My Bet to Fuck a Straight Guy

My name is Vanessa, a 28-year-old transsexual girl living in San Francisco. I am 5'7" with long black hair and decent size breasts which I got two years ago. I am quite passable as a typical sexy Asian girl and people are shocked when they find out that I have a penis between my legs.

I am attracted to both guys and girls but I lean more towards gay or bi guys. This is the story of a bet that I made with my friend Brad. He bet me $100 to see if I could seduce a straight guy and have sex with him and I accept it. I had one week to make it happen.

I'm not a slut by any means, but I enjoy sleeping with a new person from time to time. I am a bit more comfortable picking up girls. However when it comes to guys, I get shy and I have to wait for them to approach me. So, this was not going to be an easy bet for me to win. But I had a plan in mind.

It was the first Friday of October. After a long day at work, and a short nap, I felt good and energetic. I took a shower and cleaned up well and put my make up and slutty dress on with my cleavage showing. I grabbed a few condoms and put them in my purse along with my cannabis gummies. I love cannabis and it always makes me more social and relaxed, not to mention hornier. I checked myself in the mirror and made sure I looked like a sexy girl from head to toe.

There was a bar near my house and I decided to start there. It was shortly after 9pm and there were a number of guys and girls hanging out, drinking or flirting with one another. I approached the bartender and ordered a martini. Ten minutes later, a girl came and offered to buy me a drink. She was a hottie and if it was any other night, I would have gladly accepted her offer, but I was on a different mission. So, I politely rejected her and told her that I was waiting for someone. She left and immediately after that, a nice gentleman took her place and sat next to me. He was about an inch taller than me, with a nice smile and a few grey hairs, in his mid 30's. I remembered him from the moment I entered the bar and our eyes locked for a second. But at that time I did not consider him as a candidate.

"Is this seat taken, or is your friend coming back?" he said politely.

"She was not my friend, I am by myself" I replied while taking a sip of my drink and acting aloof.

"Oh, how is it possible to be this sexy and without company?" he asked half surprised, "May I be your company for a few minutes and buy you a drink?"

"Hmmmm, sure, why not? But I am leaving soon. Gotta be somewhere later"

"Fair enough. I am Brad. Nice to meet you."

"Venessa, nice to meet you too"

I ordered another martini and he got himself a whiskey. We talked about some random stuff and I noticed he kept looking at my bare legs and thighs. This was a good sign, and I could tell that he was just a straight guy. So I swirled my stool a bit toward him and our knees started to touch gently. I could tell that he was obviously into me and was trying to keep the conversation going. However, it was time for the next step of my plan.

"Hey, thank you so much for that drink, but I think I have to get going now", I said it with a regretful voice.

"Oh no, we were just getting acquainted. Can't you stay a bit longer? Do you have a commitment to be somewhere?" he objected, almost begging me to stay.

"Well, not quite. I usually have a me night one Friday a month and tonight is that night" I told him to see how persuasive he would be to keep me from going.

"You can still have your me night, even if you leave in half an hour. Let me buy you another drink in the meantime" he suggested.

"No, thanks. Two drinks is my limit for the night. but tell me, are you okay with pot?"

"Hell yeah, I love the feeling of high"

"Then, let me treat you to a little bit of weed" and handed him a gummy. We both took our gummies and I agreed to stay a bit longer. So far, my plan seemed to be working well.

After half an hour, I told him that I wanted to leave, but also asked him to walk me home and he gladly accepted. The walk was somewhat short, and we got to my door quicker than he expected.

"Thanks for walking me home. I appreciate it" I said with an innocent smile on my face.

"You're welcome, but I am sad to end the night with you so soon. What are you going to do once you go upstairs?" he asked.

"I am gonna smoke a joint and watch Sex and the City"

"Sounds like a nice plan. Any chance I could join you?"

"Maybe not. We just met"

"Can I at least kiss you?"

"Well, since you asked so nicely" and I closed my eyes and let him approach and plant his lips on mine. He had very soft lips with nice pressure. We kissed for a while and I noticed he was pretty excited and aroused. I was not doing any better myself.

"Tell you what. I am going to bend my own rule a little tonight. You may come upstairs for a while and hang out. But it is still my night and I decide when the night ends, not you. So, you leave if I ask you to leave, and you stay if I ask you to stay. Promise?

"I promise" and he hugged me, making me laugh.

We got upstairs and smoked a joint which immediately made us both high. He sat next to me and we started to make out. He started to grab my boob and massage it and I stopped him.

"I don't think we should go any further than this. I don't think you are ready to handle me" I said firmly.

"What makes you say that? I think I am gonna do just fine" he objected.

"Believe me, I am too much for you"

"No way. You are just what I want"

"Are you sure?"

"I am positive"

"Okay, but once we start, we go all the way"

"Haha, let's do it baby"

"As you wish", I smiled and thought that my plan was going very well, "Okay, take off your shirt for now and help me take off my bra"

He gladly obliged and we laid down on the bed and continued to make out. I admit that he was a wonderful kisser and his moves with his tongue and lips kept changing. It was like making out with 5 different people one after the other. I was definitely getting hornier myself and my dick started to get hard, something that I still did not want him to see.

"Lay down and close your eyes" I told him. I wanted to keep my own penis out of sight for now. I started to kiss his chest, nipples, and moved further down to his belly. I then unbuttoned his jeans and asked him to remove his pants and underwear and socks. He followed and laid down again completely naked.

I have been told by several guys that I give great blow jobs. Perhaps it was because I had a dick myself and I knew its sensitive spots. So, I started to go down on him and take his somewhat large dick in my mouth. He started to moan and move up and down.

"Stay still baby. Let me do the work, you sit back and enjoy" I commanded him. But as he was getting more and more excited, I decided to stop and have him play with me. So, I got up and stood half naked in front of him.

"Come here baby. Will you pleasure my body from head to toe without an exception?"

"Hell yeah," he jumped and stood in front of me"

"Start from the top and as you go further down, undress me too"

We started to make out again for a while and then I gently pushed his head down toward my boobs and already hard nipples. My nipples have always been sensitive and I loved having them being sucked and licked. He licked my nipples for a while and went further down. He then grabbed me and landed me on the bed and before I realized, he grabbed my feet and placed them on his face and started to smell and kiss them. This was definitely a first for me. I once kissed a girl's toes in a playful way and that was about it, but never had anyone kissing and licking my feet before, and frankly I absolutely loved it. Brad seemed to enjoy it even more, so I decided to make him beg for my feet later.

"You like my feet, I see. Do you have a foot fetish or something?" I asked enthusiastically.

"Well, I like nice feet, and I don't think I have a foot fetish. but when I looked at your feet at the bar, I absolutely loved them and when you said I could play with your body from head to toe, I thought you had an intention to bring up toes, so I went for it, and the more you liked it, the more excited I got"

"You kinky boy. I did not have any intention, but I like where your mind went. Who knows? Maybe you can handle me after all" I winked at him.

He grabbed my foot again to lick it, but I stopped him.

"I might let you play with my feet later, but for now, there is another part of me that needs attention" I smiled and looked down. It was time to reveal my secret.

"My pleasure" he said and started kissing my leg from my ankle up. As he reached my panties, he grabbed and started to pull it down. I was looking at him, not sure what his reaction would be.

"What the hell? Are you a dude? Shit, shit, you asshole, you tricked me" he screamed at me.

"Baby, when did I trick you? Tell me how I lied to you" I calmly responded.

"Well, I mean you never said you had a dick"

"But I never lied honey. I even told you I am too much for you, and you disagreed"

"I thought you meant something else, like you are too kinky in bed"

"Haha, that for sure is true. I really am kinky in bed"

"No, I can't, I can't do it, I like girls only"

"But baby, I am a girl. Until a minute ago, you just saw me as a girl and enjoyed being with me. What is bothering you is the taboo to be with me. Otherwise, I am still the sexy lady you liked at the bar, and yes, fun with me will be different, but still fun, I promise" and winked at him.

"But, I mean. If you do, No, no way. What if I like it? Damn it"

"So what if you like it? What is wrong with any of it? It would not make you any less straight than you already are. You will just have a unique experience that lots of straight guys are dying to have."

"But...." he stayed silent. He was definitely torn and I could see that he was considering to stay.

"Don't forget you promised to stay if I asked you, and I am asking you to stay" I told him while smiling, "Give me 10 minutes and leave after that, if you are not having fun, but for 10 minutes, let go of your ego and just go with the flow. Okay honey?"

Silence....

"I can't believe it. But okay, I will stay for 10 minutes" he finally agreed.

Right around this time the gummy that we took an hour ago started to take effect and I noticed a boost of high in myself, and he seemed to feel its effect as well. I told him to lay down on the bed next to me and close his eyes. Once his eyes were closed to neared my face to his face and gently kissed him. He was a bit motionless, but he slowly started to kiss me back, which was a good sign. We kissed for a minute or two and I noticed his dick was getting hard. He was definitely horny and in the mood, he just needed to accept the new reality. I grabbed his hand and slowly moved it to my dick which was half hard. Surprisingly, he grabbed my dick in his hand, but did not move his hand. In turn, I too grabbed his dick and gently started to rub it. The combination of the hand jobs and our kisses started to make us both moan and salivate. A minute later, I stopped kissing him...

"Would you like to go down on me?" I asked suggestively with a flirtatious smile of an innocent girl.

"I don't know, probably not" he said it as if he was guilty of something.

"Honey, do you remember that we agreed that once we start we go all the way?"

"Yeah, but that was before I found out about your dick"

"True. But can you admit, a part of you wants to try it?"

"Haha, maybe?"

"Good, With anything that is sexually taboo, there is also a level of excitement. Embrace that excitement and just go with it. If you don't like it after 30 seconds, we stop"

"Good thing you have a nice dick, well, okay"

He was not wrong. My circumcised dick is about 6 inches when hard, not that big, but a good size for a trans girl. I also always keep my body smooth and hairless.

I sat on the edge of the bed with my legs open and asked him to sit between my legs on the floor which he obliged. I wanted him to relax and ease into it at his own pace. He sat there, going back and forth and finally gave a little kiss to the tip of my dick. It was a good start, but he was still reluctant. Another kiss, and a lick followed next. But he was just slow and I started to run out of patience. I needed to push him a bit.

"It's been 10 minutes since we agreed to play. What do you want to do? Do you want to continue, or just leave?" I asked with an impatient voice.

"No, I want to stay"

"Good. Why are you still reluctant then?" I said with a calm voice.

"Believe me Vanessa. I am trying, but it is not easy for me to suck a cock."

"What about sucking on my toes first?"

"Yeah, I'd like that"

"Awesome, I am going to let you worship my feet a little" I said and moved back in bed and laid down. My feet were almost dangling out of the bed. He was still in his position, he started to smell and kiss my right foot, licking each toe. His wet tongue crawled between my toes and it felt amazing. I am sure being high made it much better too. I felt empowered and sexy to have a straight guy licking my toes and getting excited because of it. He started moaning and breathing harder. He stood up and grabbed both my feet and placed it on his face and started to lick my soles. His dick was hard as a rock. I was moaning and breathing harder myself. I let him worship my feet for another minute. Then I used my right foot and gently slapped his face a few times.

"Having too much fun are we? How are you feeling dear?"

"Very good, damn you have gorgeous feet. I can't get enough of them" he replied.

"Glad to hear. I never knew foot play could be this much fun. But now I want you to start kissing my body, start from my ankles and move up to where you know" I commanded him. He said okay and started kissing my feet, my ankles, my calves, knees, thighs. We both knew he had reached the point of no return and he was about to give his first blow job. He reached to my dick which was so hard from the excitement of the moment.

"Can we turn off the light?" he requested.

"No honey, I want to look at your face as you suck on dick" I said, hoping he would not object and he did not. He started kissing around my dick first, and then started kissing my balls. Finally he opened his mouth, inserting my penis inside his mouth. It was a surreal moment and I could not believe it was happening. I mean I had been with other bi or gay guys and received blow jobs many times, but never with a straight guy. This was an exciting achievement. For a first timer, he was doing a decent job, his rhythm was nice and his lips and tongue had nicely sandwiched my dick in his mouth. Interestingly enough, he seemed to like it too. How did I know? His dick remained hard and he was not stopping.

"Well hello, how are we doing?" I stopped him to ask.

"Maybe it is because I am high as hell, but I am enjoying it more than I thought," he said with a big smile on his face.

"See? I told you to just go with the flow. You ain't seen anything yet. It will only get better."

"It gets better, if we do a 69" he suggested with a wink.

"Haha, my naughty boy, let's 69 then"

He laid down and I got on top of him. Thankfully, he was very well trimmed and barely had any pubic hair. Good, because I preferred smooth dicks and butts. I opened my mouth and took his cock into my mouth and he did the same. Whenever I do a 69, my main focus is the blow job that I give and I care much less about the blow job that I receive. But this time was different. I felt as if a wave of pleasure was circulating from my mouth to my dick and back, and it was amazing. However, I could not multitask much longer and stopped blowing him, and just allowed him to pleasure me. The guy who was about to leave just a few minutes ago because of my penis, could not get enough of it. He then left my dick alone and gently licked my smooth balls"

"Do you like rimming?" I asked him with a curious voice.

"Depends on the situation, but sometimes I do"

"What about now?"

"Hummm, maybe?"

"Maybe?? Okay let's not do it then. I pressured you enough for one night, I don't wanna overdo it" I said it while keeping my ass inches above his face. He was obviously looking at my cute and tight butthole, and deciding.

"You know what? I sucked your dick, so I might as well lick your butt hole too" he announced.

"Nope, not unless you really really want it"

"I am telling you I want it"

"Yeah? Then ask for it. Beg for it"

"Can I please rim you Vanessa? I really want to do it"

"Well, since you asked nicely" and I lowered my ass a bit and stopped. He still had to raise his head to lick me. He did just that and started to lick my ass. If you have not been rimmed before, I highly recommend that you try it, it is definitely a unique sensation. As he licked my butthole more and more, I lowered my ass and sat on his face. I could tell that he liked it a lot. He grabbed my dick with his right hand and started rubbing it as he rimmed me. This went on for a while.

"Honey, are you sure you are straight? You seem to be enjoying my ass and dick quite a lot" I teased him as I got up to let him breathe a bit.

"No kidding. I am surprised too, but I just followed your advice and stopped overthinking it and now I am having a blast."

"I could tell you liked that I sat on your face"

"Yeah, I like it when girls sit on my face"

"Hey, I am a girl. Don't you forget it. I can just be more fun than a typical girl. I can do things that they cannot. Wanna try it?"

"I am afraid to say yes, because I think I know what it may lead to"

"Sweetie, it leads to us taking turns and fucking each other"

"Yeah, that is what I was afraid of. I don't think I wanna to get fucked. Besides, I thought trans girls only like to get fucked." he said.

"Depends on the girl. Yes, the bottom girls only like to get fucked. But I am a vers" I replied

"What do you mean by vers?"

"Oh, vers is short for versatile. A vers trwns girl likes to fuck and be fucked both" I explained "Also, you did not want to suck my dick and a few minutes later, you could not leave it alone buddy. Sooooo, that happened"

He chucked and I laughed too. I suggested smoking a joint and he agreed. Two minutes later, we were high and horny again.

"Like before, don't overthink it. It may feel weird at first, but once the pain goes away, you will feel a pleasure like nothing you experienced before" I told him.

"Can we start with me fucking you first?" he asked.

"We can, but if you cum, you may no longer be horny to continue. I, on the other hand, get even hornier and want to bottom after I cum, so it works better for both of us this way"

"Good thing I am so high, I cannot think straight" he said and laid down.

"Good. Just one thing, are you `clean` down there?" I asked.

"Oh that. Yeah I am. Trust me" he replied.

"That is good enough for me. I am too"

"Are you gonna rim me too?"

"I would honey, but I am not into licking hairy ass holes"

"I am not hairy, check for yourself"

He was right. His ass was hairless. I did not ask if it was naturally that way or he maintained it that way.I was just happy to see his hairless ass cheeks. I made him spread his legs and gave him a nice blow job, followed by a warm and wet rim job. Then I moved up on his body and laid down on him and we kissed for a while. I needed to relax him again, the next step would be a huge one for his psyche. After some kissing, I got up and grabbed my lotion. I asked him to suck my dick a bit to get me hard and he gladly did. He was less resistant than an hour ago. I think he seriously decided to explore the night with me fully.

I placed a pillow under his butt, put a condom on, and applied some lotion to my hard dick. He obviously seemed nervous. So I kissed him a bit more.