My First Time

My First Time

"Jerry, you can't expect me to go along with this, can you? The thought of attending a mixer in a crowded club as a woman might be exciting for you, but I'm not drawn to that world, and I would prefer not to have that particular skeleton in my closet. Thank you, but no!"

"C'mon Phil, it's only one night and you know that there will be some real women there and maybe some great looking guys who might turn your head. Okay, forget I said that last part, but imagine the experience of seeing life through a totally different pair of eyes. After all the psychology courses that you took, the years of research and now having an honest, first-hand perspective like this will make you invaluable as a therapist one day. I'm really doing this for you," he said with a smile.

"You're good, I'll give you that and I can see you moving on to the 4:00am slot on local TV to sell aluminum siding or replacement windows, but I'm not buying it," I replied with mock annoyance. "If you want to go to a gay bar in drag, that's fine, I'll support your choice. I'll even take you there and pick you up afterward if you haven't hooked up with someone, but I would prefer not to go through the ordeal of transforming myself into something I'm not and fending off unwanted advances," I joked.

"Ah, the 'unwanted advances' frighten you, but you moved away from a definitive 'no'," he responded with a broad smile.

Jerry is my oldest friend; someone I have known since elementary school and my roommate since we graduated from college. He came out to me in high school and we remained close over the college years even though we went to different universities. I understood he was gay and knew of his fondness for dressing in women's clothing, hanging out with effeminate guys, and I even joined him at social get-togethers with his friends at times because they were nice, kind people and fun to be with, but we traveled in different circles for the most part.

"How about this," he said. "I will buy you a fantastic outfit and you can borrow my new strawberry blonde wig, and with proper makeup and accessories I guarantee that you will be the belle of the ball. In fact, if you aren't asked for a date by at least three guys, I will take you out myself, any restaurant you want, my treat. You can't get a better offer than that so what do you say?" and then he held out his hand for me to shake on it.

"You're the most intense person I know," I replied with a grin, "but because of your perseverance, I will meet you halfway. I will go with you as a chaperone, so things don't get out of hand but no outfit or wig."

He thought for a minute and came back with a counterproposal, "How about just a black pixie cut wig, some light makeup and sandals? Nothing outrageous but just a bit androgenous to show a willingness to fit in."

"If the makeup is very muted and subtle, I guess I would consider it," I replied.

"Great, then we have a deal," he said while grabbing my hand and then hugging me with a smile that went from ear to ear. "You're the best friend ever."

"I didn't agree, Jerry, I said that I would consider it," I replied as he walked away.

"You have never gone back on your word, Phil, so don't start now. I know just the 'look' for you and if you really like what you see in the mirror, I will even buy you the perfect outfit as a thank you after the fact. Maybe you will even want to wear it when you go on a date with me," he said with a laugh. What a conniving prick! I walked off to pick up some food for dinner and a nice bottle of wine to drown myself.

Jerry sent me a text later in the day to remind me that the party night was less than three weeks' away and that there was a lot of planning required. He signed off with a smiley face emoji and a heart. I responded by saying that I would like him to go over his plans with me tonight so that I know what I must do to prepare but never expected what he eventually told me.

"We must try different makeup to get the right shading to match the wig and your skin tone, you must get shaved smooth, head to toe so you don't show hairy arms or legs, and since you're shaving that much you may as well do the other bits. There are places in town that can deal with those things so it won't be as bad as you might imagine," he said. "You will look beautiful and I'm certain that you will have a wonderful time. Don't forget, I will be there if you have any issues or if you get your period and need a tampon."

"Fuck you!" I responded with a laugh. "You only said light makeup and what you now describe is a 'make-over,' not exactly what I agreed to."

"Details, Phil, details," he said.

Jerry made an appointment for makeup so that we could see what worked best and he had me get my ears pierced with cheap studs that will be replaced with an elegant pair before the party so I looked my best for a night out even though I would be dressed casually. I also got a fantastic pair of lace up sandals that would look nice with linen slacks and the matching top that he insisted that I get to complete the ensemble.

We did a trial run on makeup and the ladies in the salon did a very nice job. Having now seen how the colors looked, they promised to improve upon it the day of the party after all the grooming was finished. Jerry made an appointment for his makeup as well and we arranged for pink French tip manicures and pedicures, something that I had never considered beforehand.

The remaining days leading up to the party went quickly and all our preparations paid off. Before Jerry and I had to leave we had time to sit around the apartment with a glass of wine, liquid courage for me and a primer for him. He was wearing a strawberry blonde wig, with light-colored makeup that was suitable with his emerald green mini-dress, and decorative black stockings; we both had pale pink lipstick to match the nails, another forgotten detail.

As we checked each other over in a final inspection, Jerry walked over and leaned down to me. "Phil, thank you for doing this with me. You are making this a special night, and I hope you have fun as well," he said as he kissed me on the cheek.

I smiled at him and replied, "I'm actually glad that you pushed me out of my comfort zone. I'm finding this strangely exciting and look forward to the evening as well but don't leave me alone too long, just in case."

"In case of what, Phil? In case you find someone who really excites you and you decide to throw your panties to the wind and follow your heart?" he said with a laugh. "Don't worry, I'll be right there."

We drove over to the club located about fifteen minutes from the apartment. It is a gay club well known in the area for its music and drag shows, and weekend events like this, mixers where people meet to hook up or simply to connect for future dates. Having a lot of people in drag gives the impression of a party atmosphere that blurs a lot of lines. The main idea is to have fun and mingle with like-minded individuals. There is a twenty dollar cover to keep out the simply curious but as I found out, this policy is flexible if the bartenders believe certain people are nice to have around for financial reasons and waive the cost of occasional drinks to offset the cover. Our first drink was comped as the bartender had previously taken a liking to Jerry, so things were improving already.

The dance floor became a little crowded as the night progressed but people squeezed in and found space to move around suggestively, and the music in that area never stopped. After a little while, a nice-looking fellow came up to Jerry at the bar and asked him to dance, an eventuality that Jerry and I had not discussed beforehand, but which seemed appropriate in light of the venue. Jerry wiggled away with him and appeared to be having fun; this made me happy for him and glad that I came along. I moved with the music as I stood by the bar in my new persona with a drink, talking to people around me. I never felt uncomfortable or self-conscious because I was happy and relaxed.

As the evening progressed, I was getting very warm from the combination of alcohol and music and barely noticed when a nice-looking man approached me from behind to get to the bar. He looked at me, leaned in and said, "You seem to really be enjoying the festivities and the crowd if I read the look on your face correctly."

"Yes, I am," I replied. "It's unique for me and I find it exciting if I am honest. How about you? Is it what you expected?"

"Yes, pretty much, except for you. I have been here for these mixers before and know that it will get better later if you remember to pace yourself," he replied then added, "You look very pretty by the way and I'm glad to have bumped into you."

"Thank you, you made my evening as well,' I said. "I feel good, too, and not just from the alcohol," and my words were met with a smile. Shortly after this brief exchange, another fellow walked up and asked if I would like another drink. He was pleasant enough, so I agreed, and we started chatting about life in general and had a few laughs in the process. He was joined by a friend and I introduced them to Jerry and we spent a pleasant hour or so before they wandered away to see some other acquaintances. I guess this is how it works and without an immediate connection or the guarantee of a hook up, people drift off somewhere else where the prospects might be better.

Jerry went to the ladies' room and came up behind me when he returned, placed his hands on my hips to pull me close and whispered in my ear, "I think the guy you were talking to was interested in you. Did he say anything?"

"He was pleasant enough but noncommittal. I guess he expected someone more direct but I was unprepared for that type of conversation and was a little stiff I guess," I replied.

"That's too bad, he looked nice and you would have made a sweet couple," Jerry said with a sly smile.

"I'm not sure that he really liked me," I said with a twinge of sadness in my voice.

"I'm surprised since I think that you are the most beautiful person here. I thought you would have guys eating out of your hand by now," he responded with a smile before gently nibbling my ear.

"You're being kind," I said, "I'm not worried and I'm having a nice time meeting friendly people and moving to the music. Don't worry about me, I'm fine."

"Well, that's nice to hear. But out of curiosity, what would you do if a guy asked you to dance or wanted to kiss you?"

"If he seemed nice enough I honestly would consider it the way I feel now," I said.

"Wow! That's quite a change in just a few weeks. What caused it?" he asked.

"Preparing for this event with you got me more deeply involved with my feminine side and now that I'm in this environment and see how people relate to each other, I am more comfortable with things I might not have considered before. The prospect of dancing with a man or even kissing him doesn't seem off-putting. It's hard to put my finger on exactly how I feel Jerry, but if a pleasant guy asked me on a date to have dinner with him, I would not refuse automatically."

"Really? A man just has to politely ask you out to dinner, and you would consider it? And if he wanted to kiss you, maybe on the neck or other places, you wouldn't object and would let him?" he said softly.

"The way that I feel now, yes," I whispered with a laugh.

"This could be one of those times that would be very difficult to walk back" he said. "It's your first time at a club like this and already you're weakening," he said quietly. "Are you sure this is what you're ready for?"

I hesitated for a minute then looked into his eyes, "You will have to ask me out if you want to know the answer for sure," I said.

Jerry pulled me to him and gently kissed me on the lips. My lips soon parted and he slipped his tongue into my mouth and for the first time, I could feel the passion that I secretly harbored for him. As we separated and Jerry thought about his next words, a nice-looking fellow came up to him and asked if he would like to dance. I saw the hesitation in his eyes, but he ended the indecision by simply saying that he needed a break right now but maybe later.

"Thank you, Jerry, you're a gentleman," I said before kissing him.

"I seem to have missed my chance with you," a man on my other side said so I would hear.

"Tonight yes, but perhaps another time," I replied as I looked into his eyes.

"I will hold you to it," he said with a grin. "My name is Steve and I would enjoy getting to know you, maybe for coffee or over lunch. May I call you?"

I smiled at him and replied, "I'd like that. My name is Pia and if you hand me your phone I give you my number."

After giving Steve my number, I turned back to Jerry and he said softly, "You work fast. Have I told you how lovely you look tonight?"

"Maybe, but I like hearing it anyway," I replied. "And please call me Pia. I like that name better right now since Phil wouldn't be here wearing makeup, nail polish, dangling earrings, a sheer top, lace-up sandals and a wig while giving his phone number to another man, right?"

"Phil isn't here tonight in case you haven't noticed," he said sternly. "But is Pia comfortable going home with a woman in a slinky dress that she just met after drinking in a gay bar?"

"Between us, I think Pia is a bit of a tramp and probably horny as hell so she wouldn't mind," I replied with a laugh.

"I've heard that tramps have the most fun anyway," he said, "but what do I know?"

"Probably a lot since you look quite slutty yourself," I replied.

"Eat your heart out, bitch," he hissed, and we both laughed.

It took another half hour or so for us to leave but when we got back to the apartment and stopped the car, I joked by asking him if he wanted to come up for a nightcap, and added that he could stay over if he wanted to rather than driving home late at night. "So, after weeks of complaining and all that I have put you through to get you here, you're asking me to spend the night with you. Do I understand you correctly or am I dreaming?" he said quietly.

I leaned over and kissed him, teasing his lips with my tongue, and whispered, "Don't think about it too long or I may get offended and withdraw the offer. I feel fragile now but tomorrow morning Phil may come back to curse you. Right now, you have a choice: Pia the loving tramp tonight or Phil your grumpy friend tomorrow. The choice is yours, but I know which one I would choose if I were you."

"Finish parking the car and let's go upstairs," he said. "It's late and I've had a few drinks so it's better if I get out of this tight, skimpy dress, stockings and panties, and lie down for a while," he said softly.

"I'll join you if you help me with my blouse and slacks," I offered.

"Aside from looking like a beautiful princess, you act like one. Help you with your slacks, really? Fucking Prima Donna!" he responded while laughing.

We entered the apartment giggling and when the door closed Jerry held me close and kissed me passionately. "I've wanted to do this for so long," he said.

"I didn't know it, but I now realize that I wanted you, too," I replied. "Thank you for finding the means to get me to the club with you. I never imagined that this would happen, but I am so glad that it did. I feel free and I enjoyed the emotions that came along with the freedom. Please remember that I am new to this and go easy with me. I want to experience everything with you, just a little slowly."

I helped Jerry remove his dress and underwear and once he was naked he helped me take off my blouse, slacks, stockings and panties as well. Taking off the wigs left us just two young men with erections in desperate need of attention and Jerry pushed me onto the bed before kissing me deeply as I lay on my back. He pushed his tongue between my lips until it met mine and then he gently sucked it. He held my head and kissed my neck, working his way down to my nipples. Teasing and nibbling each one in turn, he brought me very close to the edge before moving down my stomach to my abdomen. Slowly, he took my hard cock into his mouth and let it slide down his throat and then moved rhythmically up and down bringing me ever closer to the orgasm that I desperately desired. I placed my hands on the sides of his head to hold it still while I proceeded to fuck his throat energetically while moaning loudly.

It didn't take very long until I felt the muscles in my abdomen starting to contract followed by the pulsing of streams of semen into Jerry's mouth and rapid swallowing on his part. I held him until the pulsing ended and I was drained, then rolled over and moved to take his stiff cock into my mouth, a first for me. I lifted my head and softly said, "You are my first and I am glad that you are. I couldn't imagine doing this with anyone else."

With my inexperience, I simply made my own path, kissing him, nibbling his nipples and listening to sounds that he made in response to my movements. Luckily, Jerry was easily aroused and it took less than a minute for me to adjust to having his erection in my mouth and then I began to move up and down on it which excited me as well. Any reluctance that I may have felt disappeared and soon I had the full length of his stiff dick going in and out of my throat. I squeezed his nipples while I sucked his cock, and I enjoyed the experience of bringing him such intense pleasure. He held my head like I did to him and moved my head up and down until he held me tight and released a load of hot cum into my mouth. I enjoyed the taste and eagerly sucked him dry while he spasmed and forced every drop into my mouth for me to swallow. It was a wonderful experience and I enjoyed bringing satisfaction to someone I cared about.

Jerry turned around and put his arms around me, kissed me and held me close, a feeling that I appreciated as we slept together like this most of the night. In the morning, we showered together and satisfied each other orally under the warm water. A different life awaited me, one that I longed to experience.