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Progress Dirty Rachel (c) 2019 Earlier this year I got a call from an old friend, Tom Houston. Ten years ago Tom and I had been drinking buddies at our alma mater, UNC Chapel Hill. He had gone on to law school, while I had gone on to Bartending School... a 2.0 GPA like mine made options like that seem reasonable. I hadn't seen Tom for a year or so, so I was surprised to hear from him. He was even more surprised when I told him my news: For the past six months, I had been living full time as a woman. "Are you still there, Tom?" I asked after dropping my bombshell. "Yeah, Jim. I don't know what to say." "Actually, it's Jill, now, and you don't have to say anything." "After all the women we chased together..." "Yeah, we did. If it's any help to you, I still like women." "Oh, Jesus. You're trying to drive me crazy." "Not a very long drive, you have to admit." "Yeah I know. Hey, dude, let's get together for a beer this evening." "It's not dude anymore, dude." "Sorry." "Maybe you're right about getting a beer. You won't call me dude anymore after you see me." "Okay. How about The Office?" The Office was a semi-sleazy bar about halfway between my apartment and Tom's law office. It had a pool table, an old pinball machine and cheap beer. The characters who hung out there ranged from the alcoholic businessman who drank until he fell off his stool every night, to the fearsome looking biker with a heart of gold, or the bookie with a wooden leg who ran his business on The Office's phone. And, of course, me, the anti-social transsexual chick. I dressed quickly, pulling on tight jeans and a baggy UNC sweatshirt. I wore the sweatshirt because I didn't want Tom to be distracted by my boobs, which, after the implants, were on the large side. Oh, hell, in reality, they're pretty fucking huge. I don't know what I was thinking when I asked the doctor for them. They're traffic-stopping big. My jeans were tight because all my jeans are tight. I got butt implants to match the breast implants, and I now have twin hemispheres on my ass. Being all T&A has its benefits, but it also has its drawbacks. I make killer tips as a bartender, but I get some unbelievably foul propositions. However, I haven't taken anyone up on their propositions. As a matter of fact, I haven't even been out on a date. I didn't want to have to explain the anomaly between my shapely thighs. You see, my transition is incomplete. I have been on hormones for nine months. I've had the implants and facial feminization surgery, but sex reassignment surgery, the operation to give me a vagina, would be six months or more in the future. In the meantime, my penis and testicles have shrunk because of the hormones, and without Viagra, I can't get an erection. Again, there are benefits and drawbacks: less bulge in my panties, but it's getting more and more difficult to orgasm when I masturbate. I slipped into some pink sneakers, pulled my long blonde hair back into a ponytail, and I set off on foot for The Office, bouncing and jiggling all the way there. When I arrived and got Tom to close his gaping mouth, we eventually slid into opposite sides of a booth and ordered draft beers. Tom's first words were, "Tell me why." "Why, what?" "Why have you become a woman?" "The simple answer is that I've always been female." I cleared my throat. I've explained this two dozen times to family, friends and therapists, but it still wasn't easy. "I've always been gender dysphoric, even as a child. I'm finally making my outside congruent with my insides." "You were a pretty manly guy in college. How'd you pull that off?" "I worked hard at it. And I cultivated denial. I drank too much to kill the pain. When all else failed, I had a stash of female clothes, and I dressed up privately for relief. But I was desperately unhappy and ashamed." "Are you happier now?" "Yeah. I've still got issues, though, so I'm still seeing a therapist. But, you know, baby steps." "You look amazing." "So do you, Tom." And he did. "You working out?" "A little." He looked sheepish. "Very buff shoulders and lats, dude." "Your voice. How do you do that female voice?" "When you heard me on the phone, did I sound female?" "No, you sounded like you." "You just hear a difference because you see me. There isn't a big difference between a tenor and an alto, really." "Wow. You're the complete package." "Almost. I still have one surgery to go. The big one." He shuddered. "Oh, come on. It's not that bad." "Jesus." "There's the difference between us, in a nutshell. I want mine internal, and you want yours external." I laughed. "Do I look like I need a penis?" "Don't ask me that, Jill." "Oh, sorry. You mean you'd offer me yours for twenty minutes or so?" "I mean... Well, yeah. Um. You look..." "Fuckable?" "Eminently," he said quietly. "Thank you." "You... uh... gettin' any?" "No. You?" "Not much. Rachel moved back to New Jersey." It got a little quiet after that, so I suggested that we play pool. I had always been able to beat the crap out of Tom at pool. In the mirror behind the bar, I saw Tom staring at my ass in a not entirely platonic way. One might think I'd be repulsed or offended. I would have thought so, too. But, much to my surprise, I found myself being flattered. I wiggled my ass a little for him and watched his reaction. He pursed his lips and whistled silently. I shivered a little myself as I realized I felt more aroused than flattered. "See something you like, Cowboy?" I asked him, looking in the mirror. "Yeah, wow. Sorry to stare." "It's okay. I get that a lot." "I can see why." After a few rounds of pool we decided to call it a night. We left the bar, got into his Porsche and he drove to my apartment, actually half a house in the old Brooklyn neighborhood. He came around to open my door. I took his elbow as we made our way up the path to the big front porch. Anyone seeing us walking toward my door in the dying light of the spring day would have naturally assumed we were lovers, or would shortly be lovers. At that moment, neither Tom nor I knew what would happen, or even what we wanted to happen. Could he get past my non- standard plumbing? Could I? I had fantasized about sex with men, of course. In some of these fantasies I was worshiped, in others I was used. Sometimes I was a princess, or a high-priced call girl, or a trailer park slut, or a bukkake target. I particularly liked the bukkake one, and I frequently imagined myself covered in the jism from dozens of cocks. That was the thing; these fantasies were generally about cocks, not about the men attached to the cocks. If I was to be completely honest, I'd have to admit that I've practiced with vibrators and dildos so as to be ready if the opportunity presented itself. But I didn't think I wanted to be that honest right now. While the idea of taking cocks into my orifices was exciting, the idea of making love to a man, kissing him, or even just holding him in my arms made me uncomfortable. Nauseous, actually. Upon reflection, I had decided that I wasn't ready for an actual relationship yet. When I was ready, I'd know it. Or I'd be a lesbian. That would be okay, too. So I knew that sooner or later I'd be faced with the prospect of an intimate relationship with an actual flesh and blood man. That moment had now come, and I would have to make a decision about what I would do. Tom was a nice guy, an old friend. He had been understanding of my peculiar situation. He was a handsome, muscular man, with really great shoulders. Great shoulders. And biceps. I ran my hand up his arm just to make sure. Yeah, great biceps. Really great. I unlocked the door and ushered him in, closing it behind us. I steered us towards the living room. "Want a glass of wine? Coffee?" "Not right now. Can I ask you something?" "Anything." I stood in front of him, looking up into his eyes. "Would you mind if I kissed you?" Steeling my resolve, I whispered, "I would be devastated if you didn't." So he kissed me, gently at first, then more insistently. I opened my mouth to accept his tongue. Our tongues wrestled for a few minutes, and to my surprise, I became increasingly weak in the knees. When I couldn't take any more, I broke it off, breathlessly. "Wow," I said. "I've never kissed a man before. How did I do?" "The best. You are unbelievably sexy." His hand drifted down my back to my ass. He cupped it gently and squeezed. "Come here," I instructed, and I led him to the couch and pushed him down into a sitting position. I turned and walked into the kitchen. I was shaking with excitement. I realized it wouldn't take much to make me cum in my panties. I got us two glasses of white wine and returned to the living room. Tom was sitting on the couch flushed with lust, trying to hide an obvious erection. That was it, I was undone. I set the wine glasses down. "You don't mind if I take off this sweatshirt, do you? It's hot in here." He said something unintelligible, not taking his eyes off me. I lifted the hem of the shirt and lifted it up, revealing my breasts in a black satin bra. I lifted it off over my head. He seemed to like my boobs, and why not? They're awesome. I dropped to my knees in front of him, spreading his legs with my hands. His erection tented his pants impressively. Looking him in the eyes, I ran my hands up his inner thighs until I got to his crotch. I took the tent between my palms and smiled at him. "May I see it?" He seemed incapable of speech, but he nodded. I unzipped his Dockers and withdrew his penis. It was surprisingly large, and it was gorgeous... perfect, actually. I kissed it lightly on the tip. He moaned. "I've never done this before, but I'd really like to try. Would you mind very much if I sucked your cock?" "I'd be devastated if you didn't," he whispered back. I began by kissing it again, then licking the head. A bead of pre-cum oozed out, and I licked it off. Then I slowly took the head into my mouth. This was even better than I had imagined it would be. I took a deep breath through my nose, then slowly, deliberately began taking the whole thing into my mouth, then into my throat, until my lips were up against his neatly trimmed pubes. "Oh, my God!" he said. I raised my head until only the head was in my mouth. Twice more I took his cock into my throat before he grabbed my head, holding my face against his pubic bone while he ejaculated down my throat. It wasn't the kind of sweet, gentle caress I was expecting, but nice, in a somewhat brutal, abusive way. I was relieved when he let me come up for air. It was like I had imagined it would be, sort of. It felt and tasted like I had imagined it would. It was as rewarding and exciting as I had imagined. On the other hand, the blowjobs I gave in my fantasies lasted more than twenty seconds. Starting off with more delicate sucking and licking before getting to the deep throat part would probably prolong the experience, I thought. Before I started, if I had a fear, it would have been that I'd be unable to get him off in a reasonable amount of time, not that he'd come too soon. But I thought that with practice I could learn to be an excellent cocksucker. No, fellatrix. That's better. I'd be an excellent fellatrix. I looked up at Tom. "How was I?" "God, Jill. That was the best blowjob I've ever gotten. By far." "Not too quick?" "I couldn't help it. It was just so good." "I'm glad you enjoyed it. I enjoyed it, too." "That can't have been your first." "I swear to you." "Wow. You're a natural." "I feel like I really need more practice to be as good as I can be. Would you let me practice on you again some time?" "When did you have in mind?" "How about, let's see, it's 8:30 now, how about 8:30?" I kissed it, and it jumped. I didn't wait for his answer. I began by teasing and nibbling it, then licking and sucking gently. He got hard immediately. Then I began bobbing up and down on it without taking it in my throat. I fondled his balls lightly. I looked up at him. His eyes were closed and his mouth was open slightly. I worked on him for about five minutes before I began to deep throat him. Again, it only took a few strokes before he was on the brink, and again, he grabbed my head and shoved my face into his crotch while he unloaded his jism down my throat. I moved to the couch and snuggled against him. He put his big arm with the great bicep around my shoulder. I rested my head on his muscular shoulder, feeling very womanly, very sexy, and very proud of myself. Also, incidentally, painfully aroused. Tom, recovering from his sexual high, seemed to be thinking about what had just occurred. I thought I could read his thoughts. He had just allowed a man, or a former man, to blow him. Twice. And he had enjoyed it. I understood why he might feel a little uncomfortable and in need of reflection. He said it was getting late and he had to work in the morning. He extricated his arm, still with the great bicep, from under my head and stood up. Not only did I understand, but I also wanted him to leave. I desperately needed to relieve my own needs. "That's okay, Tom, I understand. I enjoyed our little visit." "So did I, Jill." He paused. "I'll call you." "That would be nice. We could have dinner or something." When I was a man, I told lots of women that I'd call them when I had no intention of calling them. If he wanted to call me, I wanted him to call me. If what had just transpired had scared him, I didn't want to force the issue. And I didn't want him to think that I thought him obligated by what had happened to do something, or anything. I certainly didn't want him to think that I expected us to be going steady or something. "If you feel like it," I added. I don't know the etiquette of these things, or more appropriately, I had just never thought about it before. I suppose that other women, women with more experience with these things, have thought about it. But it seemed bad manners right now to even allow him to taste his own cum, let alone try to feed some back to him, so I rinsed my mouth thoroughly with wine before kissing Tom goodnight. After he left, I took a Viagra. Twenty minutes later, as I was lying on my bed with my jeans around my ankles, yanking on my cock, I thought about what I had just done, about what his cock felt like in my mouth. I had enjoyed it more than anything I had ever done, I thought. Yes, I loved being a fellatrix, a cum swallowing cocksucker, and I looked forward to doing it again and again, to Tom and others. Many others. I kicked off my jeans and panties and bent double on the bed so that my cock was directly above my mouth. Pulling on my hips, I could just barely touch the end of it with my tongue. I came in my mouth and on my face. Yes, I did. It was lovely, thank you very much. I swept up a blob of cum with my finger and licked it off. I smiled. The next day, a dozen red roses arrived with a card from Tom. He called that afternoon and we made a date for my next night off. Dinner and a movie. Maybe I'll give him head in the theater, or in the car, I thought. Maybe I'll let him fuck me. Maybe not. At work the next night, I felt more confident, sexier. I felt like I had more swing in my walk, and when a customer looked down my shirt, instead of moving away and turning my back, I looked him in the eye and smiled. (He left me a fifty.) I found myself daydreaming about one of my co-workers, a big, muscular college student with an obvious bulge. This was something I had never done. I had never fantasized about a real, live man, especially one right next to me, one that grazed my ass as he passed behind me, one whose cock was within my reach for hours on end. And when I got home and took a Viagra, I let the fantasy play out while I masturbated with my dildo up my ass, imagining him fucking me. I had evidently broken through some psychological barrier. At my regular appointment that week, I told my therapist about it. She asked how I felt about my daydreams. "Well, they're enjoyable. They make me aroused." "And you find this arousal enjoyable?" "Yes. Well, I mean, it's inappropriate to be thinking about a co- worker's cock when I'm supposed to be thinking about mixing drinks and taking care of the customers... But the arousal is pleasurable. Even if I feel a little guilty." She sat for a long moment without saying anything. "This behavior and the feelings about the behavior are both very common among women. I'd go so far as to call them normal." She paused again. "You're making real progress toward womanhood, Jill. I'm proud of you. Soon, I'll bet you have a real sexual encounter with a real man and..." "Oh, I forgot to tell you. I've done that." "Really!" "I met up with an old college friend, took him to my place and gave him a blowjob. I really enjoyed it, and so did he." "Was it like a date?" "More like a hook-up." "Has he called you?" "Yes...And sent me roses." "You go, girl." That affirmation from my therapist opened the floodgates. "He did something I didn't like." "Oh?" "He held my head down on his dick. I mean, while I had it down my throat, he forced me to keep it there." I waited. She waited. "Do men... Should I expect that? Is that a thing they do?" She took a few seconds to gather her thoughts, then she smiled. "Under other circumstances, if you were fifteen and giving your first blow job, you would probably check in with your girlfriends about this kind of thing. As you know, there is a wide variety of behaviors that fall under the broad umbrella of what is 'normal'." She paused. "Non- consensual actions are not okay, ever. But some women, under some circumstances, might find having their heads held down like that arousing. But if you don't, you can tell him no." "I never did that. I would never have forced a woman to do anything." "And you shouldn't, of course." She shifted in her seat and cleared her throat. "Down your throat, you say? You were deep throating him?" "Uh-huh." "The first time...I've got to say I'm impressed. Wait... that may have been unprofessional and inappropriate. I shouldn't..." "Don't worry about it. I have a dildo I practice on." She shifted in her seat again. "I see," she said. "Well, if you don't like it, you could tell him no." "I don't want to stop sucking his dick, just have him stop pushing my head down." "Tell him that." She looked at her watch. "Is our time up?" "I'm afraid so. Are you okay?" "Yeah. If this is the biggest problem I have, I'm in pretty good shape." She laughed, and said, "Yes, you are. You really are." And, you know, I am. I spent every available minute that week thinking about my date with Tom on Friday; what I would wear, what I would do, what I would say. I wondered if I should bring up our tryst, or whether he would, or whether it would be an elephant in the room. I wondered if he had thought about it, whether he regretted it. I imagined him masturbating thinking about it and also imagined him telling me it could never happen again. The more I dwelt on the questions, the more worried I became. "Frantic" might be the right word. It seemed to me that I had two choices. Either I could be passive and submissive, allowing him to drive the relationship, or I could take the wheel and drive. I was still learning what it meant to be a woman, who I was as a woman. I wasn't interested in going through all the hormones and the surgery and the fear and the uncertainty just to be told by some man what I would be allowed to do. I was still thinking about this as I walked to work that night. The scale of masculine to feminine was a whole different continuum from the dominance to submission continuum. This was a revelation to me, although I wasn't sure why. I hadn't been living my life so far as a shrinking violet; what I had already done to reinvent myself took courage, or for lack of a better word, balls. I was literally and figuratively a woman with balls. I smiled. I had known and admired assertive women in my life, women who didn't take any crap, women who weren't shy about telling people what they wanted. I stood a little straighter as I waited to cross the street, my shoulders back, my tits thrust forward. I'm kind of a badass, I thought. Out of nowhere came a brief vision of myself in a leather cat suit and a riding crop. Maybe not that much of a badass... but maybe so. I walked into the restaurant with a big grin on my face. I have mentioned my big, muscular, young coworker already, and I have mentioned my fantasies about him and my arousal...and, well, these, let's call them daydreams, they reasserted themselves when I saw him. I found myself smiling, and without really meaning to, I turned a fairly high wattage smile on him. It had an immediate effect. Within seconds he was trying to hide a substantial boner. Wow. Here, in actual blood- engorged flesh, was evidence of the power I could wield over men. If a smile could do that... my goodness, the possibilities were mind boggling. He was trying to turn his lower body away from me to hide his arousal without losing sight of the smile. It was adorable. I inspected my mind; it was boggled. "Follow me," I whispered, and headed for the back bar area. Looking both ways, I grabbed his hand and ducked into the stock room and closed the door. "I'm not..." he stammered. "Shhh," I replied. I reached for his crotch and grabbed his cock through his pants. "I don't think..." I put my hand over his mouth. "That's right. You don't think. I think. You shut the fuck up." He nodded meekly. I dropped to my knees and pulled down his zipper. It was a nice cock, long and thinner than Tom's. I thought it would go down my throat nicely, and in actual fact, it did. I didn't waste any time with preliminaries. I got straight to the best cock sucking and throat fucking I knew how to do. I wanted this to be quick, and I was not disappointed. It wasn't as fast as Tom's first time, but in just a few minutes he whispered, "If you don't want me to cum in your mouth, you should stop." "Didn't I tell you to shut the fuck up? Cum, already," I whispered back, and I got back to it. He did, copiously. Much more volume and force than Tom. Youth, I thought. As I got to my feet and dusted off my knees, I whispered to him, "You will be absolutely silent about what just happened. Do you understand? Nod if you understand." He nodded. "Not a fucking word." He nodded again. "Wait two minutes before you come out. And wipe that shit eating grin off your face." For the record, he was unsuccessful in wiping off the grin. I scowled at him, but that didn't help. We can discuss and debate issues of dominance and submission and feminism and bad-assery and balls and all the rest of that shit. I could hold forth for a half hour psychoanalyzing my motivations, and his and what it all meant. Who really had the power when I was on my knees with his dick in my mouth? I had about 30 psychology credits and five years of therapy, including a couple of years with a Jungian. So I could explain the fuck out of it. But I don't think all that would get me any closer to the heart of the matter than I was at the start. But what I could tell myself without fear of internal contradiction was that it was a really slutty thing to do. I had emerged from my chrysalis as a cock sucking slut, and I wasn't sure how I felt about that. On the one hand, it was a one-time thing, a moment of weakness, a slip, a passing fancy. It was a meaningless encounter with no lasting consequences. On the other hand, I really, really enjoyed it, and that made it fraught with meaning. I liked being a badass bitch using a man for my own gratification, and I liked sucking cocks. What was my future likely to be like when I got my penis turned into a vagina? Would I spend all my time on my back? Would I cuckold my future husband with the gardener and the pool boy and his law partners and the kid who delivered the pizza? Fraught with meaning and portent, I tell you. I would have to wait and see how all that played out. Earlier in my sexual career, when I was struggling to maintain a masculine facade, I learned that my need to acknowledge my femininity by crossdressing ebbed and flowed. My needs would build over time until the need to put on a pair of panties became an irresistible compulsion. It was as if I went into heat. All my sexual energy, fantasies and desire were channeled into creating some facsimile of womanhood, and jerking off in various embarrassing ways. When I was overcome by one of these episodes of heat, I did all kinds of things. I wore lacy black bikini panties, black stockings and garter belt under my jeans to my graduation. I was very close to adding a butt plug, but I resisted. I did wear a butt plug on a drive to Florida for spring break in my junior year. The point of this is that I expected my sluttiness to manifest itself in cycles, like my crossdressing had earlier. I expected it to become a compulsion that I would be almost powerless to resist. How I reacted, and what humiliating or risky or self-destructive actions I would take remained to be seen. The gardener and the law partner might be the least of it. I reflected and analyzed in an intellectually detached, self-aware way until the next night at work, when I immediately took my victim into the stock room again. After blowing him, threatening him, and swearing him to secrecy again, I emerged back into the bar with the same feelings of pride and power as I'd had the earlier night. Intellectual detachment be damned. I wanted to own my sluttiness and my prowess as a fellatrix. (I do like that word.) Life was good, for about a minute and a half. Then the intercom phone rang. "This is Jill." "Jill, could you step into my office for a few minutes, please." It was Harry, the owner, an old, fat, kind of gross married guy who looked too long at my assets and made me uncomfortable every time I was near him. I knocked on his office door and he told me to come in. "Please close and lock the door," he said. Oh, shit. "What can I do for you, sir?" "Well, we can discuss that. Are you aware that we have a security camera in the stockroom?" Obviously not, you moron. "No, sir." "Would you like to watch yourself in a video from just a couple of minutes ago?" I shook my head no. "Are you sure? It's a very impressive performance." "No, thank you, sir." I suspected that I knew where this was going to end up, with me fired or on my knees in front of him. I'd suck his dick, if it came to it. I didn't want to lose my job, but a blowjob would be the end of it, or I'd quit. I came to that conclusion instantly, and I approached what was to come with relative equanimity, considering. My experience with giving head was severely limited, but so far, it was not unpleasant. I understood that a vindictive, lecherous, fat, old man could probably make it unpleasant, if he wanted to. But I had options, too, up to and including screaming rape or punching him in the nuts. Or biting his dick off. Again, this was probably one more experience I missed out on by never having been a teenaged girl. So, I thought, "Bring it, fat boy." Outwardly, I smiled sweetly. Inwardly, I pulled up my armored bitch panties, so to speak. "Am I fired?" "Well, I haven't decided. I would have to have more information." He raised his eyebrows and smiled in a distinctly unpleasant way. I waited. "The picture in the video is unclear. You know how CCTV is. I couldn't tell exactly what you were doing." That was a novel approach, I thought. Purely a fact-finding exercise. "I gave him a blowjob," I said. "Blowjob? What is a blowjob?" Oh, you creep. "I was fellating him, sucking his dick, performing oral sex on him." "I'm surprised. I was under the impression that crimes against nature were felonies in North Carolina." "I guess," I said. I wasn't expecting that. "I'm wondering if I have an obligation to call the police." "Oh, for God's sake, shut the fuck up and whip it out. I'll suck it, and neither of us will ever mention this again." I moved quickly to a position between his knees. He started extracting it from his pants, and continued extracting it, and continued extracting it, and he finally had the whole thing out and laying across his fat thigh. There, right in front of me was a firehose of a penis, easily ten inches long, and not fully erect. And fat, oh, my God, it was fat. My jaw started hurting just looking at it. I needed to either suck it or quit, I thought. So I got busy. I didn't think there was any chance of getting that thing down my throat. It would have to be a hybrid hand job/blowjob. I got both hands around it. It was huge, and it hardened impressively. I was kind of expecting a soft erection, age, you know. But no, it was back-seat- after-the-senior-prom hard. Very impressive. I took the head into my mouth, while stroking the rest of it. A thought, a feeling, really, came into my head: as much as I hated to admit it; I loved this cock, and I was going to love trying to get him off, trying to force it down my throat, if I could. You slut, I said to myself. You dirty girl. I got to work, gently and hesitantly at first, then with some more suction and more vigorous stroking. I began to get my throat lined up with the monster. I got it all the way back in my mouth, took a deep breath through my nose, steeled myself and pushed. Voila! It slid past my epiglottis with a kind of pop. I took another inch or two, and he groaned. I pulled back off of it, and I took a couple of deep breaths, then I went back to trying to get that thing down my throat. Now it was a challenge, a matter of pride. Once you get past the epiglottis, length isn't really much of an issue, in my limited experience. I'll be able to do this, I thought. And, indeed I was. It was thrilling, exciting, arousing, and wild. I was deep throating the biggest cock in three counties, and I was loving it. I took it all the way down my throat, until my lips were in his pubes. Then off, then on again, then off, then on again. I built up a rhythm, gradually getting faster, up and down. I caught a breath every other stroke or so, which made it a sustainable routine. I found it hypnotic. All my concentration was wrapped up in being a cock sucking slut. Oh, my. He lasted a couple of minutes, then he shot cum directly into my stomach with a groan. I came very close to cumming myself. It was one of the most exciting events of my life. It was as if I had just won the Masters, or the World Series. Almost regretfully, I freed it from my mouth, and kissed it goodbye. "Well?" I asked. "Well, what?" he panted. "Are we even?" "More than even. That was unbelievable." "Thank you." "No," he said, "Thank you! How'd you learn to do that?" "Everybody needs a hobby." "I'm going to start calling you Holly Hobby." "And I'm going to start calling you Seabiscuit. Are we done here?" "Unless you want to give it another go." "Maybe another time. I enjoyed it," I admitted. How much of this would I recount to my shrink? She had seemed kind of uncomfortable, especially in the lower parts, when I had told her about my earlier exploits with Tom. It hardly seemed appropriate to get your shrink so turned on that she had to diddle herself before the end of the hour. Maybe I was projecting, I thought. I laughed. The next evening, Tom took me to dinner at a casual dinner house. I was overdressed. The crowd was mostly in jeans and shorts, and I wore a little black dress with a low, scoop neckline that showed more of my boobs than was appropriate. (Funny how the same dress is appropriate at a more formal place and looks slutty at a casual place. I don't understand that at all, but there it is.) It was okay. I got some shitty side eye looks from some of the women present, but some leers from the men. I put some extra swing in my walk as I preceded Tom to the booth. Tom, ever the gentleman, tried hard not to look down my dress as we slid into seats facing each other. Every time I caught him sneaking a look at my boobs, I smiled at him. After several surreptitious peeks, I leaned across the table and whispered, "They're pretty awesome, aren't they?" "What?" "My tits. You seem to like looking at them." "Sorry, yeah, they're amazing." "Thanks. You can play with them later, if you want." "Oh, my God." "You could cop a feel right now, if you wanted. I don't care what anyone thinks." He laughed. "I think I can wait." "If you're sure. They're right here if you change your mind." I smiled innocently. "I'll bet you have an erection already." "You'd win that bet." He shifted in his seat. "I could come over to that side and give you a hand job, if you like. Or I could go under the table and give you a blowjob.? I smiled sweetly. He swallowed with some difficulty. ?Or we can wait until after dinner.? I shrugged, which made my boobs jiggle. He saw the jiggle and gave a little involuntary shiver. ?We can talk about the weather. It's hot, don't you think?? ?Oh, it's hot all right.? ?That's what I thought you'd say.? I picked up my menu and looked it over quickly. ?I know what I want. Do you know what you want?? ?You're killing me here, Jill.? ?A little flirtatious banter won't hurt you at all, drama queen.? ?Okay. Flirtatious banter. Right.? I had discovered that I enjoyed turning men into jelly, but I didn't need to work this hard to turn Tom into jelly. He was, from our first encounter on, jelly-adjacent, let's say. He looked at me like a starving man eyes an Oreo, all the time. He was smitten, which was a good thing, but it carried with it some responsibility on my part, it seemed to me. I wasn't into sadism, (as far as I knew?time would tell) so I really didn't want him injured by my flirtatious banter, otherwise known as cock teasing. I crooked a finger at him to get him to lean over the table so I could whisper in his ear. ?I just want you to know that you're going to have all the orgasms you can stand tonight. I don't want you having blue balls and making you uncomfortable. I'm just playing with my food before I eat it. Okay?? Tom laughed out loud. ?Sure. I'm patient.? And he was. I stopped trying to make him cum in his pants before we were done with dinner, but I never let him forget what was in his near future. It was a nice dinner, the company, not necessarily the food, which was mediocre. But we had fun and we flirted, and when it came time to leave, we left with our arms around each other, like boyfriend and girlfriend. It was nice that we were able to be comfortable with each other, and that I didn't have to analyze and overthink every word either of us said. It was our first real date, and for a first date, it went spectacularly well. And we hadn't even gotten to the sex part yet. We went to his place, which was much nicer than my place. It had framed pictures on the wall and modern, expensive looking furniture. The couch looked like it would be just right for him to bend me over the back of and screw the daylights out of me. Of course, the kitchen island looked like a good place to fuck, too, and the rug, and the stairs. Everywhere I looked, there was another place custom made for having sex with this guy. I was sure that nobody else would see this apartment as a fucking and sucking Xanadu. But what if they did? Did other women, more experienced women, survey a room for likely locales for sex? Had other women gotten what they wanted in this room, or the kitchen, or the bedroom? How much thought had Tom put into creating a seductive pussy trap? I hadn't even been upstairs yet. Maybe his bedroom had a sex swing and spanking horse in it? What if his bed had wrist and ankle cuffs attached to the corners? Would that be a good thing or a bad thing? I wasn't sure. Years ago, I had experimented with bondage, with one woman in particular. In these scenes, with one exception, she was the one being tied up. She enjoyed pain and humiliation and being helpless... really enjoyed it. She had orgasms from spanking and from tit torture. She bought a flogger for me to use on her. The sole exception was the time she convinced me to dress as a woman (no, it didn't take much convincing, but I pretended to be reluctant.) She brought an absurdly large strap-on to use on me, but I sent her out to buy a more human sized dildo and the party size bottle of lube. The scene played out in predictable ways, some pleasurable, some not. As I reminisced, I realized that my resistance to having my head held while sucking cock might date to this episode, when she tied me up on my knees and fucked my face brutally while holding my head. But I looked very hot in the French Maid costume she bought for me. I must have been staring off into space while all these thoughts went through my head, because he touched my shoulder and asked if I was all right. ?Oh, yeah, sorry,? I mumbled. ?I was lost in thought.? ?Anything you want to share with me?? I laughed, a silvery, tinkling sound that even I found seductive, and which I had practiced with the voice recorder on my phone for many hours. ?Not right now. Maybe later.? I turned my back to him and rubbed my ass against his crotch. ?Will you unzip me, please?? He unzipped my dress slowly. I could hear his breathing getting ragged. Under the dress I was wearing only a thong. I stepped out of the dress and dropped it on the couch. I heard a swift intake of breath as I turned around to face him. I took his hands and placed them on my breasts. ?As promised,? I whispered, smiling. I should note that my boobs not only looked incredible, they felt very realistic. The breast tissue has grown considerably, even after having the silicone gel implants installed, and my areolae are large, especially for a trans woman. My nipples were currently erect. Hell, my nipples get erect with very little provocation, and the high beams had been on through most of dinner. They were also surprisingly sensitive. I love having my boobs touched, and it seemed that Tom enjoyed touching them about as much as I enjoyed having them touched. He kneaded them, cupped them, lifted them, and squashed them, while I smiled. He bent over and took my left nipple into his mouth. I gasped. He moved to the right one. He licked, flicked and sucked expertly. I let him continue for maybe fifteen minutes. I had the feeling he might have gone on all evening. ?Take your clothes off,? I whispered in his ear, and stuck my tongue in it. That diverted his attention. He took off his shirt. I rubbed my hands over his chest, those big, hard pecs, and his abs. He was even more beautifully muscular naked than he was clothed, and as I've already noted, he looked and felt wonderful with his shirt on. I watched entranced as he undid his belt and dropped his trousers. He was wearing black bikini briefs. I had never seen a man wearing bikini briefs before. They weren't really much different from my bikini panties, but rather than looking girly, they looked very manly, very sexy. They framed his package nicely and showed off his ass. ?I love your man panties,? I said, grinning. I grabbed his crotch. ?I hoped you would. They're brand new. You're so sexy that I felt like I should try to keep up.? I pulled them down enough to take his cock out of the waistband. I held it like I would a screwdriver, or a flashlight. It hardened to fully erect instantly upon being freed from the panties. With my other hand I grabbed a handful of butt. He followed my lead, grabbing my ass with both hands. I began jerking his cock, and he surprised me by ejaculating all over my belly. ?I'm sorry,? he said. ?For what? Being turned on?? ?For cumming so quickly.? ?It's flattering. Never apologize for cumming on me, or in me, or because of me. Tell me,? I asked, never letting go of his cock, ?have you been jerking off thinking about me?? ?Yeah. Three or four times a day. On Tuesday, I jerked off at my desk.? ?That's hot. What were you fantasizing about?? ?You sucking my cock.? ?Where?? ?Under my desk.? ?That's hot. Was I naked under there?? ?No, fully clothed.? He was panting already. ?Did you cum in my mouth, or on my face, or what?? ?On your chest.? ?So I had to leave your office wearing your cum all over me.? ?Yes. Is that too weird?? ?Not at all. I'd totally do that.? ?How about on your face?? ?Do you want to cum on my face?? ?Do you want me to?? ?Yes.? I sat down on the couch. ?Cum on my face, stud. I want to watch you jerk off on my face. Come on, do it.? It didn't take long. Cum splattered on my forehead, and my cheek, and my chin, and dripped down onto my tits. ?How do I look?? ?Beautiful.? ?And slutty?? ?Yeah.? I laughed the practiced laugh again. ?That's the look I was going for.? We sat on the couch together, our arms around each other. I scraped some of his cum off my cheek into my mouth. ?Yummy.? He moved in for a kiss. I didn't stop him. After the kiss I asked, ?How do you feel about kissing me with your cum in my mouth.? ?It's not bad at all. I don't know that I'd call it yummy, but it's not going to keep me from kissing you.? ?My man!? I kissed him, hard. I got him off twice more that night. At our therapy session, I recounted a sanitized version of the week, leaving out the encounter with Seabiscuit entirely. I thought it best to skip over that. I mean, I did act assertively to protect my interests. But I traded sex for my job, acquiesced to blackmail and so on, which I thought would bother her. And if I told her how big his dick was, she probably would have wet herself. Call it cowardly if you want. Okay, it was cowardly. But...okay I don't really have an excuse. It was bad enough recounting the stockroom follies. ?What happens if Tom finds out you've been, uh...?? ?Unfaithful?? ?I was going to say something like sucking other dicks, but unfaithful might be better.? ?I'm surprised at your, um, directness.? ?Yeah. Sorry. These talks make me horny as hell.? ?Want me help you with that?? ?That would be unethical in all kinds of ways. No. I'm okay.? ?I ate a lot of pussy in my previous incarnation, with no complaints.? ?You're terrible.? ?No, I'm very good. Or you could just diddle yourself while we talk.? She shifted in her seat. ?Just let me see it. Give me a Sharon Stone peek.? ?Oh shit.? ?Last night, Tom came on my face. I took a selfie. Want to see it?? ?That would present a problem. If I looked at your selfie, I'm afraid I wouldn't be able to resist having sex with you.? ?Why would that be a problem?? ?Because then I would have to stop being your therapist. Ethics.? ?I don't want to stop therapy with you.? ?I don't want that either. I would be dishonest if I said I wasn't sorely tempted, but I'd rather continue with therapy than get into a sexual relationship with you.? ?I agree. And just for the record, you're very hot.? She was, in a milfy librarian kind of way. ?Thank you. And so are you, obviously.? ?Thank you. Want to talk about my date with Tom? Or the events with the hunk at work?? ?Let's stick with Tom. That seems more like a real relationship, while the other...? ?A dalliance.? ?Yes, good choice of words.? She shifted in her seat again. By now, I could tell when she was getting uncomfortable. ?Need to take a break?? ?No, I'm okay. How do you feel about that relationship?? ?I'm enjoying him. It. I'm enjoying the relationship.? ?But it isn't enough?? ?Apparently not. I mean, I can understand your confusion. I came in here week after week, meek and mild, and talked about maybe someday going out with a man, and now, suddenly, I seem to have become a trailer park slut. The kind of woman your mother warned you about. It confuses me, too.? ?How do you feel about that confusion?? ?Confused. What are you after, here?? ?Well, does the confusion worry you? Do you question your motives?? ?All the time. I'm trying to figure out what I want, and aside from being a promiscuous fellatrix, I don't have much of a clue.? She laughed. ?Fellatrix. I like that.? ?So do I. It's so much nicer than cocksucker.? ?More French. Everything sounds classier in French.? ?I know that I don't want to become a submissive, docile, domesticated woman. I'm finding that there's a lot of power inherent in being a feral woman, and that realization kind of surprised me.? ?I don't want to encourage behavior that might be mercenary, or cruel, but especially looking like you do, you can wield a lot of power over men.? She cleared her throat. ?Over women, too.? It was my turn to laugh. ?But I should use my power only for good, never for evil?? ?Something like that,? she said, grinning. ?It's that time again. I have to say that I enjoy these sessions more than I should, more than is professional, or decent.? I stood up. ?If you change your mind about, you know...? I winked. She said, ?I will. See you next week. Now, I have to go wring out my panties so I don't smell so much like cunt.? I replied, ?Oh, well played, Doctor.? ?Two can play at that game,? she said. And she laughed. ?I need someone to play second base,? Tom was saying. ?You in?? This wasn't as off the wall a question as you might think. Tom and I had first met on the baseball diamond in high school. I was an All- State shortstop for Broughton High School. Tom was an All-County pitcher for Sanderson High School. We were the stars of our teams, respectively. We became friends after the epic final series for the conference championship. After two games of the three game series, we were tied at one. The final game was played at Sanderson, before a sellout crowd. Tom was pitching for Sanderson. We were tied 2-2 after ten innings. In the bottom of the eleventh, I led off with a long single. The following batter sacrificed, advancing me to second. On the first pitch to the next batter, I stole third. A long fly out brought me home, and two strikeouts ended the inning. Tom came to the plate with one out, runners on second and third. He hit a screaming line drive at the gap to my right. I made a diving catch and jumped up to tag the runner coming from second. Double play. Game over. We both got baseball scholarships to UNC. I might have gone pro if I hadn't hurt my shoulder in my junior year. Tom pitched for four years, not terribly successfully, and wasn't drafted. As we learned earlier in the story, he went on to law school and became a lawyer. I became a bartender. Nine years later, I began my transition to become female. Now, sitting in a booth at McDonald's on his lunch hour, he seemed to be asking me to play again. ?But, Tom, I don't know anything about softball. I played baseball.? ?You don't have to know anything special to play softball on a City League Parks and Rec Co-Ed softball team. My second baseman got hurt, and I need a replacement. Will you help me out?? ?I don't know. I don't want to make a fool of myself, or you, either. I haven't swung a bat or thrown a ball for ten years. I haven't run anywhere in five years. I've given up the whole athlete thing. And it's fucking softball.? ?Look. After work, we can go up to Lions Park and run a few sprints, I'll pitch batting practice for you. I even have a glove for you. Then I'll buy you dinner anywhere you want.? ?Oh, all right. But it'll have to be Sullivan's Steakhouse. And if I can't hit a softball, the deal is off.? ?Thanks, Babe. You're the best. I'll pick you up after work.? He got up and gave me a perfunctory peck on the lips. ?Wait a minute, cowboy. You're going to have to kiss me like you mean it.? He kissed me like he meant it, until my tits tingled. And I walked home. Somewhere, in some closet at the house, I had a trunk that contained some mementos, and the only male clothes that I had not thrown away: my college baseball uniform and spikes. After some rummaging, I found the trunk and dragged it out. It was immediately obvious that the jersey was never going to fit. I tried to wiggle into my sliding shorts, but there was just no way. The pants were tight, but they would work for practice. I would need to go shopping at Dick's or somewhere before I played in a game, I thought. And what about a cup? How was I going to hide that? This was a dumb idea. And, you know, I was going to a whole lot of trouble for a guy who wasn't really my boyfriend, who hadn't reciprocated oral sex, who hadn't said he loved me, and who basically just stopped by to get a quick blowjob or two. So I was getting kind of cranky when he called me. It had only been forty five minutes since he had kissed me goodbye and made my tits tingle. I pushed the button and said, ?What?? more angrily than I really intended to. ?Hey, Sweetie, I was thinking about it, and I twisted your arm pretty hard. If you don't want to do this, that's okay. And I'm sorry if I took you for granted.? Well, that was more like it. ?I'll give it a try. But if it looks like I'll be an embarrassment, I'm out. Agreed?? ?Of course. I can't imagine you being anything less than a softball diva, but it's your decision, of course.? ?Okay. I need to buy sliding shorts and stuff. Maybe some less manly cleats.? ?I'll buy you anything you need for this. You're doing me a big favor, after all.? ?You just want to get head from me while I'm in baseball drag. Want me to wear a Broughton uniform?? ?Um, we'll have to discuss this in more detail this evening. My client is already very interested.? I assumed that someone had walked into his office. ?Your client. That's funny. Tell your client that we should be able to reach an accommodation. Right down my throat. With lots of suction. Until your client throws up in my mouth and I swallow.? Hitting a slow pitch softball is very different from hitting a baseball. The pitcher throws the pitch underhand in a high arc, and it crosses the plate going almost straight down, which is stupid. But those are the rules, and I agreed to try it. I missed the first five pitches horribly. I resolved to end the experiment if I missed another five. Then I hit the next three over the left field fence. Well, okay then. ?Damn, Jill, you're a natural!? ?That's what you said about...some other skills.? I hit all the next dozen or so pitches, only one over the fence. I told Tom I'd need another session of batting practice, and some practice fielding that stupid big ball. He said they'd have batting practice and fielding practice before the game. Not at all the same, coach. But okay, said the softball diva. I suspected that we would both regret this whole thing. We went back to my place so I could shower before dinner. (Because I don't want to go out to a nice dinner smelling like infield dirt and sweat, that's why.) I excused myself and went into the bathroom. I thought it was possible that tonight might be the night I'd let Tom fuck me, so my plan was to give myself an enema while taking a shower. I mixed it up and filled my ass up with the solution, then I stepped into the shower. After a few minutes, about the time I felt the urge to expel the enema solution, Tom stepped in, too. He had never seen me completely naked, with my nonstandard plumbing obviously present, so I was a little nervous about that. I mean, he knew, of course, that I had one, but it hadn't been right there, exhibit A, as it were. And shaved and all. I couldn't even hide behind pubic hair. My other problem, and the one that worried me more than my little wee- wee on display, was the enema. I didn't want to have to explain that if it happened that he wanted to shove his dick up my ass, and if it happened that I wanted him to, I didn't want to get shit all over his dick. I didn't want to explain that I was I was doing an internal fuck prep just in case. It would seem like I was taking things for granted. And time was running out on my ability to hold it, and it would be fairly noisy and disgusting when I let it go. ?Hi, Tom. I'm afraid I'm going to have to step out for just a minute.? ?I'm sorry. I shouldn't have just gotten in with no warning.? ?That's not it. I have to use the toilet. Promise not to listen.? ?What?? ?It's going to be unladylike for just a minute or two. I apologize in advance. Stay right here. I'll be right back, better than ever.? It was unladylike, but not as bad as it might have been. I wiped and squirted some KY up there, just in case. I stepped back in, blushing prettily, I'm sure. ?Um, if you're not feeling well, we don't have to do dinner tonight,? he said, all solicitous and concerned, the sweet man. ?I feel fine. The problem is that I was a Boy Scout, and I've never gotten over it.? He put his arms around me. ?Trustworthy, loyal...? ?It's the Be Prepared part.? ?Oh?? He raised an eyebrow. ?It's like this: I was thinking there might be a chance you'd want to fuck me tonight, so I took an enema to get myself cleaned out for you. Just in case. If you don't want to, that's okay,? I added hastily. How humiliating could this possibly be? ?Telling you I was preparing for it kind of takes all the romance and spontaneity out of it. I'm sorry for that.? Then he kissed me. Oh, God, did he kiss me. And he had all those big, wet, slippery muscles wrapped around my top half, and that big hard cock pressing on my little soft cock. Oh, my goodness. It was glorious. ?Do you want to make love?? he asked me. ?More than anything,? I replied. ?But this is another one of those things I've never done before, so I'm not sure how it will go.? I added, spoiling the whole mood. ?Don't worry. I'll be gentle.? ?Not too gentle.? ?No, not too gentle.? I got out and grabbed my towel and one for Tom out of the vanity. We dried off some, and he picked me up and carried me to the bed. Carried me, I tell you, like a bride across the threshold, except damp and naked. He put me down with my ass up and face down. That's sexy and all, but I wanted to do it the first time face to face. I told him so. I rolled over and pulled my knees up to my ears. ?Lube?? he asked. I gestured to the bedside table. ?In the drawer.? He opened the drawer and found the lube and the vibrator and dildo. ?Toys,? he said. ?Boy Scout,? I replied. He made the appropriate preparations, kissed me deeply, and pushed it, slowly and gently, all the way in. When he was balls deep, he asked me how it felt. ?So...? I meant to say So Good, but by then he was pulling it out. He started moving back in, and I said ?So? again, but now, it was hitting my prostate squarely. It was like nothing I'd ever felt. I just moaned. He started upping the tempo slowly, and with every stroke he was hitting my prostate. I felt something like an orgasm, but different, begin to build. It was centered in my ass, but it was spreading through my whole body. It was an orgasm, but it never peaked and ended, it just washed over me in waves. My body tensed and shook and my back arched, and I moaned and shrieked and called out for God and for Tom, and it kept on going, getting more and more intense. At some point, my penis leaked semen, not squirting, but undeniably an ejaculation. Tom kept banging away at my prostate until finally, he came and collapsed on top of me. I covered his face with kisses. ?How was it?? I asked him. ?I guess I don't have to ask how it was for you.? ?Why's that?? ?You expressed yourself forcefully on the subject.? ?Was I too loud?? ?Sweetie, there is no such thing as too loud in that context. But your neighbors might disagree.? ?You were the one slamming the bed against the wall.? That, I thought, while lying on the bed panting, changes everything. In the first place, I didn't have to be in a big hurry to have a vagina installed, because being fucked in a synthetic vagina couldn't possibly be better than what I had just experienced. Secondly, this expanded my horizons for potential, theoretical, hypothetical sluttiness. Purely hypothetically, I could be slutty with two men simultaneously, if the opportunity presented itself, and I felt like it. If I felt like it. As if I wouldn't feel like it. Ha! Thirdly, the whole nature of my sex life swung from being something that existed to please others, to something that?at least sometimes?existed to satisfy me. And just for a fleeting moment, I thought about Seabiscuit. According to the league rules, teams had to have at least four female starting players. Tom assured me that no one would question my sex, although I would absolutely have gone through all the hormones, the surgery, and all the rest of the humiliation and expense in order to get away with being a ringer for Parks and Rec Co-Ed Softball Team. Totally. I'm kidding, of course, but you have to remember that this is North Carolina, where the legislature passed a bathroom bill, overrode the governor's veto and appealed it all the way to the United States Supreme Court, in order to keep people like me from using the women's bathroom. But I digress. I was the fourth female on the team. I gave him the quota he needed. Tom hadn't explained that part of the situation. I couldn't quit without forcing a forfeit. Tom guessed correctly that I was competitive enough to make that outcome unlikely. Nothing was stopping me from being bitchy, however. The other three females were Heather, a short, busty nineteen-year-old, Mandy, a tall mid-thirties mommy, and Kaiti, a Barbie Doll. Heather played shortstop, and was dressed in yoga pants and spikes. Judging by the pregame practice, she could field, throw to first on one hop, and hit a little. Mandy played right field, wore sweats and had a formidable arm. Kaiti was ornamental. She wore booty shorts and pink sneakers, and she was positioned in short center. When a ball was hit toward her, she said ?Eek,? and jumped out of the way. But she was undeniably ornamental. I figured she was fucking somebody, or she wouldn't be playing. I wondered whether she was a switch hitter, so to speak. The guys on the team were all reasonably competent former athletes in their thirties. Off the field, they looked like a law firm. I recognized a couple of them as regulars at the bar where I worked. Mandy and four of the guys, including Tom, had been playing together on this team for five or six years. There were Tom, Bill the first basemen, Ron the left fielder, Ashraf the center fielder, and Willie on third. The catcher was a big black guy named TJ. There wasn't a lefty in the bunch, although back in the day, I could bat from either side. The name of our team was the Scorpions. We were 7-4 for the season, in second place in the league. The team we were playing that night were the Cardinals, 8-3, first in the league. If we won, we'd be tied for first. Not that I actually gave a fuck. The players on my team talked a lot about the standings, and a couple of the guys, besides Tom, were interested in getting to know me better. The girls didn't seem to be able to see me. They certainly didn't have anything welcoming to say. One of the guys gave me a pep talk: ?If you don't get a hit, that's okay. It's not a big deal.? He patted my hand. Yeah, sure, dude. And I was sure he'd be willing to comfort me by giving me something to suck on. I came to bat in the top of the first with two out and a runner on second. I put the first pitch over the left field fence. That's how it's done, bitches. I enjoyed my trot around the bases. I liked rubbing their noses in it. I liked the way my ass jiggled as I ran. I liked the dirty looks the other team gave me, all except their third base woman, a cute, young brunette who didn't look like a dyke, but who gave me an absolutely radiant smile which I returned with a wink. I would have to try to hit a triple, I thought. Ron flied out to center to end the inning. Tom pitched three innings of no-hit ball, and we didn't score again, although we threatened in the third and again in the fourth, when I doubled, stole third and was left stranded. I did get a little time with my new friend, Leslie, the third base woman. She wrote her phone number on my arm in sharpie. Subtle? No. Effective? You bet. The fifth was uneventful, and in the sixth, the final inning by league rules, we went down in order. The Cardinals' leadoff batter singled. The next batter struck out. The third batter hit a long single which advanced the runner to third. With one out and runners on the corners, I told Heather to be ready for the double play, and I'm glad I did. The batter hit one right past Tom, a hard grounder right up the middle. I dove for it, scooped it up, flipped it to Mandy from flat on my back. She stepped on the bag and fired it off to first, beating the runner by a half step to win the game. I jumped up, gave Heather a high five, and got lifted off the ground by Tom. Yeah, that's how it's done, bitches, that's how it's done. The next day, I called Leslie. ?I know who you are. Who you were,? she informed me. ?You make it sound like I'm dead.? ?You used to be Jim Trent,? she said. ?Who did you used to be?? I responded. I have nothing to hide, at least as far as my gender is concerned. But it was making me a little nervous that she knew about me after just meeting me once. ?When you were playing for Broughton, and dating Katherine Dixon...? ?Kathy, yeah I remember her...? ?She used to bring her little sister to the games.? ?Sure,? I said. A picture of a shy kid keeping score on the bench beside our dugout came to mind. ?I used to be the little sister. I mean I'm still her sister, but I'm not as little. I had a horrible crush on you.? ?Really?? ?Oh, I was totally in love. And that was about the time I discovered masturbation. I must have had a couple of thousand orgasms fantasizing about you.? ?Wow. Thanks, I guess. And I'm sorry I didn't have any idea.? ?Or what? You'd have helped me out?? ?No, I...? ?I'm pulling your chain. Want to get a drink sometime?? This chick got right to the point. ?Sure, I guess. When did you have in mind?? ?How about now?? This was moving pretty fast. I felt kind of off balance, but I was curious and a little freaked out. ?Okay, I guess so. Do you have a place in mind?? ?I'm sitting in The Office.? ?Let me get dressed...? ?You're naked?? ?No, I'm just not dressed appropriately.? ?For this dump?? I didn't know why I was having a drink with this chick, or why she was busting what was left of my balls like this. And, to be honest, I really didn't know what ?appropriately dressed? meant in the context of an impromptu quasi-date with an ex-girlfriend's little sister in a sleazy dive bar at 1:00 in the afternoon. Does one wear a skirt to that? Heels? A leather teddy? Two Band-Aids and a jock strap? In the end, I wore jeans, a Grateful Dead tee shirt and sneakers. But I wore a cute bra, just in case. This chick was making me nuts. ?There she is,? she announced. Well, I was, of course. ?Want to play pool?? I asked, hopefully. ?No. My sister says you are the best pussy eater ever.? She smiled. ?Is there any truth to that?? ?I don't know. I mean, I haven't had any complaints.? I felt disoriented. ?My sister said you loved eating her pussy.? ?Well...? ?She said you called it delicious.? ?It was...? ?She's a skank.? ?She's your sister.? I was kind of shocked. ?Yeah, whatever. I ate her pussy, and it was nothing special. Mine's much nicer.? ?No doubt. Wait, you ate your sister's pussy?? ?Yeah, when you stopped eating it, somebody had to step in. It wasn't going to eat itself.? ?So you stepped in.? ?Yeah, three, four times a day. It got old.? ?And she didn't reciprocate?? ?Of course she reciprocated.? She gave me a look. ?If she didn't, that would be weird, right? What made you think she didn't reciprocate?? ?I don't know...? ?You're not still hung up on her, are you?? ?No, of course not.? I was getting a headache. ?You are much hotter as a girl,? she announced. ?I think so, too.? ?The breasts rock.? ?That's the general consensus.? I needed a beer. I went to get a pitcher, shaking my head. When I returned to the table, she told me my ass was awesome. And it is. ?Are they implants, or is that all you?? ?Some of both. I got the implants early on, and my ass kept growing more than I expected.? ?Is it still growing?? ?Not much anymore.? ?I'll bet your boyfriend loves it.? ?Yeah, he's a fan.? I smiled, thinking about the events of a couple nights ago. ?So am I. Would you sit on my face sometime?? ?Do you know anything about filters, or boundries, or...or...? ?Manners? Not much. I just figured that since you're going to eat my pussy, I should reciprocate.? ?By having me sit on your face.? ?So I can eat your ass.? ?I know why faces get sat on. I've had a little sexual experience. What makes you think I'm going to eat your pussy?? ?It's going to be right above your mouth while I suck your dick. You won't be able to resist.? ?You're pretty sure of that?? ?It's fate. You'll see.? ?Fate?? ?Yup. Wait and see.? I tried to change the subject with talk about the softball game. No luck. The weather. No luck. I considered asking her about her sister, but I thought better of it. I didn't want to just get up and leave, because that would be rude, right? Anyway, I called her, so she had my number. She could call me at embarrassing times. She knew my secret, and at least theoretically, she could blackmail me and get me disqualified from playing City League Parks and Rec Co-ed Softball. Before the game, I would have jumped at the chance to be disqualified, but now, I kind of liked being a softball diva. It was all very confusing. ?Where do you live,? she asked. ?Couple of blocks up Boylan.? ?Let's go.? ?Where?? ?To your house.? ?Why?? ?So that we can have sex. You're going to eat my pussy, and I'm going to suck your dick, and you're going to sit on my face, then we're going to fuck. Does any of this sound familiar to you? Jesus, Kathy said you were a little slow.? ?Even if I agreed to all this, I'm not sure that fucking is in the cards.? ?Yeah, I figured. I have this.? She pulled a big strap-on dildo out of her bag and held it up. ?Put that away. I may be a little slow, but at least I don't go waving sex toys around in The Office. If you're not careful, we could be the first women ever thrown out of this dump.? ?So you'd prefer a more private venue?? ?Well, yeah, I guess. But I'm not sure how I feel about fucking you with a strap-on.? ?Oh, no. This cock is mine. I'm going to be doing the fucking, sweet cheeks.? So I guess it was fate, or she was just so insistent that I couldn't say no, or something. We walked up the street to my place, me bouncing and jiggling, she talking incessantly about whether she was lesbian, or bi, or polyamorous, or queer, or trans. She was sure she was something, and she seemed to have tried it all. Whatever else you could say about Leslie, she was not shy. ?One of the guys on the Scorpions is your boyfriend, right?? ?Yup.? ?The pitcher.? ?Yup.? ?He's pretty hot. Think he'd go for a threesome?? ?No, I don't.? ?Because he's too conservative?? I quickly thought that I didn't know how anyone could be open minded enough to date a trans woman, but too conservative to add a third to the mix. It seemed improbable. So I said, ?No, because I'd bite his dick off if he proposed it.? That slowed her down a little. And, frankly, it surprised me. ?I'm sorry. That was out of line. You should give me a spanking.? So I did. I spanked her hard until her ass glowed red, and sat on her face. Then I ate her to two orgasms. Her pussy actually was delicious, and nicer than Kathy's. And she sucked my little cock. Then I gave her dildo a sloppy, theatrical deep throat blowjob before she fucked my ass until I came. All in all, a pretty nice afternoon. Then I kissed her goodbye, stuck a butt plug up my ass, and went to work. Why the butt plug, you ask? Because my ass felt empty, not that it's any of your business, and I thought it would add interest to the evening. She had been impressed with the dildo blowjob and with the fact that I could orgasm from ass fucking. And she had waxed lyrical, more or less, about my cunnilingus skills. I was pretty sure, as I walked into the restaurant and punched in, that she was already on the phone with Kathy, telling her all about it. And gloating. I know I'm not dishing on all the details of the sex with Leslie, all the licking and moaning and gasping and grunting and all the sights, smells, tastes and sounds of that hour. I'm sorry I'm not feeding your voyeuristic fantasies, but while it was fun, orgasmic and all, I wasn't feeling it. Maybe it was that I'm not as bisexual as I assumed I was. All those women I slept with in my previous incarnation were worth the chase and the conquest, right? I genuinely cared about them, didn't I? My response, sexual and emotional, to women, and the pain of losing them, were real, weren't they? In that moment, I wasn't sure. I also contemplated the possibility that it wasn't the sex of my partner, but the identity of my partner that mattered to me. What, then, of my dalliances? What of Stockroom Follies and Seabiscuit? Where do these fit into the picture? Do I find satisfaction in these encounters because they are men? Or because I used them for my purposes, used them for validation of my power as a woman? These experiences undoubtedly validated my attractiveness, my sexiness, my skill as a fellatrix, my ability to tell men what to do and have them do it. (I don't know how much power it takes to tell a man to cum in my mouth and have him do it. More to tell him not to, I think.) As I was thinking about these questions, old, fat, gross Seabiscuit Harry appeared behind the bar, smiling lewdly and smelling strongly of Old Spice. ?Hi, Holly,? he said. ?Before you start, the answer is no, Harry. I have too much on my mind to play games with you tonight.? He reached out and grabbed a handful of my ass. ?Take your hand off of that before I knock your dentures down your throat,? I growled. He did. ?Just trying to be friendly to my favorite employee...? ?Don't. I'm in no mood.? He backed away muttering excuses. He may have the biggest dick in three counties, but he's still a fucking pig. I considered the possibility that I might be giving up any chance I might have of seeing that horse cock again, but then I realized that no matter what I said or did to him, that cock would always be available to me. All I had to do was tell him to whip it out, and he would. Guaranteed. That realization stopped me in my tracks. I could treat him like shit for the rest of time, and he would always be back for more. So would Stockroom Follies. And I suspected so would Leslie. But what about Tom? This was a whole different thing, and I was unclear why. Without any decision or even conscious thought, I had drifted into being something approximating his girlfriend. I wasn't sure what rights, privileges and obligations came with that title, if any. Tom was an old friend. We had known each other for a dozen years. I didn't want to screw up our friendship, and I didn't want to screw up our?what was it? A romance?--either. A romance. I paused in the act of polishing a beer glass. A romance? What the fuck? How did this even happen? I wanted to be female. I've wanted it since I was so high. But I wanted to be a full grown woman, not a teenage girl who falls in love with the first man to show an interest in her. Not really the first man to show an interest--There were plenty of guys who looked down my shirt or made off color suggestions?But the first...Oh, hell. The first to kiss me. The first to stick his dick in me. The first to make my tits tingle. The first to make me want to wrap my arms around him and have him wrap his arms around me. Oh. My. God. A customer broke through my reverie by ordering a Manhattan. Fucking Manhattan drinkers. Ruining a perfectly good glass of bourbon. And then put a fucking cherry in it. What is this? Shirley Temple time? I served the idiot his drink with something resembling a smile and went back to polishing glasses. And then I started to cry. I don't cry. I didn't cry when my father died. I didn't cry when my dog got run over. I never cry. But I was crying now. I sat down on the greasy anti-fatigue mat behind the bar, sobbing, just sobbing. Stockroom Follies came running and tried to comfort me, but I wasn't having it. Unable to stem the tide of tears, he hoisted me to my feet and dragged me to Seabiscuit's office. He dropped me onto the couch and stepped back. One of my boobs had slipped free of my bra and top, but I didn't care. Stockroom Follies looked like he wanted to help me get it back where it belonged, but he didn't dare touch it. Eventually, I stuffed it back into its containment vessel. He stood there looking down at me alongside Seabiscuit, neither having the faintest clue what to do or say. And I kept crying. I remember beginning a soliloquy that was supposed to explain my emotional breakdown, but it came out like this: ?Dammit...dammit...dammit....muscles, and the enema and all ..dammit... motherfucker, fuck, fuck, fuck...and all over my face... motherfucker... dammit...and in my ass, too...dammit...dammit...motherfucker...? I gave up and just cried for a few more minutes, while Seabiscuit and Stockroom Follies looked on. Seabiscuit asked Stockroom Follies if I was drunk. ?No!? I wailed, ?I'm in motherfucking love, dammit!? I went on in this vein for some time before I finally wound down. ?Do you want a drink?? Seabiscuit asked solicitously. Evidently, in his mind, if alcohol wasn't the problem, it must be the solution. ?Anything but a Manhattan,? I wailed. Stockroom Follies brought me tequila. I drank some, right out of the bottle, and then some more. I curled up in a ball at the end of the couch clutching the bottle to my chest with my eyes closed, hiccupping and sniffling. ?I hate tequila,? I finally told them, but I didn't let go of the bottle. Eventually, I got myself to the bathroom and washed the black streaks off my face. I looked a wreck, even so. My eyes were red, my hair was everywhere, and half the water I had used to wash my face had run down into my bra. My shirt was soaked. My pants were dirty in the back from sitting on the floor. ?I'm going home,? I announced. ?Who's going to tend bar?? Seabiscuit asked. I eyed him coldly, and said quietly and calmly, ?Not one single fuck do I give.? That confused him. ?What did she say?? But by then I was out the door. I pulled out my phone and called Tom. This was all his fault. ?What are you doing?? I demanded. ?Thinking about you and jerking off,? he replied. ?Well, put that thing away and come get me. I'm in front of the restaurant.? In a surprisingly short time, he was there in his Porsche, looking absolutely adorable. ?What happened to you?? ?Open the fucking door and I'll tell you.? He did. I got in. ?Drive,? I said. ?What happened?? he demanded. ?Drive,? I said again. He did. ?I fell in love,? I said. He swerved and almost hit a car coming out of the old Pine State Creamery parking lot. ?Watch out!? I screamed. He stopped in the middle of the street. ?With you. I didn't mean to, but I did. And it's your fault.? He just stared at me. ?So I assume you've been crying...? ?Yes, Tom, I've been crying.? I came very close to adding ?you stupid motherfucker,? but I didn't. ?But why?? ?Because you made me fall in love with you. Against my will.? That may seem to have been a stupid thing to say, but that's what I said. And I meant it, and I blamed Tom. He was too handsome, and too nice, and too good a kisser, and too strong, with those big biceps, and he carried me to the bed when we made love, and he made me wake the neighbors. ?But Jill, that's a good thing.? ?How do you figure?? ?Because I'm in love with you, too.? ?You're just saying that because it's your fault.? ?Well, it's your fault I fell in love with you. So we're even.? ?Really?? ?Yes, Jill, really.? ?Then we should go to my place and fuck.? ?Yes.? ?But I have a butt plug up my ass,? I announced, suddenly remembering it was there. ?Then you can fuck me for a change. Would you like that?? ?Seems kind of kinky and wrong.? ?So you don't want to?? ?The hell I don't. I'll make you call me your daddy.? I grabbed his big bicep and laughed. ?Probably not. Want to suck on it, too?? ?Absolutely. That's what I was fantasizing about when you interrupted me.? ?Really?? ?Yes, Jill, really.?