how this was a bad idea. If this ever got out, I would never hear the end of it from my friends. Secretly, I wondered what if I actually enjoyed my time with her, would that make me gay? As I sat there thinking it over, it was my cousin that made it easy for me.
“If you agree to do this for me, next time we get together, I'll suck your dick all night long until you can't cum anymore.”
She and I were what most people would describe as kissing cousins. We had been hooking up for about a year. We had done just about everything except fuck. It all started with kissing, which quickly progressed to heavy petting. Eventually her blouse and bra came off which allowed me to enjoy her cute A cups breasts. I remember the first time we did that, she was so afraid I would think they were too small. The truth was that they looked great on her tiny body. Eventually, over time, we ended up naked, orally pleasuring each other.
However, she never allowed me to fuck her, always afraid of getting pregnant and having to explain it to her parents. I enjoyed my time with her that I never pressured her to do anything she did not want to do. I tried explaining how condoms work, but even then she refused. I assumed she was probably just trying to save herself, but it's not like she was very religious. None of us were.
“Ok.” I agreed. “But, you better keep your end of the deal and not start complaining that your jaw is hurting, you do that all the time. That's not gonna be my problem.” I told her with a smile on my face.
“Oh my god, you can be such a jerk.” She exclaimed, smiling as she slapped me on the arm.
******
I went tux shopping, but Prom was only three weeks away. It was too late to rent a tux, at least a nice one. Besides, doing the math, I decided that buying a suit was probably a better choice. Who knows what other events might come up in the future and I would have a suit ready to go.
That same night after I had agreed to go with a promise from Sarah to suck me for an entire night, she called Eileen and I got to talk to her. She sounded exactly like her picture, sweet and sexy. My dick betrayed me and I actually got a chubby talking to her and imagining her in the picture Sarah had shown me.
A few day later, I texted her and asked what color was the dress she would be wearing. My idea was to buy a black suit and wear a shirt and tie the same color as her dress. I found myself texting her a few times after that for one reason or another and was actually getting to like her, as much as you can get to know someone over text. She was funny and seemed to be easy going.
*****
The day finally arrived. Nervously, I got out of my car and walked up to her apartment. Eileen lived only with her mom. Her father had left when she was only 2 years old and they never heard from him after that day. I lightly knocked on the door and her mother answered. She seemed happy to see me and quickly moved to the side as she invited me in.
“I hope you don't mind waiting. She's almost done. You know how us girls can be when we're getting ready.” I assured her I was in no hurry. Tonight was all about Eileen. We made small talk about our plans. I had originally agreed on taking her to the Prom and bringing her back home, but after texting back and forth, curiosity had gotten the better of me and I actually offered to take her out to dinner before heading to the big event. She hesitated at first before accepting my invitation to dinner.
Holy fuck! My bottom jaw hit the floor when I first saw her walk into the living room. She was fucking stunning! She looked ten times better than what I was expecting. Long blond wavy hair down to the middle of her back with a gorgeous face and perfect make up. Her red pouty lips confirmed that I had made the right decision on agreeing to take her out. For a moment, I totally forgot she was trans and my dick was waking up.
She was wearing a strapless long green dress with a slit down the side showing off her long smooth leg. She was wearing open-toed high heels that made her one exposed leg look very nice. Plus, the color of her dress was a perfect contrast to her blond hair and light skin. The dress fit tight on her, only helping to accentuate her B cup tits and scrumptious ass. Her nice, round ass cheeks made me want to reach and grab a handful of ass. She looked fucking hot! In a very classy way.
It took me a minute before realizing I was staring. It was her mother that brought me out of my stupor when she asked if I didn't mind taking a few pictures before we left. She wanted to make sure we left on time so we wouldn't be late for our reservations for dinner. We took a few pictures in different poses, the last one was where we were holding hands and facing each other. Sorta as if we were getting married. We stood there looking into each others eyes as I took in her beauty. I'm not sure what kept me from kissing her.
Holding on to her hand, I led her out the door and held onto her down the walkway and did not let go until she sat down while I held the car door open for her. I warned myself not to get too excited, reminding myself that she was trans, not exactly my type for one simple reason.
It seemed like everyone at the restaurant was looking at us, but I'm sure it was her they were staring at. For the moment, I felt a bit of pride being seen with such a beautiful lady, once again forgetting about her secret. Dinner was great. We talked and laughed. I was having a genuinely great time. In fact, there were a few times she caught me staring at her tits and instead of making a big deal, she just giggled.
We wrapped up dinner, I paid the tab and we made our way to the venue. In this case it was at the Hilton, the nicest hotel in town. When we parked, I told her that I was here for her and tonight was all about her. We could leave at any time or we could stay as long as she wanted, all she had to do was tell me. I asked her to stay in the car and wait for me to open her door.
It seemed like all eyes were on her the moment we walked in. Eileen is slim and normally stands at 5' 7”,but tonight she was close to 5' 10” in her heels and compared to all the other girls, she looked like a model. The strapless dress showed off her smooth bare shoulders, her arms and manicured fingers with matching polish on her fingers and toes. We stopped for a moment at the entrance and I turned to her asking if she was ready. She smiled and nodded, confirming she was ready. Our first stop was to get in line and take our picture.
A lot of the girls were coming up to compliment her, telling her over and over how beautiful she looked and how great that color looked on her. I even heard some of the girls asking who her date was and telling her how cute I was. It was at the point that I decided to throw caution to wind and try to make this evening extra special for her.
She was still surrounded by several girls when our turn to take our picture came up, so I stepped over to get her. I reached out and held her hand.
“Babe, we're up.” I said as I kissed her cheek. “Excuse us for a moment, ladies.” Both she and the girls stared at me for a second before she followed me. As we stepped away, I could hear the girls excitedly commenting on how sweet I was with her, wishing their stupid boyfriends would treat them like that.
Standing there posing for our picture, Eileen thanked me, telling me nobody had ever treated her that way. I reiterated that tonight was all about her. I was her escort and I had promised Sarah that I would make her feel special. She looked at me and then leaned in and kissed me on my cheek. Her plump red lips felt so soft that it woke up my dick.
A lot changed for me that night. The girls she had been talking to had saved us a couple of seats at their table. They yelled out to Eileen when we were done taking our picture and we walked over to join them. The rest of the night went by flawlessly. Eileen spent time talking to the girls, dancing with me and just really having a great time.
At one point, we were on the dance floor and the DJ decided to slow things down a bit. Sarah had told me I wasn't expected to slow dance with her and I assumed she and Eileen had talked about it because when the song started, she turned as if getting ready to walk back to our seats. That was also when I pulled her back to me and wrapped my arms around her. She looked up at me a bit confused.
“Are you sure?” she asked, with a weak smile, cautiously excited.
“Yeah.” I said, before leaning down and kissing her on the same lips that had been driving me crazy since the first time she walked into the living room. At some point from when I first picked her up to this moment, an attraction towards her had developed. I stopped caring about her secret. All I knew was the gorgeous lady in my arms really turned me on. We broke away for a moment and slow danced for awhile, before we went back to kissing. It started off slow, kissing close-mouthed before she parted her lips and my tongue went exploring into her mouth. Things got a little too intense between us that one of the chaperon's had to come tap us on the shoulder, reminding us it was still a school event and we were expected to behave appropriately.
After the song was over, we made our way back to our seats as changed people. I kept an arm around her the rest of the night, enjoying her soft bare shoulders as I ran my hand up and down her smooth arm. It felt like I was in a daze the rest of the night. I had no regrets kissing her, but I was wondering what would happen after tonight. It's not like I'm into guys, for fuck's sake. For tonight, I decided to enjoy her company.
After the lights came on, we grabbed out stuff and made our way to my car. I walked her to the passenger side and opened the door for her. Before she could sit down I pulled her back to me and hugged her tight as we started making out once again. I wasn't sure how many other people she had kissed, but she was a great kisser and her lips were driving me crazy. I even bit her lips hard enough to get a reaction from her. I apologized, telling her it was her fault for having such beautiful lips.
We finally separated and made our way to Mike's house for the after-party. Why his parents allowed a bunch of high school kids to take over their home, I'll never know. But, then again, it wasn't my problem. The party seemed to be extension of the Prom. All of the same people that I saw just a few minutes ago were now at this party. The only difference was that a lot of them were getting drunk and acting like stupid high school kids do – loud and obnoxious, telling each other how much they had been drinking and how drunk they felt.
If we weren't kissing, Eileen and I were laughing at the drunk kids acting silly. We were actually having a great time. I did notice some kids go upstairs and I'm sure they weren't up there using the upstairs bathroom. A few of girls came back down with disheveled hair. I thought about it for a moment, but I didn't want to pressure Eileen. I wanted to keep it PG13 and make sure she had fond memories of her Prom night.
At about 3 am, she turned to me and asked that I take her home. She'd had tons of fun, but was starting to feel tired and did not want her mom to worry about her. Because of her secret, she tended to worry about her more than most other mom's. I suggested she text her, letting her know we were on our way home. We said good-bye to a few sober people around us before making our way to the car. Same as before, I brought her into my arms we kissed like lovers. By this time, we were very comfortable kissing each other; it actually felt like we had been kissing longer than a few hours. I knew she could feel my hard cock pressed up against her, but I really didn't care.
On the way home, I pull over and parked a few blocks from her apartment building. I wanted to thank her for a great night. She too thanked me, telling me that if I had not agreed to take her, she probably wouldn't have gone and she was glad she went. We stared at each other for a moment before we went back to kissing. The slit on the side of her dress exposed her left leg and I just couldn't resist. As we kissed I started her caressing her leg, which only got my cock harder than what it already was.
Same as before, it got hot and heavy between us, so much so that I did not notice when she started grabbing my cock. Before I realized what was happening, she has undone my pants and my hard cock was out and proudly standing at attention.
“I've never done this before, but I really want to suck your cock. May I?” she whispered while looking into my eyes. I was in shock and could only nod my head. She bent down and took my cock into her warm mouth. It felt so fucking good. She started off slow, but soon she was bobbing her head faster and faster that I started questioning if it was really her first time.
She kept at it for close to five minutes and all I could do was lean my seat back and enjoy the blowjob. My moaning started getting louder and louder and I started warning her, letting her know I was about to cum. I grabbed her shoulders, trying to pull her away, but she pushed my hands away and kept sucking my cock as if her life depended on it.
“Babe, babe!” I had been calling her that all night that it just came out. “I'm gonna fucking cum!” I yelled as her perfectly plump lips continued sliding up and down my cock.
Suddenly, it was too late. My nuts tightened up and cum shot out spurt after spurt into her exquisitely warm mouth and down her throat. I had never felt like I did at that moment. Several girls, including Sarah, had given me some really good blowjobs, but never anything like Eileen did that night. I came hard and she coughed, but never took my cock out of her mouth, managing to swallow most of it.
*****
I woke up pretty late the next morning. I had gotten home pretty late the night before due to the after-party and the time Eileen and I spent together before finally taking her home. I started thinking about the events from last night and I was more confused than anything else. Had I really kissed a guy? Did I really let him give me a blowjob? Did that make me gay? I really didn't know the answer to these questions, but I did know it wasn't something I was going to call any of my friends for advide on helping me figure it out.
What I did know was that for some fucking reason, I couldn't stop smiling. I really had a great time and I wanted to see her again. No fucking clue why, I just knew I had to. She turned me on.
Without thinking, I grabbed my phone and started texting her.
Me;
Her:
Me:
Her:
Me:
She waited for close to five minutes before answering. It was killing me! I thought maybe I had pushed too much too fast.
Her:
Me:
Her:
What the fuck did I just do? I really wanted to see her, but was it a good idea? I mean, after last night, she might expect us to kiss and hold hands and I wasn't sure about that. Fuck, I was totally and completely baffled.
Even when I started getting ready to go pick her up, I changed my clothes several times. Shirt or t-shirt? Jeans or khakis? 'Fuck, it's not like it's date, right?!? It's just two people hanging out and enjoying each others company. I kept telling myself that; totally disregarding the fact that one of those friends sucked the other friend's cock AND swallowed most of his cum the night before.
I couldn't wait any longer. I was ready by 5pm, but waited until 6pm to text her.