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; [hey, I had a good time last night. I hope you did too.]
Her: [I did. Thank you so much for a lovely evening. It was so much better than what I ever expected.]
Me: [I hope I didnt make you do anything you didnt wanna do]
Her: [You didnt. Youre sweet for being concerned, but I enjoyed everything we did]
Me: [hey, would you like to hang out later today, maybe go get something to eat]
She waited for close to five minutes before answering. It was killing me! I thought maybe I had pushed too much too fast.
Her: [sounds like fun. Sorry for the delay, my phone went dead and I couldnt find my charger]
Me: [No worries. 7 sound good]
Her: [cant wait]
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.
Me: [hey, I'm kinda hungry. Do you mind if I come by a little earlier, like 6?]
Her: [till getting ready. Can we make it at 6:30pm?]
I was parked just around the corner from her place, but she didn't need to know that. What the fuck am I doing, I sat in the car second and triple guessing myself, wondering if this was a good idea. This could only end in disaster and then Sarah would really be pissed off at me for leading her on. Eileen would tell Sarah how I invited her out and then never showed up. I decided I would take her out to dinner and then tomorrow I could tell her that maybe it was best if we just stayed friends.
Eileen answered the door and I have no clue where all those thought went. We were having an unusually warm day and she was dressed for it. She looked fucking cute, as in the girl next door that you want to take into your arms and kiss her and never stop kissing her. She had her hair up in a pony tail wearing some really cute glasses, along with a white tube top with a white blouse over it. Tight khaki shorts and a pair of cute sandals completed her outfit. Her smooth legs looked great!
“Hi.” she greeted me with the cute voice that matched her look.
“Hi.” I answered. “You, you look nice. I didn't know you wore glasses.”
“Normally I use my contacts, but we were up late last night and my eyes are feeling a little dried up. Do they look funny on me?”
“Oh, no. Not at all, I was just surprised. In fact, they make you look very smart.”
“Thank you.” she said as we both laughed.
Same as the night before, I grabbed her hand and walked her to the car, again opening the door for her. Before sitting down, she turned to my gave me a quick peck on the lips. As you would've guessed, my cock started getting hard. I was 20 at the time and very much a virile young man. After going back and forth on where to eat, we settled on pizza. I wasn't in the mood for regular old pizza, I wanted to take her to an Italian restaurant and have some real pizza.
We made our way over to Giovanni's, a place my parents had been going to since before I was born. The food is great and the staff is always nice. We sat down to eat and I told her she could pick out whatever kind of pizza she wanted, so long as there were no anchovies. She laughed, telling me she loved anchovies. She saw the look on my face before laughing, letting me know she too hated anchovies. I loved that she felt comfortable enough to tease me.
I was afraid it would be kind of awkward now that we were actually alone. Her friends were not around, there were no drunk kids to make fun off, and we didn't have our tongues down each other's throats making out. Surprisingly, it went better than I expected.
Of course, we talked about the night before and she thanked me, telling me how special she felt when I first went to get her and kissed her on the cheek. She told me that later on that night a few of her friends told her how lucky she was to be with such a gentleman. We talked about her plans after high school, with her telling me that she was planning on attending fashion school. I told her if she continued with the same fashion sense as last night, I'm sure she was going to kill it. She gave me the biggest smile I had seen on her before she leaned over and kissed me. It was obviously not a make out kiss, but also not just a quick peck. It was the kind of kiss that a girl gives a guy she really likes.
“Oh, I'm sorry. Did I do something wrong. After last night, I thought......” she trailed off and did not finish her sentence. I had a confused look on my face, I'm sure. I loved the kiss and that was the problem. I liked it too much.
“No, you did nothing wrong. It's just that.......well, never mind. Are you ready to go?”
“Yes.”
“Do you think your mom would like the left over pizza.”
“Actually, she's not home. She won't be back until tomorrow. Since tomorrow's a holiday, she went to visit my aunt Penny. I was gonna go with her until I got your text.”
“I'm sorry, I didn't mean to.....” she put a finger up to my lips to shut me up.
“I am where I want to be.”
We drove back to her place and she obviously noticed on how quiet I was on the way over. Fuck! This was all new to me. Up until a minute before I picked her up last night, I knew who I was and what I liked and now my pecker is getting excited over a trans girl? Seriously?!? What the FUCK!!!!
“Is everything okay? You've been pretty quiet ever since we left the restaurant.”
“Yeah. I just have a lot on my mind.”
“Jake, I know how you might be feeling and I'll understand if you don't want to see my anymore. I won't even tell Sarah anything tonight, I'll just tell her that you were a complete gentleman and brought me home safely from the Prom.”
“I'd like to walk you to your door?” I told her after thinking about she had just told me.
“I'd like that.” There it was again, her smile. The smile that made me happy every time I saw her.
“Wait here”
I walked around the car and opened her door before I reached out, offering her my hand as she got out. Holding onto her, we walked up the walkway to her front door. There's a little step in front of the door that got her almost to my height. We were practically seeing eye to eye. All I could see was this beautiful girl that was so sweet. I could only imagine what kind of girlfriend she would be if only she wasn't.......
I opened my mouth to say something, but instead my arms went around her slim waist. I pulled her to me and our lips met. We stood there in front of her door kissing for awhile. Her arms went around my neck and I pulled her in tighter against me. I'm sure she could feel my hard cock pressing up against her crotch, but I wasn't exactly thinking straight at the moment. I was too consumed enjoying her succulent lips.
When I felt her pulling me harder into her arms, I dropped my hands down a few inches and grabbed her ass for the first time. Fuck, it felt better than how it looked and believe me, it looked fucking awesome! I couldn't help myself. As we continued kissing, I grabbed and squeeze her ass. It was a good thing it was now dark as she had left the porch light off when I first picked her up.
“Would you like to come in? I don't want the neighbors telling my mom about what they saw.”
“Ok” I said. The entire conversation took place without us ever separating our lips. Unfortunately, we had to stop for a moment so she could search for the keys in her purse. She opened the door and I stepped in. She turned around and locked the door before grabbing my hand and pulling me behind her as we made our way to her room. Once more, I pulled her to me and we continued where we had left off, only this time we were on her bed with her on her back and me between her legs.
My lips went from hers to her neck. I could hear her breathing heavily, enjoying what I was doing to her as her hands went under my shirt as she started running her hands up down my back. One of my bigger turn-on's is when a girl drags her nails up and down my back. That is exactly what she was doing. I continued kissing my way down, now kissing her chest, just above the tube top, I expected her to stop me, but she just kept moaning and breathing heavily.
Fuck it! I decided to just go for it. If she stopped me, I wouldn't insist. I reached up and my hand first landed on her tummy before I started sliding it up, under the tube top. She never stopped me. It was the opposite of what I was expecting. She pulled down her tube top and placed my hand directly one of her nice, firm tits. I went back to kissing her lips as I grabbed and squeezed her tit,s enjoying its firmness and hard nipple.
We went on like that for awhile as we dry humped with her legs wrapped around my waist. I was grinding my cock against her crotch and sucking on her neck. We were both so revved up and horny for each other that we wouldn't have noticed if her mom walked at that moment. Thankfully, she never did.
“Please suck on my tits, baby. Oh fuck, please just suck on them.” She didn't need to tell me twice. I hastily took one of her tits into my mouth as I flicked her hard nipple with my tongue. To be honest, I couldn't tell the difference between her breast and Sarah's or any other breasts I'd had the pleasure of enjoying. Her breasts were soft, but firm and her nipples were just as nice, if not better, than others I had sucked on.
I continued sucking her tits, alternating between the two, having a hard deciding which one was my favorite.
“Harder, baby! Suck on them harder!” she screamed. I was going as hard as I could, taking most of her tits in my mouth. There were a couple of times I tried reaching down between us, but she was quick to move my hand away. I suppose I could understand why. There toward the end she begged me to bite her, telling me she needed me to pinch one nipple while I bit the other. That was when she went quiet and her body stiffened, it was obvious she was cumming.
I soon started smelling the familiar smell of cum. You know, kinda like ammonia. You would've thought that would have been a turn off, knowing that she had just spilled cum from her penis, but it actually had the opposite effect. It got me harder knowing I had given her sexual pleasure. I wasn't questioning much any longer. I was simply going with the flow and doing what felt good.
“Stop....stop....stop!” she panted. I did as she asked and pulled away, detaching my mouth from her tits. She got off the bed and removed both her blouse and the tube top that was around her waist, showing me her tits in all their glory. My god, it only reinforced what I already knew. What anyone who met her already knew. She is fucking gorgeous! Her perky tits are a solid B and they look great on her. I would later learn they were all natural, thanks to the hormones she was taking. They were not implants. They were definitely hers.
She suddenly had the look of someone who knew exactly what she needed. She looked at me standing there topless with her hands on her hips while still wearing her khaki shorts.
“Take off your pants. I really need to suck your cock.” With out any argument. I pulled down my pants and briefs before kicking them to the side. “Your shirt, too.” I did as she commanded. She asked me to get back on the bed and lay on my back. She went around and came up from the foot of the bed. From the beginning, I knew this was not going to be a ordinary blow job. I laid my head back and enjoyed her efforts.
She started by kissing the inside of my thighs, teasing me as her mouth got closer and closer to my cock, with her slowly stroking my cock. Her mouth would get close to my balls before she would pull away. Her mom was not due to come back until the next day, so she knew there was no hurry. There is nothing sexier nor crazier than a woman slowly stroking you as she softly starts licking your balls, gently taking one then the other into her mouth. That was exactly what she started doing.
Looking up at me with her beautiful blue eyes, she started licking my cock as if it was her favorite popsicle. She slid her tongue on my cock from the base slowly up to the head. She would kiss my head, before starting at the base once again, sliding her tongue from the base up to the head. She did this several times, slowly, with a smile on her face and her piercing blue eyes staring back at me. Was she really telling me the truth last night, I wondered. Had she simply seen a tutorial on how to give mind blowing bj's on YouTube?!?
After several minutes of her sweet licking, she decided to get down to work. She opened her mouth wide and took my cock into her mouth as she wrapped her lipstightly around my cock. The same dick sucking lips that had been driving me crazy since the day before when I first met her were now around my cock. She also started humming as she cradled my balls. Eileen was genuinely enjoying herself as she sucked my cock. The greatest pleasure any woman can give her man is to show him how much she really loves him and how much she loves his cock.
After her sexy licking and hard sucking, it wasn't going to take long before I came. One thing I had learned about Eileen the night before was that she loved swallowing my cum - another thing women can do for their men.
“Fuck, baby! You're making me cum. I'm gonna cum, I'm gonna cum.” As a courtesy, I kept warning her. I knew she wouldn't pull away, but I also didn't want to catch her off guard. She doubled her efforts and suddenly my nuts tightened up and exploded as I came, shooting my cum non-stop into her welcoming mouth. I must've shot a couple of spurts into her mouth before she pulled back and aimed my cock at her tits as they got bathed with my cum. I was definitely not expecting that.
She looked at me and smiled before opening wide to show me my white cream in her mouth before swallowing it. How had she learned to be so fucking nasty? Either she was lying about this being her first time or she was watching a lot of porn. I really didn't care which was it, all I knew was that I wanted to do this again....and soon.
I was Confused, with a capital C after that evening. I kept seeing her after that night. It seemed like I couldn't get enough of her. Whether I was at work or at school, she was constantly on my mind. The one thing I did that made me question things was that I started watching gay and trans porn, something I had never done before. Again, what the fuck is going on, I asked myself. That just wasn't me.
*****
The following weekend Eileen had some family visiting for the weekend and was unavailable. The lucky coincidence was that my parents were out of town. I called Sarah specifically to collect on my bet. I needed to remind myself that I still liked pussy, not that I was going to get any, but you know what I mean.
My cousin can be a fucking tease and that night she decided to come over wearing the tightest blouse she owned with no bra. Her nipples were hard as fuck, making themselves known as they nicely pressed against her blouse. Along with her tight blouse she was wearing a pair of boy shorts. She drives me crazy when she dresses like a fucking slut!
The moment she walked in I took her into my arms and kissed her as I grabbed her ass. My cousin probably has the second nicest ass at her school, after Eileen. We made our way to my room, undressing each other along the way, with our clothes forming a trail on the floor behind us. When we finally closed my door behind us, we were both completely naked.
I sat on the edge of the bed and grabbed a pillow, throwing it on the floor in front of me. She looked at me with a smile and shaking her head before dropping to her knees. We both knew she was there so I could collect my reward for the big favor I had done for her.
Sarah reached out and grabbed my hard cock before she started jacking my off while licking the head of my cock.
“Does this feel good, cuz? You really enjoy it when your baby cousin takes your big, hard cock into her warm mouth, don't you?”
“Fuck yeah.” was all I could say as I enjoyed the warmth of her mouth on my cock. As we continued, I was finding it harder and harder to not compare her to Eileen. I laid back and started imagining it was Eileen who was sucking my off. That made cum a lot sooner than what I normally did.
“Fuck, cuz, that was a lot faster than normal. It does make sense, we haven't had a chance to get together for awhile.” she exclaimed after swallowing.
“Yeah, I guess so.” I responded, just playing along without giving away my secret.
She came up and snuggled up next to me as we started kissing. I've never swallowed cum, but I kinda like the taste of it when she kisses me after swallowing my cum. It reminds of what she just did for me.
While we laid there in bed, she told me that she had found out from friends that went to the Prom that Eileen and I were making out. I played it down, telling her about the incident where I had kissed her on the cheek when I went to get her for our picture. I explained I was simply trying to make her night special, claiming her friends were obviously exaggerating.
She seemed to have bought it and thanked me for taking Eileen to the Prom and making it extra special with the kiss and taking her to dinner. At that moment, she reached out and grabbed my dick. I had not realized I was hard again.
“A promise is a promise.” she said as she lowered her head and went back to work. In the end, she ended up swallowing four loads that night. Although not part of the deal, I ended up eating her out twice in between blow jobs. I needed to prove to myself that I still liked pussy.
*****
After a couple of months of secretly dating Eileen, I knew what I wanted. I suppose I wanted it from the start, I just didn't realize it. It took me time to get the courage to do it. In fact, it was her that had to ask for it. I just didn't know how to go about it.
During the past couple of months, we had done a lot of the same and I was loving it. We would end up in bed, either at her place or mine, making out before her blouse would end up somewhere on the floor and I would end up completely naked. I would enjoy her tits and she would suck me until I came in her mouth. She was becoming a cum whore and I loved it.
On this particular night, we were in her room, enjoying our alone time. Her mother was out of town with some work friends on a trip to casino we have that's about two hours away. They usually take a charter bus and spend the night at the hotel. It's sort of a mini vacation for them. They get to gamble, sit by the pool and eat great food the entire weekend. I was hoping Eileen and I would soon take a trip there ourselves as a couple.
She was laying on her back and I was on her, laying between her legs. She had wrapped her arms around my neck and her her legs around my waist. As usual, things were getting pretty hot between us when she suddenly pulled away from me. She placed her hands on my shoulders and slightly pushed me away.
“Baby?” she said very sweetly, almost in a whisper.
“What's wrong?”
“Nothing.” she said as she tried to catch her breath. But, I knew something was up. There was a look on her face that told me she wasn't exactly being truthful.
“What's wrong?” I insisted.
“I...I....I want you to make love to me.” she said before closing her eyes, embarrassed and afraid of how I would respond.
“Seriously?” I asked, not bothering to hide the excitement in my voice. She just nodded as she smiled back at me. She asked me to get up, telling me she first needed to use the bathroom. We had just started, so she was still wearing her blouse and the skirt she had worn to dinner and I still had my pants on. I had thrown my shirt in some corner when we first entered her room. I decided to take off my pants and wait for her wearing only my briefs. Before leaving, she reached into her nightstand and gave me some lube. The bottle was new, still unopened.
After a few minutes, she came out looking like a Victoria's Secret model and my cock immediately stood up, something had obviously peeked his interest. Green was definitely her color. Her hair was loose and she was wearing a satin green camisole that came down to just above her panties. A pair of sexy panties with lace along the edges that only covered half her ass. She stood in the middle of her room and turned around, stopping half way, allowing me to check out her ass before completing her turn.
“Holy fuck, babe! You look......” I hesitated for a moment, unable to find just the right word. “You look like a fucking dream come true. You look like......a sexy angel.” She really did. I'm not sure if angels are allowed to fuck, but this angel had dressed for the part. Everything about her was screaming sexiness! Her smile, her hard nipples pressing up against her camisole, her long smooth legs! Everything!!
I sat on the edge of the bed and she came to stand in front of me, standing between my opened legs.
“Do you really like it?”
“You look so fucking sexy.” I said before kissing her. I wish I could say that I slowed down a bit to enjoy her in the outfit, but I was too fucking aroused. We kissed passionately as I alternated between running my hands up her back, under her top followed by grabbing her satin covered ass. I loved having her arms around my neck as I ran my hand all over her.
Eventually, I pulled her top up, uncovering her delicious tits before I tried taking one of her entire tits in my mouth, flicking my tongue on her hard nipple. I tried to take off her panties, but she quickly reached down to stop me. I wasn't sure what that was about, I could only assume she was feeling nervous. My hands went back to caressing her side as I continued sucking her tits as she moaned. We were both feeling so fucking aroused.
After a while, she got on the bed on her back and I got between her legs. She laid there topless with her blond hair splayed out with her firms tits exposed, waiting to be licked. She was still wearing her green panties that looked great on her. We went back to kissing and making out, moving my lips between her lips and her neck as she reached between us to grab my cock. With the excitement of what we were about to do, it was as hard as baseball bat ready to serve its purpose. We laid there for only a short moment before I hear the words I had been dying to hear.
“Make love to me.” she turned around and got on all fours. With the situation I found myself in and the gay and trans porn I had recently seen, I knew that we could've also made love missionary style. I would've preferred to look into her eyes the fist time, but I wasn't about to argue. I grabbed the lube and applied plenty of it on my cock before applying some to her ass. I could hear her moaning as I slid my had up and down her ass. She was enjoying the special attention I was giving her sweet little asshole. The same hole that I would soon be stretching as I penetrated her with my hard cock.
I started her off by first inserting a finger. I'm not sure who was more excited between the two of us. She was only the second virgin I would be making love to and only the second person I would be fucking in the ass. My girlfriend in my freshman year of college was actually a senior that knew what she liked and wanted. She was my first for anal sex. I learned from her not to just stick it in.
In time, I had three fingers in Eileen's ass and she had her face buried in the pillow. I'm sure if she had not done that, the entire building would've heard her moaning and screaming. It definitely got me going. I was ready to go. Without knowing, I had been wanting this for a very long time.
I positioned myself behind her. Grabbing my cock, I pressed it up against her little brown starfish and started rubbing up and down. Her moaning told me it was having an effect on her. She started pushing her ass back, as if trying to get me to penetrate her.
“Ok, babe. Just try to relax. I'm gonna go slow, but it's gonna hurt a bit,. Don't worry, sweetie, I'll stop if you ask me to.”
“Ok.” I could hear the apprehension in her voice and the suspense was getting to her. I continued rubbing my cock on her anus, getting her aroused and that's exactly what I wanted.
“Mmmm....mmmm. Please, Jake. Just do it already. I can't take it anymore. Please, baby.” she begged, almost in a whining tone.
I lined up my hard cock to it's target and slowly started pushing in.
“OH FUCK!” she yelled. “That fucking hurts!”
“Do you want me to pull out.”
“NO! Don't you fucking dare pull out!” Her response caught me completely by surprise. I had never heard her raise her voice, much less cuss. However, she had managed to do both in one sentence. I did as I was told and continued penetrating her tight little ass. It was easily the tightest hole I had ever fucked. I kept pushing forward and before I knew it, I felt her ass cheeks pressed up against me. My cock was completely in her, every last inch. Holy shit!
I held myself there for a moment, taking in the moment and enjoying the sensation of her sphincter tightly grasping my cock. Fuck, she felt good!
“Jake, can you just wait there for a moment? It's starting to feel better. I just need a little time to get used to it.”
“Of course, babe. Just tell me when you're ready.”
“Ok.” We stayed quiet for a moment while connected as one. It felt like forever as I waited, but it was probably no more than a few minutes before I felt her starting to rock back and forth as she fucked herself on my cock. I grabbed on tight to her hips and helped her, pulling back to me as I pushed my hips forward, shoving my cock in and out of her ass. We may have started slow, but we were soon full on fucking. It felt so natural being with her, as if we had been doing it for the longest time.
She continued moaning and she was getting louder and louder. I had to push her head down into the pillow. As much as I love hearing a woman scream during sex, I also didn't want her neighbors hearing us. I leaned down a bit and managed to grab her tits. This only seemed to arouse her even more, if that was even possible. We had developed a rhythm by this time with her pushing back while I pushed forward before both us pulling away before reconnecting, over and over.
I was alternating between grabbing her tits with one hand and then the other before getting up and grabbing her hips to pound hard into her as humanely possible. It was the best fucking I had ever experienced and it happened to be with a trans girl, my trans girl.
We must've been fucking hard for what seemed like forever, but was probably closer to fifteen minutes when I felt her ass squeezing my cock tighter then ever.
“Oh, fuck! I'M CUMMING, I'M CUMMMING, BABY” she screamed out at she started shooting out cum onto the bed below her. The smell, that I had developed a love for, triggered me as well and I started filling her ass up with my cum as I started shooting spurt after spurt as she lost her virginity. The euphoria you feel when cumming had never felt so intense for me.
After cumming in her for the third time that night, we laid in bed completely tired. We were laying on our sides with her back to me and my dick nicely wedged between her ass cheeks as I caressed her tits. We started talking and I asked her not to share anything we had done with Sarah. I explained that I was not ashamed of being with her or what we did, I just needed time to process the whole situation.
“I understand.” she said. She wasn't upset, at all. She completely understood the situation. I had never asked her not to say anything to Sarah before, but I assumed she never did because Sarah would've called me the second she found out.
*****
Thus, our relationship took another turn. It had developed into a full-on sexual relationship. It wasn't always possible to go to her place or mine. Often times, both our parents were home. Her mom knew something was going on between us, but I'm not sure how much Eileen had shared with her. I never really asked her. On one occasion when I went to pick her up on a Friday night, Eileen's mom answered the door and invited me in while Eileen finished getting ready.
“Hi Jake. Please come in.” she said when she greeted me.
“Hi.” I responded.
Our conversation was a bit generic, asking me where we were planning on going, asking me how was work and school. I answered her questions, getting a bit uncomfortable. I wasn't getting a good vibe from her until she finally said what was on her mind.
“Jake, I know that you aware of my daughter's secret. What you and her do, is between the two of you. All I ask is that I you not play with her nor hurt her.” I assured her I was not playing with her and that I really liked Eileen, regardless of her secret.
*****
The night that solidified everything for me and my relationship with Eileen, was a night we were hanging out at my place. We were enjoying each other in my room; we had just finished fucking and I had gone to the kitchen naked to grab us a bottle of water. My parents were gone for the weekend and we had the house to ourselves.
When I walked back into my room, Eileen was looking so fucking sexy. She was laying on her tummy with her back curved and her succulent ass sticking out in the air. She looked at me with devilish smile on her face and her blond hair splayed out behind her. She was teasing me. She knew how I loved when she positioned herself that way. Fuck! I just wanted to fuck her at the moment. No foreplay, no kissing, no nothing. Just lube up my cock and fuck her hard. That is exactly what I did.
“Stay that way, babe. I'm gonna fuck you - ready or not.” she giggled, another thing about her that drives me crazy. She knows how much she turns me on. She stuck her hand out and I grabbed the lube from her as I generously applied some to her ass and my hard dick. I can't really explain how crazy aroused I felt at that moment. We had obviously had sex just a few minutes before, but there was something about the way she looked and the excitement I was feeling.
I climbed on the bed behind her and lined up my cock with her cute little hole. The same hole that had brought me so much pleasure. I grabbed my cock with one hand and held on to her hip with the other as I pushed forward until my cock entered your sweet little asshole. It always feels so fucking good when it first goes in and that time was no exception.
Grabbing both her hips, I shoved my cock all the way in, not stopping until I felt her ass pressed against me, preventing me from going in any further. Her moaning showed me she too was just as horny as I was.
“Mmmmmmmmmm! Fuck, that feels so good, baby! I fuckin' love your big, hard cock in meeeee!!”
“I'm glad you love it, my little slut. Now, hold on!” I said to her before I started pounding her hard. There was no slowing me down. This was really not for her pleasure. In fact, I really wasn't even focused on making her cum – this was for me. There was an echo in the room as our bodies started slapping against each other, with my balls hitting hers every time I forcefully pushed in. I was on a mission to tear her ass up as I pumped in and out, over and over.
I don't think I had ever fucked anybody as hard as I was fucking her at that moment. Her moaning only kept getting louder and louder which only confirmed that she was loving it just as much as I was, if not more.
We must have been at it for a long while when a familiar feeling started developing as my nuts started to tingle. I knew I was close. Staying inside her, I leaned us over so that we were now laying on our side, in a spooning position. I continued fucking her hard as I reach over with my right hand and grabbed her tits, squeezing them hard as her nipples burned a hole in the palm of my hand.
“Jack off, baby. I want you to cum for me.” I yelled at her. I was too fuckin' riled up. I wasn't asking her, I was telling her. “Grab your fucking dick and jack off for me!! Cum for me!” She hesitated for a second before she reached down between her legs and started doing as I had told her.
Up to that moment, we had not acknowledged her cock. It was something that was there, but we did not talk about it. She would never take off her panties until she was in position on all fours.. Whenever we fucked, it was always doggy style, as if she was trying to hide it.
I was going wild fucking her from behind as she jacked off. I held off for as long as I could before I finally exploded, filling her ass up with my hot cum. Spurt after spurt kept shooting out and filling her up. It felt like I had been saving it for over a month.
“I'M CUMMING, BABY, I'M CUMMING!” I exclaimed. “CUM WITH ME YOU FUCKING LITTLE SLUT!!”
“AAAHHHHHHH!! I'M CUMMING!!” she screamed as she too shot out spurt after spurt of cum, some of it landing on her on tummy, but most of it on the bed. That was moment I knew I was hooked. There was no more doubting myself. She was mine and more importantly, I was hers.
I know she's not a lady in the traditional sense, but she's MY lady and I intend to treat her that way. She deserves to be spoiled and I want to be the man that does that for her. She makes me happy and fuck, she turns me on like no one else. I can't wait to see what the future holds for us.