Entry#1
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               WARNING:

               These journal entries are a work of complete fiction.
               Attempting to recreate any situations or actions described in
               this fiction may be extremely harmful or dangerous.
               

February 2nd, 2016 . Am I a "Tranny Chaser"? That term has always seemed so negative to me. I don't know very much about Transsexuals, transgenders, cross-dressers, etc. All I know is I had sex with one and it was the greatest sex I've ever had in my life. Even though it may have cost me my best friend, I can't say that I regret it, but now I'm so confused. Everybody wants a meaningful intimate connection to another person and a relationship based on compatibility, love and respect, but what about sex? Sex is always a part of a romantic relationship. If my sexual preference is for a pre-opp female transgender, how do I even begin to approach a relationship? Is there any chance of a happy relationship with someone in the middle of a state of transformation? What happens when they finish the transformation and are no longer the gender of my sexual preference? I'm freaking out over a playful text that a friend sent me. Is she my friend, or is it more? If it's more, will I lose her forever if the relationship fails? How can I start a relationship with her now, when I don't even what my own sexuality is? . This all started when I was on my knees. The mix of fear and excitement was intoxicating. Maxine stood over me. I slid my hands up her thighs and under her skirt. She smiled down at me, her long blonde hair draping around both side of her neck and fanning across the pointy nipples of her ample breasts. The cloth of her short, tight skirt was to stretched towards my face as I slowly hiked it up to her waist. Her penis was fully erect and throbbing, ready to tear its way out of her translucent panties and as the cloth pushed it up and to the left. I licked the cloth over her shaft and watched her penis react with a quick flex, then return to it's slow throbbing. I grabbed the thin elastic band of her underwear and slowly let her penis free from it's hold. The thin white veil slid down and over the fleshy head of her pulsating cock and I found myself breathing heavily as I stared at it. I had never been this close to a penis before. I realized I had no idea what to do next. I had fantasized about this moment for years, and finally, it was here. But that's not where I should start. The first thing I should have written is that I'm a heterosexual man(at least I always fooled myself into believing I was), somewhere near the age of thirty. Until that night I went out with my friend Sarah, had never realized how much of a coward I had been in life. . I remember driving her car. The wind in my hair felt amazing as we came to speed on the highway. The setting sun was warm and the top of Sarah's convertible clicked away into it's folds. The GPS navigation instructed me to stay on the highway for twenty-seven miles. I had no idea where we were going. She imputed the location before I got into the car and would not give a single hint as to where. Why I was driving her car seems relevant to the fact that I would later be staring at a beautiful pre-opp transsexual's penis, less than an inch from my face, too frozen with fear to do what every instinct in my body was telling me to do. Sarah was four years younger than me, but we had been friends for more than a decade. We had a few physical flings when I was in between relationships, but she made it clear that she was in no way interested in the distractions of a relationship until after she had won at least one Olympic medal for speed skating. She was good at it, and she was focused. I've seen her kick more than one man to the curb over the years for getting too attached. But she had yet to make it through final cuts for the team. She had said she wanted to blow off steam tonight and go maybe more than a little nuts. When I showed up at her house, she told me to leave my car and drive hers. She claims it's so she doesn't drink and drive, but it usually ends up with her inviting me to stay the night. She was tall and lean with an athletic build and fire red hair. It had been a while since we hung out, and she seemed pretty wound up about something. I loved the ways she used me to relieve her tension. I had a feeling I was getting lucky tonight. I sneakily checked her out as she stretched her arms high and pushed out her chest. SARAH I see you looking over here. I shrugged and made no attempt to hide my gaze as I shifted it between her and the traffic. She smiled wickedly and stretched more. SARAH (CONT'D) Don't think that just because you're driving, you're getting lucky tonight. I need a hard pounding from someone over the foot length tonight. She playfully undid two of her blouse buttons and spread her shirt to show her cleavage. Her breasts were small but perky. She loved wearing super tight button up tops with no bra. I told her happy hunting and that I'd do what I could to help. I also told her that if she found a guy that actually had over a foot of penis to call me so I could see it for myself. She laughed. It had actually happened once or twice over the years. Us going home separately, not the foot long penis. We both agreed that should either one of us get an opportunity we didn't want to miss, that the other would take a taxi home and no hard feelings. She was, of course ahead of me as far as numbers went. But surprisingly she had actually helped me seal the deal with another woman on more than one occasion. Our relationship was beautiful. It wasn't until I had a penis so close to my lips that I could kiss it, that for the first time since I've known her, I feared what would happen if my relationship with Sarah changed. . It was definitely a gay bar. The population of women was at most one tenth that of men. I had been in clubs where the female population dwindled before, but the men in those clubs were no where near as happy as they were here. We waited at the bar for our drinks. Opposite the front doors, the bar gave way to a large dance floor. Most of the few women in the place were coupled on the dance floor. I watched the room and just as I was starting to feel uneasy I noticed a few things that instantly made me love this place. There were no thugs, or wanna-be gangsters strutting around trying to look hard. There were no underaged kids waiting for their moment to burst into obnoxious teen hijinks. The music thumped from the dance floor, but no one had to scream over it to have a conversation. Within minutes of arriving, I was honestly saddened that I hadn't found places like these earlier in my life. I turned back to Sarah and arched my eye brow to "are you insane" level. SARAH (CONT'D) What? I asked her if she knew this was a gay bar before we got here and she nodded yes. She had the twinkle in her eye, and I knew she was planning to get us into some sort of mischief. I asked her why she would come to a place like this in search of a foot long thrusting. Even if she found her Moby Dick, it's more like I'd be the one to go home with it. She gave a very sinister grin when I said that. SARAH (CONT'D) Just promise me you'll let me watch. I grimaced, but the idea was turning me on. I tried not to let it show. She cocked her head and looked me in the eyes. SARAH (CONT'D) I knew it. I never could lie to her, but I lied to my for years. Ever since the first time I saw a porn movie, I was always just as interested in seeing the men naked as the women. My collection of porn magazines was always sprinkled with one of two issues of playgirl. Truth be told it was my deepest darkest secret. I never told anyone; especially not her, but some how she had managed to piece it together. At this point in the evening, I began to realize the potential of the situation. I was scared and instinctively changed the subject. I asked her how the tryouts for the Olympics went. Angst swept across her face, and she forced her smiled back. SARAH (CONT'D) I made alternate. I congratulated her and proclaimed how awesome that is, but she sighed, speaking volumes of "not enough to be satisfied". She opened her mouth, but before she could speak the bar tender popped up with our drinks. BARTENDER Two Midori Sours, on the house. The bartender was a tall large men in his forties. He was handsome, but a little gruff looking with his chin full of stubble. He winked at me. I had no idea how to respond to that, so I just smiled politely. SARAH Thanks. We're on a quest to find a foot long penis. She looked him up and down. SARAH (CONT'D) You wouldn't happen to be hiding that many inches behind the bar would you, big guy? I was in disbelief. Sarah was brazen, but she had never been this aggressive before. The bartender smiled at me as if he were going to whisk my away to the tropics for the weekend. BARTENDER Not quite that big, but if size is your thing, I'm sure I could spread you to satisfaction. At this point I have tell you that I was completely unaware of my facial expression. My mind was doing flips. I had never in my life been given the direct offer of having my ass spread by another man's penis. Not only was I completely unprepared to understand my emotional response to the situation, but I couldn't for the life of me figure out why I was so turned on by it. A full erection was running down the left leg of my pants. Sarah knew I was floundering and was having no end of joy watching. It seemed like an eternity, the second and a half, before she swooped in and saved me from drowning. SARAH He's so shy! Look at him blush! Apparently I was blushing. BARTENDER Don't worry, I'll put the word out on your quest. You two have a great time. He winked again, then walked down the bar to serve some other customers. SARAH I'm going to have so much fun with you tonight. Come on, let's go upstairs. I asked her to give me a minute and looked down at the penis shaped bulge in my pants. She laughed hard and crabbed me by the penis pulling me to my feet. SARAH (CONT'D) Hey bartender! Look what you did to my friend over here. The bartender as well as half the bar looked over as Sarah squeezed my penis hard, then released it. I was pitching a full tent. Trying to walk through the crowd with her, at least fifteen people looking square at my erection. A few whistles and smiles were all that came before everyone turned their attention back to their own affairs. Sarah grabbed me by the penis again and led me across the dance floor. I was relieved to see I wasn't the only person with hands on their private parts. A lesbian couple smiled at us as we passed; a short haired woman danced while her partner cupped her breasts from behind. Their hips swayed in sync as the woman in front had her breasts caressed and fondled. The dance floor was bigger than it looked from the bar. At one end, stairs led up the second level. Sarah let go of my croth as we climbed them. I was holding both of our drinks as I followed her up. Her ass looked so round and toned in those bright pink hot-pants she wore. I wanted to squeeze it so bad when our place on the stairs put it at my eye level. The second floor opened into a horse shoe that overlooked the dance floor. We saw a busser cleaning a table and swooped down on it. . We spent the next hour taking shots and watching the bodies below us move, while Sarah evaded questions about the Olympic try outs. She was tipsy to the point of hiccupping before she admitting to bringing me here just to mess with me. That she was getting stress relief and sadistic pleasure out of forcing me to deal with all the homosexual hints she picked up on over the years. By now, she had hit on our gay waiter several times, and asked just about every man who walked by how long their penis was. I assured her that I was having a great time. I was a little tipsy myself and a silence grew between us. It wasn't awkward. We had moved past awkward silences years ago. It was comfortable and warm. We smiled at each other and I swear would have kissed if a man named James hadn't sat down and started talking. JAMES Hi. I don't want to speak out of place... James was clearly a tiny bit more drunk than we were. JAMES (CONT'D) But I heard there's a strait girl looking for a well endowed man up here. Sarah looked at me as if asking permission. I smiled and asked James how many inches he had. He answered confidently. JAMES (CONT'D) A little over eight. SARAH Sorry James. I've got nine and a half waiting on stand by. She gestured towards me and I shrugged apologetically. JAMES Can't blame a guy for trying. But if your seriously looking for over a foot, I think I can help. Sarah's eyes opened wide and her smile spread ear to ear. SARAH Really? JAMES Yeah, but the problem is my friend really has on crush on your boyfriend, here. Sarah looked at me with huge puppy dog eyes. James looked at me with a raised brow. SARAH Please? She drew out the please and pouted her lips. I couldn't resist. I told James to tell his friend we were down for a threesome, but to make sure his friend understands that I'm a virgin. James giggled to himself and pulled out a phone as he waved and walked away. I swear there was more to the conversation with James, but for the sake of this journal, I omitted a few really funny jokes and one or two bad puns. I told Sarah how unsure of myself I was and she took my hand. SARAH (CONT'D) Trust me. I'll be right there to help you every step of the way. The waiter came back and brought Sarah another drink. I was drinking soda for the rest of the night or we'd be taking a taxi home together. Waiting for James friend to arrive seemed to take forever. Looking back I realize that it was all of twenty minutes. . Maxine sat down at the table. Sarah and I both stared at her with confusion. She was a busty, curvy blonde with a very pretty face wearing a skirt and loose sweater that draped off of one shoulder. MAXINE Don't just stare, I thought we were going to get to know each other. We looked at each other, then at her. MAXINE (CONT'D) My friend James said you wanted to meet me, and maybe the three of us could have a good time. SARAH I'm sorry. I think he mixed things up a little. I- I interjected a we to show my support. Sarah smiled and corrected herself. SARAH (CONT'D) We were looking for a man with twelve or more inches. Maxine smiled and stood up, rubbing the front her skirt. She reached her hand underneath it and shifted her hips. A long soft penis flopped out between her thighs. She fixed the position of her skirt so that we could see just how far her thick flaccid penis dangling. MAXINE Sixteen when it's hard. She reached up her skirt and carefully tucked her penis away before sitting down. I searched for words, but they were gone. Sarah just smiled and took one of Maxine's hands. SARAH I'm sorry I ever doubted you. It was another five minutes before I regained the ability to speak. After that, it was the fastest hour of my life ending with Sarah speaking these words. SARAH (CONT'D) Let's get the fuck out of here and do this, already! . The hotel room was nothing special. The three of us were on the bed, on our knees, facing each other. We took turns kissing, letting our hands explore each others bodies. I slid my hand under Maxine's sweater, and found she wasn't wearing a bra. Her breasts were soft and heavy and I felt Sarah's hand moving across her chest over mine. She moaned as we gently pinched her nipples in unison. We wrapped our arms around each other in a three way embrace that turned into petting and then squeezing each other ass cheeks hard. The make out session went on for almost an hour before Sarah rocked back slightly and ripped open her blouse. Maxine and I lifted each other's shirts over our heads and tossed them playfully in opposite directions. We both looked at Sarah's chest a moment, then leaned in as she put her hands on the back of our heads. Sarah's areolas were large and puffy. I filled my mouth with one of them and sucked hard, watching Maxine do the same to her other nipple. Sarah panted out "oh's" and "yeses". We switched and Sarah and I leaned in to Maxine's chest. Her breasts were large with smaller areolas sitting low on the curve. Her nipples were pointy and erect, inverting slightly at the tip. I licked and teased one, while Sarah sucked hard on the other. Then we switched again and the two women pleasured my nipples. The feeling was indescribable. My cock raged against my pants and I was sure I was going to cream my jeans before I even unbuttoned them. They stopped and couldn't help touching myself. I put a hand on my penis and rubbed gently, trying to keep it from exploding in my pants. Maxine was doing the same. The tiny skirt she wore looked like it was going to rip apart at the seams. Her cock was enormous and stretched it around her hips like a rubber band. SARAH (CONT'D) This is wrong! Maxine and I had no idea what was going on. Sarah slowly stepped off of the bed and folded her arms staring at me accusingly. SARAH (CONT'D) We've been making out for almost an hour and you, sir, have yet to show Maxine's cock any love. Maxine was still rubbing her cock and nodded in agreement as she looked at me, then back at Sarah. MAXINE That's so true. How do you want to play this? Sarah unfolded her arms and looked me in the eyes with a devious smile. I knew I was in for trouble. SARAH This is how it's going to go. I'm going to walk you through your first blow job, and after Maxine blows her hot sticky cum all over your face, your going to suck her cock until it's hard again. Then she's going to put that huge monster of hers deep into my tight pussy. You're going to shove that thick rod of yours as far up her ass as it will go, and you're both going to pound your hips until you've smashed my little pussy to pieces. Any questions? She stood with her hands on her hips waiting for a response. Maxine and I both gave an eager "yes ma'am!", then Sarah led our new friend to the foot of the bed. She waited there while Sarah led me down to my knees in front of her. I slid my hands under her skirt and hiked it up to her waist; then slowly pulled her panties down over the head of her enormous cock. There I was, on my knees with sixteen inches of hard veiny flesh at my lips. Just the head of her penis looked like more than I could fit in my mouth, yet everything inside me wanted to swallow it whole. Her penis looked ready to explode. I knew the moment I open my lips to let it slide into my mouth a blast of cum would fill it. I was frozen. Then I heard Sarah's soft voice in my left ear. SARAH (CONT'D) I know all of your instincts are telling you to try and swallow this monster, but when a penis is already this hard, that's the worst thing you can do. I started thinking about the last time Sarah gave me a blow job, and how great she was at it. Maxine's urethra opened and let out drops of thick syrupy pre-cum. It oozed slowly out of the tip of her dick. SARAH (CONT'D) Quick! Lick it gently. I followed Sarah's instructions without hesitation, catching the pre-cum juices on the tip of my tongue. More oozed out. I put the tip of my tongue right on her urethra opening as another glob of the clear syrup escaped. It coated my tongue and rolled around my mouth. The taste was salty and like nothing I had ever experienced before. SARAH (CONT'D) Good. Now lick around the folds. I did. Maxine squirmed and moaned clutching a handful of my hair as I trailed my tongue along the fold where her cock's head connected to the shaft. It was strange hearing a woman make the same sounds I make right before ejaculation. I could tell she was ready to come. SARAH (CONT'D) Now slowly let it slide into your mouth. I parted my lips and let the head of her pole slide into my face. Sarah's voice went stern. SARAH (CONT'D) Careful about your teeth. I opened my jaw as much as I could while still keeping my lips pressed on the skin of the penis. I developed a new level of respect for anyone who had ever given a blow job. The head of Maxine's penis was barely past my lips and I could already feel the tip pressing on my throat. Her cock was rock hard, and I loved the way felt to have a penis in my mouth. It was wonderful and I loved it. SARAH (CONT'D) Now pretend it's a straw and suck it as hard as you can. I did and Maxine let out a loud moan. I swallowed the saliva building in my mouth and sucked even harder. Maxine's moans grew louder and then it happened. Cum filled my mouth so fast, that I felt like I was drowning. Her penis popped from my lips as an explosion of cum poured over my chin and splattered my chest. Another huge blast of cum erupted from her cock and filled my open mouth before I could close it. I instinctively sprang back just as a third shot hit the left side of my nose and poured down my cheek. Another small squirt of sperm missed my face and spread across my neck. Sarah couldn't control her laughter as Maxine's enormous penis shrank slightly and continued to ooze hot white cum. She looked down at me with concern, my face covered in the creamy white of her orgasm. The smell of her cum was strong. The taste was bitter, salty and stronger than the smell. I could feel wet tickles as it dripping slowly down my face. I smiled and licked my lips. Sarah was still giggling so I took the initiative to move forward on my own. Maxine's penis was still dripping cum and still slowly shrinking. I wrapped My lips around it and took as much of it into my mouth as could. She took a deep breath planted both hands on the back of my head. MAXINE Gently. I listened to her and let her soft cock roll around my tongue. I sucked it as softly as I could, and gently pinned it to the roof of my mouth. The feeling of her warm smooth flesh growing in my mouth made my own penis dance around inside my pants. I loved every minute of this so much more than I could have imagined. SARAH You are so, my hero. She dropped to her knees next to me and I felt her tongue on my cheek. Maxine's penis began to grow again while Sarah licked cum from my face. She moved around to the other side as Maxine's cock grew larger than I could handle and I let it out. Sarah grabbed it firmly at the base, the span of her hand not even half the length of the shaft. She stuffed the mushrooming head of the penis into her mouth and rolled it around until spit dripped from her lips, then she began swallowing. I watched with amazement as she took more and more of the cock into her face. She moved her hand from the shaft and took the full length of the penis in. Her lips went al the way to the base of the shaft and she started to gag slightly. She held her face there a minute, then pulled slowly back to half of Maxine's long rod, then began swallowing it again. The giant cock slid from her mouth wet and throbbing. Her saliva dripped from it. A trail connected between the head of the penis and her lips as she pointed the monster toward my face. I sucked on the head again as Sarah stroked the shaft hard. SARAH (CONT'D) I want this in my pussy, now! She stood up and took off her tight pink pants. As I stood, she jumped on the bed and rolled to her back, tossing her legs up and spreading them wide. Maxine put a hand on my cheek and looked me in the eyes. Her eyes were the most beautiful deep shade of green I had ever seen. She stroked my cheek and I felt her start caressing my cock. MAXINE So, this is your first anal experience, isn't it. I shyly nodded. MAXINE (CONT'D) Well, since we don't have any lube, I'm going to give a quick pointer. She unbuttoned my jeans as she continued. MAXINE (CONT'D) You've got a relatively large cock, so you're going to have to get my ass all kinds of slippery before you stick your dick in it. She slid my pants down my legs and dropped to her knees to take them off of me. Sarah was behind her on the bed, one arm propping her up, while the other hand stroked feverishly at her clitoris. Maxine licked my cock teasingly as she raised. I shuddered with pleasure at the feel of her tongue as it tickled my skin. She smiled and kissed me. MAXINE (CONT'D) Regular spit dries too fast, so we're going to need some of the thick saliva that coats your throat. Are you ready? Sure, I said, not really expecting what happened next. She put a hand up to my lips and playfully slipped two fingers into my mouth delicately rubbing my tongue. MAXINE (CONT'D) Don't freak out and bite me, now. She pushed her finger into my throat. It tickled and I gaged slightly as she wriggled them. She pulled them slowly out and they were covered with thick white saliva. She kissed me on the lips again while she spread my throat juice up and down her cock until it glistened. MAXINE (CONT'D) You're going to have to do that yourself when you're behind me. Are you ready? She climbed on to the bed and positioned her self between Sarah's waiting, spread thighs. She rolled her hips letting her penis glide across her wet labia and Sarah squeaked with excitement. On her hands and knees over Sarah, Maxine arched her back and stuck her ass as high into the air as she could while I positioned my self behind her. I lined my hips up with hers, and put two fingers in my mouth. Both women were breathing heavily and Sarah's hands moved all over Maxine's body. I slid two fingers deep into my throat and scooped a big glob of thick saliva. Maxine rocked her hips towards me as I touched the tight little hole in the center of her spread ass cheeks. It was true that this was my first anal experience with another person, but since I'm confessing all of this anyway, I should tell you that I was no stranger to Solo dildo play. I had used saliva to lube my own ass for a toy in this manner on more than one occasion. I moved my fingers in a tiny circular motion around her hole. Watching as some of the saliva dripped down her large testicles, I couldn't believe this was happening. When my middle finger slowly entered her, she moaned quietly and gave a "yeah". I slid my finger slowly further into her ass until half the digit was in. Her tiny hole squeezed my finger like a clamp. I worked it slowly in and out, her ass relaxing as it became more slippery. I slid another finger into her, and she held her breathe as I spread her ass-hole open. With my free hand I tickled my throat again and this time spread the gooey fluids over my own penis until it was nice and slick. I touched the head of my penis to her hole and moved my hips with hers as she slowly pushed her own penis into Sarah's vagina. Sarah hands gripped at the blanket as Maxine's giant cock spread her pussy open. I carefully started driving my own penis into Maxine's tight, wet ass. She tensed and relaxed, then tensed again, squeezing my penis so hard, I thought it might pop like a balloon. More than half my shaft was inside her and it took everything I had in me not to cum. I knew I wasn't going to last long and I began to get a little nervous. I slowly pulled my shaft out until I saw the start of my head, then pushed my cock slowly deeper into her. She did the same to Sarah's pussy and we were all moaning. It took us some time to find a rhythm, but there we were; me on my knees thrusting my hips, watching my penis drive in and out of Maxine's pale round ass, amplifying her own thrusts as she pounded sixteen inches of flesh in and out of my best friends pussy. We had only just started, but I couldn't stop it. I slammed my hips into Maxine's, driving and pinning her cock as far into Sarah as it could go. Sarah screamed with pleasure as my cock exploded. Maxine's ass clinched down around my cock like a vice and I came even harder. SARAH Oh God! Don't Stop! I hadn't realized I had stopped moving. I started moving my hips again, desperate to find a rhythm as I felt my cock still shooting cum inside Maxine. White cream squirted from her ass as I pulled and pushed my penis in and out of her. I couldn't stop I felt my penis squirt again, but I was so excited and horny and full of adrenaline that my erection never wavered. I breathed in deep and relaxed a little as my cock finally stopped erupting. Cum covered my shaft and Maxine's ass as I began pounding my cock into her again. Sarah cried out in ecstacy as her pussy was pounded over and over again. She came and fluid gushed from the lips her pussy every time Maxine and I thrusted. Finally, Maxine came. She thrust into Sarah so hard and fast that I couldn't follow her hips and my penis popped from her ass with squirts of leftover cum following. The two of them panted and moaned as Maxine slammed her hips into Sarah again and held them there. Sarah's legs squeezed the both of us, and I could feel the heels of her feet pressing into the small of my back. Then her whole body went limp. Maxine pulled her penis out of Sarah, and cum dripped from the both of them. Maxine lay between us, and we all panted with pleasure, cum soaking into the bed covers beneath us. I was still hard, and I stroked my cock slowly. The two ladies both grabbed my penis. It was still slippery and shining wet. They squeezed and stroked and tickled my cock until it erupted again. A small shot of cum spurted out and spread across their fingers. We stayed in bed for a while, before Sarah and I parted Maxine's company. . The drive back to Sarah's house was quiet. The radio played low and when we looked at each other, we just smiled, not really needing to say anything. Half way home, I made the mistake of asking her about the Olympics. She was going, and I couldn't understand why she was upset about that. She sighed and looked out the window. SARAH (CONT'D) I'm twenty seven years old. It took more than ten years for me to make alternate. Do I want to lose another ten years of my life to this? I didn't have an answer. I sat in silence as she stared out the window until I apologized. She didn't look back, and I wondered if I had just ruined the whole night. She grabbed my hand. She was still looking out the window, but she wrapped both of her hands around mine and held it tight the rest of the way home. When I pulled into her driveway, she looked at me and softly said the two words that started the change in our relationship. SARAH (CONT'D) Please stay. End...
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