I'm Bob, a recent high school graduate trying to decide what to do with my life. I'm still living with my parents and will be going to a local community college. I like girls but haven't had much luck. I've had a few dates but never had anything lasting. I'm ashamed to admit that I've never gone all the way with a girl. We've had some making out and actually was naked with a girl once, but it just left me frustrated. I was disappointed to find that girls aren't very keen on blowjobs, but one gave me a hand job.

I've enjoyed girl's bodies, and several have let me suck their nipples. I tried to go down on one girl but she stopped me because she thought it was "dirty". When I got close I could tell she smelled fishy, so I backed off like she wanted me to. But what I liked the best about a girl was her sexy ass! As I watched bikini-clad girls at the beach I spent more time admiring their asses than their tits. Unfortunately most girls didn't like me messing with their ass, at least beyond squeezing their cheeks.

Okay, so now you know I like girls but haven't had much success. I feel like I've tried nearly everything, and then an idea hit me. There is a local bar that people said was a gay bar, so I kept my distance. I had heard that they had drag queen shows on Friday and Saturday nights, and I wondered what it would be like.

Now I know darned well that the drag queens are just guys dressed up as girls, but heard they were very convincing. I wondered if I might get lucky and maybe get a blowjob, which I heard gay guys loved to give. I felt nervous about going to a gay bar, and feared someone I knew would see me. I started to fantasize about getting a blowjob from a drag queen whenever I jacked-off, and I came more strongly each time, though I did feel a little guilt right afterward.

By Friday night I was fully committed to go, and cautiously entered the bar. I paid the cover charge and was seated alone at a small table and ordered a beer. The beers drinks were expensive, so I nursed mine to make it last. When the show started I was captivated – I knew they were guys but they looked so good and were incredibly sexy. My hard cock strained in my pants. I'd have to deal with this when I have to go to the men's room, but for now I was just enjoying the show.

"I haven't seen you before," said a voice to my left. I looked up and saw the most beautiful girl ever – with long reddish brown hair and lovely blue eyes and a smile I couldn't resist.

"My first time here," I said, smiling back at her.

"I'm Briana," she said, "May I join you?"

"Please do," I said, "I"m Bob," I thought she was there to encourage me to buy more drinks, and I resolved to resist, though I did find her difficult to resist.

Briana already had a drink, so my frugality was not yet tested. She sat down and we began to get acquainted. "Are you a performer here?" I asked.

"No, I'm just a customer," Briana said, "just looking for someone nice."

"Same here," I said, surprised that I would find the right girl here. I wondered if she really was a girl or a drag queen as well.

"Briana, I don't know how to ask this," I said, "I'm not so good at talking with girls."

"You're doing alright so far," she said, smiling, "What's on your mind?"

I couldn't just ask her if she had a dick, but didn't know what words to use, "Are you like the girls on stage?"

"Oh heavens no!" said "I'm no performer, and I'd be scared to death up there."

"That's not exactly what I meant," I said, blushing with embarrassment.

"You want to know if I'm a real girl," Briana said, "What do you think?"

"I can't tell," I admitted.

"Then what difference does it make?" she responded.

For now, it didn't matter, but it might later – depending on how things go.

We were both silent for a while after that and sat there watching the show. I found myself holding Briana's hand and really liking it. I thought about my jack-off fantasy and wondered how to get to that situation. Where would I take her? My car? Just how do I ask her to suck me? Damn, it's so hard to talk to a girl!

I was surprised when Briana suggested that we leave and go for a walk. That satisfied me that I knew she wasn't just there to mooch drinks, and who knew where it could lead?

We left and walked along the sidewalk, and Briana took my hand in hers. I liked holding her hand and was sure I'd like other things about her as well. She was so pretty I really wanted to kiss her but was timid about it. I didn't know if she would welcome it, and what if she wasn't a real girl?

We stopped at street corner and waited for the traffic light to change. I looked at her pretty face and was filled with desire. I decided I would assume she was real and I leaned to her and kissed her pretty lips. She responded wonderfully by slipping her tongue into my mouth and we enjoyed a thoroughly shared kiss.

"Are you straight," Briana asked.

"Yes," I replied with conviction.

"Good," she replied, "I like straight boys. Are you looking to get lucky tonight?"

"I want to enjoy being with you," I said, "But if I get lucky, that's good too."

"Thank you for being honest with me," Briana said, "If you said you didn't want to get lucky then I'd know you would lie to me about other things as well."

I kissed her again and she seemed more passionate than before.

"So Bob," she asked, "If you were to get lucky, would you prefer a blowjob or to fuck my ass?"

I couldn't believe what I was being asked, and found myself speechless.

"Oh, what kind of girl am I?" she asked, "You don't even know what my ass looks like!"

Briana took out her phone and pulled a picture to show me. It was her bending over, panties down and dress up. She had an ass to die for!

"I sure like what I see!" I said, smiling.

Briana grinned back at me and said, "You must be an ass-man – most guys would rather have the blowjob."

"Guilty," I eagerly admitted.

"You don't seem like most boys," she said, "And I hope I'm right about you."

"I hope so too," I agreed, "But what is it you don't like about them?"

"With them it’s all one sided," she said, "As soon as they cum they are out the door, leaving me to myself."

"That's stupid to do that to a girl," I said, "Why would they do that?"

"Some are just selfish bastards and leave once they got what they wanted," she explained, "and some feel guilty and just want to escape."

"Guilty? Why would they –" I asked, "From cumming?"

"Haven't you ever felt guilty right after you came?" asked Briana.

I thought about it a bit and realized that I had felt guilt after cumming when I had fantasized about taboo things, like doing it with my mother one time. Then it hit me. They felt guilty about doing it with a guy. It sure seemed like Briana was a girl, but if she was a guy, it would matter if I had to satisfy her.

"Briana dear," I said, "I'm not very experienced with girls – I've only done a little – in fact I'm still a virgin, but I don't have any experience with a girl like you."

"Getting cold feet?" she asked, "It would be a lot more honest of you to admit it before you cum rather than just use me and bolt out the door."

"Briana, this is all so new to me! I like you but I'm a little scared as well. I don't want to be like those other guys. I have an idea but I don't know if it will work."

"I guess I've really ruined the mood for you," Briana said, "Would you like to come to my place for a drink and see if we can rekindle the fire?"

I quickly agreed and Briana led me to her nearby apartment. She mixed a couple rum and cokes for us and we sat on the couch together.

She sat close to me and we kissed. Her hand was on my leg, squeezing my cock and my hand was on her knee, not sure if I dared go further.

"It feels like you need some relief," observed Briana, "So tell me the idea you have."

"I don't know how well this would work," I began, "But I thought if I took care of you first it would be fair for you too."

"Would you do that?" Briana asked, "Other guys didn't – maybe because they were so eager to cum."

"I don't know exactly what to do," I admitted, "This is all so new to me."

"How about if we start with my ass?" asked Briana, "You seemed really interested."

Briana got up and knelt on the couch facing the back. She told me to kneel on the floor, which I did. "Lift my skirt," she said.

Cautiously I lifted the skirt, exposing her pantied buns. Other girls never let me indulge my kinky desires. My heart was racing as I saw her panties and my desire grew. Briana reached back and pulled her panties down to the bottom of her cheeks. I had always found pictures of buns arousing, but never had seen them in real life before. I was pretty sure Briana was a boy, but I was looking at a girls ass right now, and loving it!

"Go ahead and kiss me there," directed Briana. I was stunned. I really wanted to but had never done anything like that before.

"Losing your nerve?" she asked, "Take out your cock and stroke it."

I quickly had my cock out and stoked myself to erection and found myself drawn to her buns. I lovingly kissed her roundness and alternated cheeks, each time moving closer to her crack. I paused at her crack and kissed there as she said, "Yes, lick me there."

This seemed really kinky, but I was really aroused and my little head seemed to be controlling me. I kissed up and down her crack and extended my tongue between her cheeks. Briana reached back and spread her cheeks and I saw her hole for the first time. This was so much hotter than any pictures I'd seen and I just couldn't resist kissing her there.

As my lips touched her sensitive pucker Briana exclaimed, "Yes, that's it – oh please do more!"

Kissing her ass hole seemed the most perverted thing I could do, but I wanted to so badly. I kissed her hole as if it were her mouth and soon extended my tongue in. I feared that I'd have some unpleasant surprises, but Briana was wonderfully clean.

Briana seemed to like it even more than I did, and she squirmed and moaned as I kissed her. I wanted to slip my cock into her ass. Soon she said, "Ready to make me cum?" I just continued to kiss her deeply.

Briana got up from the couch and slipped her panties off and turned around. There was no doubt now that her hard cock bobbed inches from my face. "Please do this for me and I'll take good care of you," she said.

"I'm sorry Briana," I blurted out, "I don't know if I can do this."

"Of course you can, Bob" she assured me, "You just had your tongue up my ass – this is easier, just start by holding me in your mouth – that's all."

I was still stroking my cock, which urged me to go on, and I tentatively opened my mouth.

Briana eased her cock into my mouth and I was surprised that it actually felt kind of nice – like it belonged.

"Such a good boy," said Briana, running her fingers through my hair, "Now keep stroking, and when you are ready, begin to suck."

I wasn't thinking rationally, but I didn't care. I sucked her and moved my tongue around and soon stopped stroking myself, an found my hands squeezing her soft buns. Without really understanding, I knew that I wanted this and i wanted to make Briana cum.

"I'm getting close and I think you are man enough to take it," said Briana, "So just swallow as I give it to you."

Sure enough, in a few minutes she pumped her load into my mouth. It was strong tasting – I wasn't sure I liked it but I swallowed as directed. I realized that I had just done something no straight guy would ever do, but I willingly did so – in fact I was still hard!

"You really aren't like other boys!" said Briana, "And you're still hard, so you must still want me."

"I want you Briana – more than I've wanted any girl!"

Briana brought her mouth to mine and tasted her load while grasping my cock and stroking. "Get ready to be lucky," she said.

"I already feel lucky," I said. Briana opened a condom and rolled it onto my hard cock and applied a generous amount of lube. Briana bent over, spreading her cheeks, and lubed her hole.

"Now enter slowly, Bob – it can really hurt if you go to fast," she said, "Once I'm used to you in me you can go as fast as you like."

I moved to her and brought my cock head to her hole, so aroused I was afraid I would cum to quickly. I pressed in very slowly, taking care not to hurt Briana. I must have been going too slow because she pushed back, causing me to slide in all the way. Briana tightened around me a couple of times and I was in heaven! "Now go for it!" she said, and I began to stroke.

The feeling was wonderful and the view was incredible! Briana continued to squeeze her ass muscles around me and it didn't take much for me to climax, emptying inside her as I pulled her hips to me.

I immediately felt a rush of guilt wash over me, but resolved that I wouldn't let it control me.

"You doing okay?" asked Briana, and I nodded.

"Are you feeling any guilt at all?" she asked.

"Yes, but I'm not letting it control me," I replied.

"You aren't like other boys!" she said, "Thank you for treating me with respect – you don't have to kiss me if you don't want to."

"I do want to," I insisted, "And I want to see you again if you are willing."

"I don't plan on letting a boy like you get away!" assured Briana. She gave me her phone number and told me to call any time I wanted.

I got dressed and took Briana in my arms. We kissed and I fondled her soft buns. She may not be a regular girl, but she gave me what no other girl had! We finished kissing and I left for home.

For the next day I found I just couldn't get her out of my mind. I couldn't resist calling Briana. She was at work and couldn't talk just then, but said she would call back in fifteen minutes.

When she called I was in a secluded area where we could talk privately. I asked her if I could come visit and she said that she would be home at five, but she would be in boy-mode, and asked if that was okay. I hesitated, and she said, "Maybe that isn't such a good idea – maybe another time."

"No, please, I want to," I insisted.

"Why would you want to see me like that?" asked Briana.

"I like YOU," I explained, "Not your clothes – don't get me wrong, you looked wonderfully sexy, but the clothes aren't YOU."

"Bob, once again you impress me with how different you are!" Briana responded, "Come by at five."

I was thrilled to see her again, but then it hit me that I would be meeting a "he", not a "she". I began to feel nervous and wondered if I should bail out. Going to meet a girl was one thing, but I would be going to meet a guy, and I wasn't sure I could handle that.

I was undecided for a while but realized that if I ever wanted to be with Briana again I had to go through with this. I braced myself for seeing Briana as a boy and decided that it wouldn't be a romantic encounter this time.

I arrived at Briana's apartment a little after five. As expected, a boy answered and smiled at me. "Hi, I'm Brian," he said, "But if it makes you more comfortable you can still call me Briana."

"I'll call you by the name that matches your appearance," I said, extending my hand.

Brian shook my hand and said, "I didn't expect a kiss, but I'd still love to kiss you."

"This is a very strange situation for me," I said, "Give me some time." I wondered if I could bring myself to kiss a guy – kissing Briana was easy and hot!"

Brian made us a couple of rum and cokes and we sat on the couch and talked, but this time with some space between us. I thought Brian was gay, but he explained that it wasn't quite that simple. He considered himself to be "gender fluid", enjoying being male sometime and female other times.

I had heard of transgender, but this was different. Overall, it seemed like a good arrangement for Briana because she had a lot of options.

Brian explained that being a male was an advantage when it came to employment and other male-biased opportunities but loved the wonderful diversity of clothing available to women.

"I really want to kiss you Bob," said Brian, "But not like this – would you wait a bit while I change, and can be with you as Briana?" I eagerly agreed and Brian excused himself after making me another rum and coke, telling me it may take a while.

While I waited I tried to imagine what Brian was doing to become the lovely Briana. I watched TV while I waited, and after an hour the beautiful Briana greeted me. I immediately stood up and took her into my arms and kissed her. I knew in my head that I was really kissing Brian, but my heart said it was Briana.

"What do you think now?" she asked.

"I like you better like this," I said, pulling her closer to me, squeezing her soft cheeks. As we kissed Briana reached for my cock and found me well-aroused.

"Thank you Bob, for being such a great guy!" she said, "I want to reward you and show you how much I appreciate you."

She unzipped me and took out my cock. Dropping to her knees, she sucked me. It was my first blowjob and was wonderful! I came quickly, and Briana eagerly swallowed my load. She took a sip from her drink before kissing me.

I knew I should return the favor, but wasn't exactly in the mood. Briana came to my rescue by saying, "Don't worry about me right now – I just wanted to show my appreciation."

I came home feeling wonderful about Briana, even though she wasn't like most girls. She was certainly a lot more fun than any girl I'd been with – and she seemed to understand me in a way that girls didn’t. Part of that difference was great, and another part wasn't. I felt like I was getting into a gay relationship while hiding it from myself.

The more I thought about it, the more I realized that I really didn't mind being in a gay relationship, though I didn't want to be public about it. I really like girls, and REALLY LIKE Briana, but I'm not really attracted to boys at all. I sucked her off out of courtesy rather than desire, but I did look forward to doing it again.

That night I lay in bed thinking about Briana and how much I liked rimming her, even though she wasn't a regular girl. I found myself getting hard and began to stroke, and as I did, I kept thinking about sucking her. As I fantasized about sucking I sometimes thought about Briana and sometimes about Brian. When I came it was Brian I was sucking, and I realized that it was the cock I liked.

The next morning I awoke and about mid-morning called Brian and asked if I could see him. "Don't you mean Briana?" he asked.

"No," I said, "I want to see you – and maybe Briana too."

He told me to come over after lunch and I arrived promptly. He offered me a rum and coke and we sat on the couch. "Okay, what's on your mind?" he asked.

"Well, I really like Briana," I began, "But I know that it's really you, and I realize that it means I also must like you – but I'm not attracted to boys."

"That shouldn't be a problem," replies Brian, "We can just see to it that you date Briana and not me."

"That could work," I said, "But I was thinking it would be even better if it didn't matter."

"Are you saying you want to be a switch-hitter?" asked Brian.

"I don't know what I'm saying," I said, "It's all so confusing."

"Well, let's take it a little at a time," Brian said, "How would you like to start?"

"How about if I kiss you?" I asked.

"That's easy for me because I'm used to kissing you, but you aren't used to kissing a guy," Brian said, "So why don't you start out with your eyes closed and pretend you are kissing Briana – it's the same lips anyway."

I closed my eyes and felt Briana's lips pressed to mine. Our lips parted and our tongues met. It was wonderful, so I opened my eyes to see that it was really Brian and found that I continued to enjoy it. Brian pulled away and smiled, and then we re-engaged. He put his hand on my cock through my pants and said, "I can tell you're warming up to this already."

"I am, and I’m ready to go further – I want to suck you, Brian," I said.

"Are you sure you're ready for that?" he asked.

"I'm as ready as I'll ever be," I replied, "Please take your clothes off."

We both stripped down and I stood and pulled him to me, kissing once again and grasping his hardening cock. He did the same and soon we were both fully aroused. It seemed like a much better way for men to greet each other than shaking hands, but for now it was just between us.

I dropped to my knees and sucked Brian as I stroked myself. Brian came almost instantly, and I did shortly after.

As I swallowed his cum I realized that I liked Briana for her girliness, but Brian for his cock. We talked for awhile and agreed that while I would mainly date Briana, from time to time I would hang out with Brian and some of his friends. I'm not sure if that makes me gay, but I sure like sucking Brian while I sure like girls with dicks!

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)