My First Time Pt. 02

My First Time--Part 2

At the end of the workday, I found myself struggling to go home. I remained conflicted by what transpired with Jerry and the night partying at the gay club in general. I had behaved differently from any other time in my life and Jerry and I spent the night together, had sex and showered, and had sex again in the morning. I surprised myself but strangely I was not upset by what happened; what has been troubling me was that I was unsure what to expect going forward. Scenarios floated in my mind and usually ended nowhere. Is this how a life-changing moment is meant to play out? I followed the principle that you think before you act and once a decision on a specific course of action is taken, you follow it through without second thoughts. Why don't I feel this way now? If I was confused about myself as a person before, I am totally scrambled now.

When I entered the apartment, Jerry was already out of the shower, enjoying a beer in the living room. He looked up and said lightly, "Hey, what's up? You look like you just lost your dog. Everything okay?"

"I don't know. Jerry, we have to talk," I said quietly.

"If some woman said those four words to me, I would grab my toothbrush and find a place to hide out. You're not going to get weird on me, are you?" he replied.

"Well, that depends on what weird sounds like to you. I have been fighting with myself all day and losing. I don't like the feeling," I said softly. "I wish I had someone tell me how to behave and what to do about conflicting emotions. This is how high school kids, not grown-ups, or whatever the fuck I am, are supposed to behave. Do you know what I mean?"

"Oh, yeah sure, you're making perfect sense," he said before laughing. "Look, I'm not laughing at you, so please understand that. What I think you're experiencing is second guessing of yourself about the other night. If you had gone out and met some woman, then made out, had sex with her and she spent the night, you would be fine. Your problem originates from the fact that the particular person you spent the night with has a penis and you satisfied them in a way that is a bit unfamiliar to you. The person did have orgasms so you managed yourself very well on that front; you had orgasms as well so obviously you found sex with them exciting, or it wouldn't have happened. Looking at the evening in this simple context, what is the exact cause of the problem you feel? Is it that you opened an unfamiliar door and became frightened by what you saw on the other side? Or something else?"

"You have moments of clarity that amaze me, and your analogies even make sense at times, but I still feel a sense of guilt that's hard to explain," I said.

"That just shows that your mom did a great job raising you. Jewish guilt is a clinical symptom of a much larger problem but one that's correctable."

I laughed and asked, "Okay, genius, how do you correct it?"

He smiled and said, "Usually it involves someone slapping the person across the face and yelling, 'Stop it, you're behaving like a baby! You haven't been hurt so don't act like you have.' Surprisingly that remedy works quite well most times."

We laughed together and I actually felt better by simply laughing with him. "Is this what you would recommend?" I asked.

"No, not this time. Pia is very delicate, so I think she needs more gentle treatment. Take a quick shower, put on the wig and earrings, I'll let you borrow some panties and a loose blouse, and we'll go to the bar for a drink. Let's see how you feel when you get there. In my opinion I think you will feel a lot better with some feminine energy surrounding you."

I was a little reluctant, but I managed to get ready fairly quickly and found myself suddenly rejuvenated by the time we reached the car. Jerry usually brightened my somber moods and I'm glad he was here with me. While driving to the club I didn't feel apprehensive or nervous but nonetheless, Jerry kept the conversation light and made some silly jokes, mostly at my expense but I didn't mind. He looked very nice, not as glamorous as the other night but a pretty, casual chic, and I found myself intrigued knowing that I had him in bed with me a few days ago and that caused me to smile. "I know what you're thinking," he said.

"Fuck you," I replied, "I was thinking about a funny story I heard at work."

"I know that smile so don't try to bullshit me."

We entered the bar and saw a few familiar faces and were greeted with several smiles. The bartender who liked Jerry was there and welcomed him with a kiss and gave me a warm smile and called me by name, certainly not a "Norm" welcome, but I felt better regardless.

After about an hour Jerry leaned over to me and asked, "How are you doing? Feeling better I'll hope."

"Strangely, yes," I replied. "You were right about the energy and everything seems lighter somehow."

"Good. Try to relax, fitting into your new skin is a process but it gets easier as time goes by. There are people who love you for the person you are, and the rest can fuck off."

While Jerry made light of how I felt earlier, he knew exactly what I was talking about when I had gotten home. When we were ready to leave I asked the bartender if he knew Steve, the fellow I was speaking with the other night, and he said he did. I asked him to say hello for me when he comes in and he smiled and said, "Of course."

Refreshed after a few hours of silliness with friendly people, I felt like a new person and told that to Jerry. "You knew how to improve my mood and while I am still confused at least I am in better spirits. You should hang out a shingle," I said.

"Something like 'Psychiatric Help--5₵' I assume," he replied with a laugh. "I learned a long time ago that the type of confusion you're experiencing is directly attributable to your indecision about your sexuality. Now, don't argue just listen for a minute.

"I imagine that you're thinking that you didn't have this type of indecision until you agreed to accompany me to the mixer this past weekend dressed like a woman."

"Jerry, I was not dressed as a woman," I interrupted. "I was wearing nice slacks and a shirt with an androgynous look that you assured me would help me fit in. Did you mean to mislead me?" I replied.

"Phil, may I call you Phil? I did not mislead you; I encouraged you. There's a big difference. I said what I said and to me you looked nice and refined, but you can't tell me that when you looked in the mirror and saw yourself with a pretty wig and hairdo, nice make-up, lovely earrings, lipstick and nail polish, you didn't see yourself as a sexy woman. That's what I saw, and I also saw a very happy person that had the weight of the world lifted from their shoulders.

"And when you looked at me with my make-up wearing a 'come fuck me' dress, who did you see? I would like to believe that you saw a close friend who cares about you, loves you after spending most of their lives with you, but who happens to be wearing a dress and could pass as a woman. Would I be different in jeans and a tee shirt? Of course not.

"You wear androgyny very nicely and I couldn't care if you were wearing jeans and a tee shirt, linen slacks with a blouse and make-up, or nothing at all. But in the club that night, gay men drooled over a beautiful crossdresser and believe it or not, you gave them what they wanted."

I proceeded to park the car and thought for a moment before responding. "You must have planned this for a while by the sound of it," I said. "Why? What inspired you, Jerry? Did I look unhappy? And if I did, how would you understand why? Do you think that the cure for occasional gloom is dressing like a female and having someone stick their cock in your mouth? Or, worse yet, maybe it wasn't about me at all. Were you planning to coax me into bed simply for sex and this was how you did it?"

"That's unfair and you know it. On top of that I felt that I was helping you and I did it because I care about you, just like I cared about you tonight when I suggested we go out for a while in the hope that your mood would improve, which did happen by the way.

"When I asked you to come with me to the party, I wanted you to join me to experience freedom. Freedom from your inhibitions. You know how I dress at home; I never made a secret of my fondness for women's clothing and lingerie and I see the way you look at me sometimes with a certain desire that comes across as you picturing yourself the same way. It's a different look in your eyes and I know it because I've experienced it.

"What I proposed to you was simple and you were given the chance to opt out at any time. Once you agreed to my suggestions and I saw the joy in your eyes, I knew I was right. This is what you wanted, and I gave you the opportunity and excuse that you needed. You have plausible deniability; you were helping a friend, and the outfit was their idea. But you were happy and comfortable as everything came together.

"I have been attracted to you for a long time, but I do not want to jeopardize our friendship with a one-sided romantic involvement. Going to bed with you was spur of the moment and caused me some anxiety but I buried it. I didn't plan to sleep with you that night and if you must know, I hoped to hook up with Charlie the bartender but changed my mind after a couple of drinks. I watched you fitting in so nicely but didn't want something to happen to derail the good vibes of the evening and decided to stick with you in case you needed support. What happened between us happened unexpectedly.

"The guilt that you're feeling now is partly because you have opened a new chapter in your book of life and also because you must make a conscious choice to go back to the bar on your own to be with new friends or wait until another mixer is scheduled in a couple of months when I will prod you to come with me again. If you go back on your own, will you bring Pia or is she something that belongs to the past, a fond memory?"

After a few minutes of silence, I said, "I'm sorry Jerry, I overreacted and said a few things I shouldn't have. I apologize."

"It's okay, I'm glad we got it out in the open. There were too many misunderstandings and it's better this way."

When we got to the apartment, my phone buzzed with a call from Steve and I was taken by surprise. "Hi, Steve," I said. "I just got home."

"Hi, Pia. I stopped at the club and got your message from Charlie," he said. "I hadn't planned on visiting the place this week but since I was so close I figured I would stop by in the hope of running into you. I was just a little late, I see."

"Strange, I wasn't planning on going there tonight either, but Jerry thought it would be nice to get some fresh air and forced me to accompany him into a smokeless smokey bar. It's unfortunate that I missed you," I replied.

"I agree but since tomorrow is Friday and we didn't connect tonight, why don't we meet there tomorrow, go have a burger up the block and get reacquainted?" he said.

"That sounds like a great plan, and I look forward to it. Does 8 o'clock work for you?" I replied.

"Perfect. I'll see you then. Have a pleasant evening," he said and hung up.

"So, hot date tomorrow?" asked Jerry.

"I don't know how hot it will be, but I am meeting Steve for burgers and beer."

"Don't be coy, I heard the softness in your voice and see the twinkle in your eyes. It's really nice and goes to my point about how attractive you are. You spent several hours at the mixer a few days ago and you've got a date already, lucky you," he replied.

"Shit, I need something to wear. As much as I like what I wore last weekend, I can't wear the same thing again right away. And my make-up! I must get it done properly before I see Steve or I will look like a circus clown. Will you be able to help me or should I see if the salon can fit me in? Or should I just go as myself in jeans and a polo shirt without make-up. How does that sound? Don't just sit there, this is all your fault so help me!"

"Do you listen to yourself? I should get you a bag to blow in! Calm down, it's just a date and you never fuck someone on the first date," he said.

"Then how did I wind up in bed with you last weekend? Your memory is so selective. You're telling me to calm down and blow in a bag since nothing serious happens on a first date while forgetting that when we were out last weekend you forced me to give you a blowjob within five minutes of getting home."

"Forced? You took me first even as I struggled to free myself! This bitchy attitude brings bad karma along with it so maybe you will get tied to the bed and fucked senseless on your date with Steve. He might even be an axe murderer! Ever think of that?" Jerry said while trying to hold in a laugh.

"Wait a minute! If we are going somewhere else for dinner I don't know if I am comfortable wearing female attire or even an androgynous looking outfit," I replied. "I would prefer not to be a spectacle for people outside the bar crowd, but I want to look good for Steve. What the fuck, Jerry!

"Oh, I'm sorry," I continued. "Do you want a glass of wine? I'm going to have one in the living room and would enjoy some company for a few minutes."

Without waiting for an answer, I went into the kitchen and grabbed two glasses of wine and went into the living room to sit with Jerry on the sofa. Handing one to him, I said, "Jerry, I feel like I'm living two lives. Since you helped open my eyes last weekend, something that I am very grateful for, I am struggling to decide which of these paths is right for me. You make it look so easy, but I am willing to bet that you faced similar struggles and doubts. Somehow you managed to emerge from the other side a seemingly happy person with a clear vision of the future. How did you do it? How do you still manage it? I need some help because I feel like I am being pulled apart."

"Phil, I think that you are at a crossroads and the choice of direction is complicated by the physical aspects of the decision. You are not troubled so much by the emotional part of how you feel now since you can maintain a level of secrecy in that regard but the physical part requires an outward commitment. You had no real issue with an outfit that presented you as androgynous yet when I said that you looked like a woman, it bothered you even though it was the same outfit. Would you mind looking like a woman when you went outside? Forget what people think but would you feel uncomfortable looking like a young lady while mingling with people on the street?" he said. "I'm guessing that, at this time, you might not."

"Really? You figured this out by yourself just taking into account that you've known me since diapers. My situation is so totally unfamiliar to you I take it and you have no advice to give me?" I said.

"That's not what I said if you paid attention, but I'll try again:

"What I tried to get across to you is that there are two parts to address: the first is the emotional part which I think is the easiest for you from what I've seen. You have adjusted to being with another man, no reluctance on your part or second-guessing yourself. The outward physical aspect is giving you a little bit of a problem. You like soft, feminine things but you don't see yourself as female, you don't fantasize about being a woman, you simply enjoy being with a man and doing what pleases him. Does this sound about right?"

"I can agree with most of what you said," I replied.

"I thought you would. We are a lot alike so I can empathize and right now I think you're feeling a bit overwhelmed. My advice to you is not to play to other people, make yourself feel good first and foremost and remember how you felt when we went out together last weekend. You felt comfortable, relaxed, you didn't feel pressure. You didn't mind being a little risqué and feminine because the environment allowed it. If you go out in the real world, on a date perhaps, what would make you feel comfortable and happy? What about soft clothes, no makeup or very light makeup, maybe clear nail polish and small gold hoop earrings. I believe you will feel comfortable, Steve will see the more natural you with a bit of Pia to remind him of last weekend, and anyone else who sees you will see a handsome young man who enjoys beautiful things. If you are not comfortable then you can modify the troubling part, trial and error. If you opt to go to another drag mixer, take Pia out of the closet. But just remember to make yourself happy and fuck everyone else."

"Thank you, I feel better now. I will try your approach tomorrow night and let you know how it works out and if you're entitled to 5₵. On a separate but somewhat related subject, if I asked you nicely, would you sleep with me tonight?" I asked.

"Do you think that's a wise thing to do in your current emotional state?" he answered.

"Probably not, but you said that I should make myself happy and having you in my bed tonight would make me happy," I said.

"Me too," he replied with a grin.

I finished my wine and while Jerry ordered some Chinese take-out, I went to take a shower. Letting the warm water cascade over my body got the kinks out of my neck and relaxed stiff muscles while providing time to think about the conversation that I had with Jerry. He was right. I didn't have a problem being in bed with him, kissing him and satisfying him orally, all the things that are done between consenting adults in private. I hesitate when it comes to putting on a dress, heels and makeup, and going out on a date. That's too open, too public for now, but perhaps that will change over time but not right now.

My experiences with men are very limited but I am willing to try almost anything and that is more than half the battle as far as I am concerned. He is like a brother to me but that doesn't explain why I find myself drawn to him? Am I frightened to be with a strange man and look for someone safe and familiar instead? It's possible I guess, and maybe between tonight and tomorrow I will have an answer.

I was already in bed when Jerry joined me and tenderly gave me a kiss on the lips. I hugged him and drew him close to me, kissing his neck and working my way down to his nipples. He started moaning as I nibbled on each nipple individually and moved his hands to hold my head tightly while keeping me pressed against his body. As he became more excited he slowly began to roll over to lay on his stomach and placed his arms over his head. I rubbed his neck and shoulders and kissed his back, finally stretching out on top of him, taking his wrists in my hands to stretch him out before placing my knees between his legs to spread them apart.

My penis found its way along the crack of his ass, and I rubbed it into the crease while rubbing my body against his while Jerry moaned quietly in anticipation. I imagined what he must be feeling right now, knowing what's coming, the mixture of pain and pleasure ending with a wondrous release of energy and semen. As Jerry became more excited, so did I. My erection became as hard as granite and once aligned with his anus the slightest forward pressure began slowly pushing it into his body and I watched him close his eyes tightly and grit his teeth. I took my time getting into him and once fully inside I let him rest for a minute while his body became acclimated to the invader that was splitting him open.

Jerry was panting hard when I began to slowly pump in and out, probing the full length of my cock with each thrust. I pushed deep and established a steady pace that brought groans and curses from my dearest friend. "How does that feel? Your ass being ripped apart by another man's cock. Do you enjoy that? Being used like a bitch?" I whispered.

"Fuck you, you'll have your turn one day and I will have you begging for mercy," he replied.

As he finished his reply I began to pump furiously and could feel the muscles in my abdomen begin to spasm and streams of semen were forced into his anus as I cried out in ecstasy. As the pulsing of my cock continued, Jerry had an orgasm and he cried out, cursing me again. I collapsed onto his back and kissed his neck, whispering, "That was fantastic."

I climbed off him and went into the bathroom to wash my cock and brought the washcloth back and proceeded to clean him up before kissing his lips. He kissed me deeply and said, "God, that was wonderful. I'm aching now but in a good way, you hit all the right spots."

We spent the night together, went our separate ways the following day and as good as I felt I found myself thinking about my dinner date with Steve. This would be my first date with another man, and I was nervous. Going out to a drag mixer with Jerry didn't count in my opinion; he is my best and oldest friend and regardless of the sex between us, it was not a proper date per se. There was none of the awkwardness, no probing questions, and we knew each other's history including detailed likes and dislikes. We are close friends and there is an old saying about lovers being friends first, or was that spouses should be friends first? I forget but either way, fucking seems to be preceded by friendship in the best of circumstances.

By noon I was wondering if I was crazy to be going out with Steve at all. We hadn't spent any real time together and as pleasant as he sounds, I have no idea if there will be chemistry between us. I was beginning to understand what women go through and have a new opinion about setups and blind dates. And then there was the issue of what to wear.

I had come to the conclusion that I should abandon the wig and feminine clothes and simply wear something that could go either way, small hoop earrings, and no makeup. Steve saw me as Pia in the club but since I do not usually present as female, I felt that he should see the real me, or very close to it. What if that is not what he is expecting and he is disappointed and decides that he doesn't want to be out with me at all? There seems to be some potential problems on the horizon and I felt that they were adding to the stress. The possible alternative would be going home as usual and letting Jerry fuck me senseless, which might win out in the choice between 'A' and 'B' were it not for the fact that I wanted to see what it would be like to go out with a strange man for the first time.

I was wearing my robe when I came out of the bathroom after a shower when Jerry got home and he walked up to me, opened my robe, and squeezed my nipple as a greeting. "Hmm, a hard nipple so you must be excited for your date," he said with a laugh.

"Nervous and anxious is more like it if you must know," I replied with a smile while pulling my robe closed.

"You could have simply told me that you would like to stay home and we could order pizza," he joked.

"Really? I thought you were planning to go out too," I said.

"Plans change," he replied with a smile. "If you go out, I get to watch you agonize as you get ready and if the date goes well I will get to listen to the sound of wild love-making coming from your room during the night."

"You could have heard those noises if you stayed home too," I said, and we both laughed gently as he understood.

"You're hard to understand, you know. I thought you would be happy to be going out with a nice guy, someone who you seemed to be attracted to only a day or two ago. Someone who you left a message for with the bartender. If you weren't interested, why would you go to so much trouble?" he replied.

"That was wishful thinking, Jerry, this is real," I said as I walked to my room.

Within two minutes, Jerry opened the door and walked in. "Do you want me to tell you what to do? To tell you to stay home with me?" he said quietly.

I thought for a moment then lifted my head to look into his eyes, "Yes, but only if that is how you really feel."

Jerry walked over to me, slipped his hands inside my robe to rub my nipples with his thumbs, then pulled me close to softly kiss my lips. "Pia, don't go out tonight. Let's have an evening together, our first real evening together when we can be honest with each other. I want you to myself and have for quite a while," he said quietly.

"Let me make a phone call while you get some wine to mark the occasion. We have a long night ahead of us," I replied while walking over to retrieve my phone.

Steve was a little upset with the late change of plans, but I knew that he would get over it. Our date had happened quickly after our first meeting and on short notice, so this is one of those times that probably were doomed from the start and could be chalked up to experience. When Jerry returned he found me in bed, naked under the sheet and the happiness was apparent in his eyes. He handed me a glass which I clinked against his and toasted to 'new beginnings'. After taking a sip, Jerry placed his glass on the night table and started to slowly remove his clothes before heading to the shower.

While Jerry showered, I laid in bed, head on the pillow with eyes closed, gently rubbing my nipples as my dick got hard in anticipation. My breathing became heavier as I imagined what would be coming, something that I had prepared for earlier and wanted for a very long time if I was being honest, and tonight was set aside for honesty. I also thought about going out with Jerry the prior weekend, dressed as Pia, draped in soft linen, beautiful makeup, polished nails and a short black pixie cut wig, a lovely female on the surface. Even though Jerry was dressed as a woman as well, I felt comfortable being on his arm while other people watched us together, thinking whatever they wanted. Tonight, I knew I would give myself to him, I would be whoever he wanted me to be, and the thought was liberating.

"You look deep in thought or maybe you're simply drifting off to sleep," he said quietly as he came back to bed.

"I was thinking about last weekend and how I felt when we were in the club together. I realize that I felt free and finally acknowledged to myself that I looked like a lovely female and I knew it all along. I wasn't androgynous even though my hair was short, but I looked like a woman with short hair. I lied to myself just to get to that point, and I have been lying to myself for a long time. I am more feminine than I will readily admit but you saw it in me all along," I confessed.

Jerry kissed me and replied, "And what do you think now? Are you upset with me?"

"No. I am upset with myself for living this long without being honest. You came out years ago and took the consequences alone. I should have done more to support you, particularly since you saw the real me, the person I kept hidden.

"Now I am here in bed with you, feeling liberated because of you and despite myself. I am happy for the first time in longer than I can remember and you ask if I am upset with you. No! I owe you a debt of gratitude and I thank you for opening my eyes."

I pulled him close to me and told him to get under the sheets so I could feel his body on top of mine. I kissed him passionately, opening my mouth so he could gently push his tongue against mine. I slowly began to squirm under his weight and felt his excitement from the contact of our flesh. Jerry kissed my neck and I wrapped my arms around his back and began to gently scratch his skin, whispering, "I want to feel you inside me. I want to feel the pain when you enter me and the pulsing of your erection as you orgasm. Don't be gentle, I don't deserve it nor do I want it. Fuck me like the bitch I am and don't stop."

Jerry put his arms under my knees and lifted them to rest over his shoulders as he leaned into me, the head of his cock against my anus. I kissed him hard on the mouth as he slowly pushed his hard cock into my ass as I grimaced and grit my teeth. "How do you like it, bitch?" he said. "Not as much fun when you're on the bottom, is it?"

"Fuck you, cunt!" I replied.

Jerry pushed hard and began to slam his hips into my butt cheeks rapidly as he pumped vigorously, obviously intent on hurting me as I demanded. I cursed him and threatened him, but nothing had an effect on him other than to make him more aggressive in his actions.

After several minutes I felt him push as deep as he could and then hold still as his cock pulsed what I imagined was a river of hot semen into my ass. I held him tightly and panted until my strength ebbed, my muscles relaxing into a pile of flesh on the bed. I nibbled his ear and managed to whisper, "Is that all you've got?" before laughing. "God, I'm a mess. My muscles are twitching, and I have no strength. I am so sore and ache everywhere, joints that I didn't realize existed, now hurt."

"Yeah, that was amazing," he said panting. "But you're okay?" he asked.

"More than okay," I said, "I've never felt better."

We stretched out and hugged, I put my arm over his chest and placed my head on his upper arm. "Do you realize that you took my cherry, that I'm no longer a 'virgin'?" I said.

"Wow! That was a big step. You know what people say: Once you let another man fuck your ass, you're officially a sissy and cannot go back to what you were before. So, to be clear, as of now Phil doesn't exist anymore. You're officially Pia whether you're wearing a wig or a dress or your regular street clothes. Even if no one sees that side of you and uses your other name, you will know it and I will know it." He reached his hand down to trace the crack of my ass to my legs and came back with some of his cum on his fingers to show me. "This will mark you forever, Pia."

"I know. You are my first and I wouldn't change a thing," I replied and snuggled closer to him.