The following fictional tale contains description of Male/TS sex. If this is not your preference or you are underage please move on. Otherwise enjoy.
Allow me to introduce myself, my name is Alexander, Al for short. I'm thirty seven years old, in moderately decent shape and the product of a moderately conservative white suburban upbringing. Despite that I approach life with a live and let live attitude and I try to first understand before I decide to accept or reject a particular idea or situation. The trail that led to this particular point in my life consisted of several independent but overlapping occurrences. Firstly, the woman with whom I had be enjoying a lengthy but non matrimonial relationship stated one day that she needed to take a new journey in her life and I was not the preferred traveling companion. She was packed and out of the house the following morning. Two weeks after this particular body blow came the announcement that the small company that I was working for had been purchased by a large multi national and that changes were coming. The first change was a complete sweep of the management chain. A new leadership team appeared and proceeded to turn the place upside down. We were reorganized, right sized, and re-engineered and in the process more than half the original workforce was gone and I found myself gazing out at a new and foreign landscape. After six months of struggling through the new way of doing business and trying to get my little department on the right, read new, track I was approached by the new general manager. Oh, I forget to mention, when my boss was canned they told me to take charge of things until the new organization was in place. I was still doing that when I was called into the GMs office.
She shook my hand and asked me to sit down. She proceeded to tell me that I had done a great job keeping things going with all the chaos swirling around us and had the only department that hadn't fallen behind in making the new system work. Apparently I had managed to impress them with the way I was feverishly treading water to keep from drowning. She then told me that I was to be offered a promotion opportunity in one of the other company divisions and she strongly suggested I take it. Apparently in the new company if you didn't want to go up, you went out. I sat and thought about what was going on out there, and what had been happening in my personal life and decided to take the offer and see if a change of pace and place might be good for me. I listed my house with a broker, had a sale to get rid of all the furnishings etc and headed for my new location with just a few bags. The company helped me locate an apartment in a relatively quiet section of the city that was once an industrial district but had been undergoing extensive redevelopment into apartment buildings, shopping and some recreation facilities. It wasn't too bad.
My new job was time consuming in the beginning as I had a whole new aspect of the business to learn but since I was promoted more for my leadership and organizational skills I was able to get my hands around it fairly fast and progress was soon evident. This resulted in some more free time so I was able to divide it amongst my favorite leisure activities, reading, hunting for books and walking. I always preferred small bookshops to the big mega chain stores and the one big benefit of being in a city environment is the likelihood of finding those quaint out of the way shops and I would be out each weekend walking around looking for them. It was in one of those shops that this tale really begins. It was several months after I reported for duty, and it was one of my first free Saturdays since coming here. Now the obvious thing you might say is to sit and look through the phone book and find these places and head straight for them, but where is the fun in that. No, I prefer to wander about looking for these treasure troves and knowing I have a spare twenty in my shoe with my new address written on it in case I get lost and need a cab ride home. So it was on sunny Saturday morning that after a couple of hours of walking in the area not to far from home, I came across "The Book Shop". It wasn't a very clever name but it certainly covered it all. I opened the door and heard the faint jingle of an old time door bell, as in real bell. "Cool" I thought. It smelled like a book store should, with heavy traces of old leather and paper, and no scented candles or any of that other claptrap the new places have.
It was reasonably well lit, with dark wooden bookshelves and some furniture pieces. There were a couple of other customers wandering amongst the shelving and I began to join them when I heard a soft voice,
"Welcome to the Shop, is there anything I can help you with."
I turned around to tell the clerk I was just going to look around but I never said it. The clerk was a very interesting looking woman in her early thirties. She was perhaps five feet six, a slender build and delicate facial features. She was also African American, with a smooth mocha complexion and light brown eyes. Her hair was long and straight, which made me think that somewhere in her past was some European ancestry, which was not uncommon for many of the descendants of the forcibly relocated Africans.
She also wore wire frame glasses and was holding an armload of books. Her smile was faint yet still warm and genuine.
"Um, well, I'm new in town and this is my first time here. Do you carry just used books or new as well."
"We have both, although we don't go heavy with all the new ones but if you need a particular title we can get anything in print in twenty four hours. What are you interested in."
"Well, firstly I'm interested in finding a good book shop since I do read a lot but won't have anything to do with the big chains or online stores. As to preferred material I like history, natural science, Sci-Fi and fantasy. I'm not much on modern popular fiction though."
"Me neither," she said with a slightly bigger smile. "We have all of that here. History is along the back, sciences up the right side, the scifi and fantasy third row back in the middle. Please feel free to wander around. Call me if you need anything."
"Thanks, I will."
For the next two hours I wandered up and down the aisles. It wasn't a particularly large place but it was well organized and space was used very well. They really had a lot of material here and I had found several interesting titles before I was through. I approached the counter and noticed the other customers had left. I wasn't aware of any others that may have come or gone but I get like that when I'm hunting. As I put the books on the counter the clerk came around to ring them up. She wrote the titles down in a book and rang up the prices on an old style register. No point of purchase inventory systems here. I was certain I found my new book shop and I said so.
"This place is really great, I'm sure I'll be back in a lot."
"Well thank you, that's nice to hear. I've worked very hard to get it like this. I'm hoping it fills the need for customers like you that are looking for something different." She said the last with another small smile and since no one else was waiting she kept talking. She mentioned that she was not a clerk but the owner. She had always loved to read and loved books and had been working in one book store or another ever since she got her working papers. And she didn't just work, she studied. How the stores were run, set up, what the customers wanted and where things could be found. She asked me if I would like a cup of coffee and I accepted. We sat down in a little reading nook that overlooked the sidewalk and discussed books and bookstores and life in general. I hadn't felt this comfortable in a persons presence in I don't know how long. On several occasions more customers came in and she would bounce up to take care of them but always indicating I didn't need to move along. Before I knew it, it was four in the afternoon and my stomach was rumbling. When I let go with a particularly loud grumble her eyebrows flew up and she giggled.
"Oh my, I'm so sorry. I've kept you here so long you've missed lunch.
You must be starving."
"Oh I'm fine," I lied. I was indeed ready to eat a small cow. "I had a big breakfast."
"Well thank you for that little white lie, but I know better. We close at four thirty on Saturdays. Please let me take you to dinner. If you're new in town your probably don't know all the good eating spots around here."
"I don't know any of them. I hit the Safeway and then make my own meals."
"Not tonight you're not. An early supper for you. I'll start closing up now."
And so it was that at promptly four thirty we were outside the door and the key was turning in the lock. As we walked down the street I thought that we represented a slightly mismatched pair. At six feet two I towered over her. My pale northern European complexion was in stark contrast to her mild brown tone. But who cared. We talked as we walked the four blocks to the restaurant of her choice and before we were half way there she had slipped her arm in mine and we strolled along without a care. Well, my empty stomach cared but that would soon be remedied. The restaurant was not much different than the book shop, smallish, quaint with a friendly inviting atmosphere. It was a combination of Italian and American cuisine served at small round tables with white table clothes. The food was good and reasonably priced and it wasn't long before the grumbles had been laid to rest. We haggled over the check but finally went dutch and as we came outside I asked if she lived nearby. She looked at me with a cocked eyebrow and a slightly bemused smile.
"And why do you ask, good sir?"
"Oh well, it's getting dark and I figured I should walk you home."
"Ah, gallantry. Don't find that so much anymore. I think women's lib has scared guys out of it. But as it happens I live exactly two blocks that way," she pointed down the street, "and it's a very safe neighborhood, but if you would like to accept my invitation for some coffee and desert that would be fine too."
Of course I accepted. To this point I was merely thrilled at having found a great place to find books and a terrific person with which to discuss them. Now however the male mind began to more firmly assert itself and I began to think how long it had been since I had enjoyed someone else physically. I tried not to make too much out of it but it was enticing. So it was that we continued our stroll arm in arm and arrived at a nice brownstone on a tree lined block. I followed her in and we walked up the flight of stairs to her second floor apartment. The building had been renovated and turned into three one story apartments. Hers was spacious and reflected the mind that had created the book shop. She took my coat and told me to sit anywhere while she got the coffee and desert. I sat down on the couch and looked around a bit, trying to hide my nervousness. The comfort I previously felt had slipped a little in the presence of this new possibility.
She came back in with a tray of coffee and small cakes. She poured for us both and then sat down next to me. She was close but we weren't in contact. I picked up my cup and sipped. It was good.
"No cream or sugar," she asked.
"No, didn't you notice it at the shop. I had two cups, straight. I like it black."
"Oh you do, do you?" she smirked a little and then offered me a cake.
I accepted one and took a bite. It was delicious but also very crumbly. A number of them had tried to escape being devoured and wound up down the front of me. My host laughed and said,
"No matter how wonderful the man, they all seem to be a bit sloppy," she laughed and proceeded to brush the crumbs away. Some had fallen on my leg and she brushed those away too. She had leaned a little closer and when she was done she looked at me with those pale brown eyes and said,
"All better now, right?"
I simply nodded and continued to gaze into those eyes when a thought occurred to me.
"I don't even know your name."
She brought her head up closer and said, "It's Violet." Then she leaned in closer and kissed me. Her lips were warm and insistent. Her hand came up the side of my neck and helped pull me closer. Through parted lips our tongues met and did a little dance. I'm not sure how long it lasted but when she pulled back I knew it wasn't nearly long enough. She didn't pull back very far and about all I could see was her eyes and the upper half of her face.
"I need to tell you something," she said softly.
"You can tell me anything you want."
"I didn't think I was going to tell you this so soon, but something is happening here and it's something you need to know." Her eyes tightened a little bit and I was getting a little concerned about what was coming. "There is more to me than meets the eye." She drew deep breath. "I'm a preoperative transsexual."
She didn't look down or away but held her eyes on mine. From that close distance I'm sure she could hear the wheels spinning in my head as I processed this startling revelation. There was nothing about her that could have been a clue. Not a single masculine feature that I could identify. Then I thought about what a great day I had with her so far, how wonderful it had been to discuss books and writers and book stores with her. I came here for a change and this was certainly a big one, so with a mental shrug I let all the tumblers click into place and simply accept what was and go along for the ride and see where it led me. To give her a reply I leaned in and started kissing her again. I could feel her catch her breath a bit, then let it out through her nose. Then she began kissing me back with great enthusiasm, as if a dam had burst and she was free to express her feelings. Her lithe arms went around my neck and her mouth was open and her tongue made serious inroads into my mouth. It was without a doubt the most energetic and passionate kiss I ever had. I put my arms around her and pulled her closer, my hands running over her back. With surprising strength, she sort of gave me a full body shove and we wound up lying on the couch with her on top of me. My hands wandered down her back and caressed her ass, which was firm and rounded. She began to grind her hips into mine and I could feel my cock beginning to really respond. Again this went on for a period of time but how long I wasn't really sure. Eventually we broke our lip lock and she lifted her head up far enough for me to see her whole face. Her eyes were bright and her smile was broad.
"Wait here. I have something special for you."
I bit back the obvious response of `I'm sure you do' and only said,
"I'm not planning on going anywhere anytime soon."
She gave me a smile, slid off and moved quickly out of the room. A door closed down the hall and I sat back up, taking a moment to shift my hardened cock to a more comfortable position. I saw the one clock that was in the room and noticed it was barely seven o'clock. Around seven ten, I heard a door open and a slow clicking come down the hall. I turned and saw what had to be the sexiest `person' ever. It was quite a shock compared to the conservative and demure woman I had first met but I wasn't complaining. She was taller by about five inches thanks to the stiletto heeled straps she wore. Her legs were encased in black nylon thigh high stockings with elastic garters. A black lace bustier covered her mid torso and smallish breasts. Below that was a black satin thong with a hint of a bulge. Her hair was back over her shoulders and hung to about mid way to her butt. She had taken off the glasses, which by the way I love on a woman, but I wasn't going to quibble about details. She walked slowly around to the couch and I stood up. We were about a foot apart. I slipped a hand around her waist and pulled her the rest of the way. With the help of the heels her face was much closer and I only had to bend my neck a bit to get back to those lovely lips. The kissing was just as passionate as before but with much more body involvement now. Our hands were all over each other. I made sure one hand stayed on that magnificent ass, squeezing and fondling the firm and jutting muscles. I also used it to pull her tight enough to me to maintain contact as our hips ground together. Her hands were on my shoulders, my back and my ass. Then I felt them come around and start on my shirt buttons. They were undone in seconds and my shirt was on the floor. Next she went after my belt and then my pants were opened and sliding down my legs. She broke lip contact and slid down my chest and stomach, crouching at my feet to remove my shoes and socks. I pulled off my t-shirt while she let the side of her face rub on my crotch through my boxers. The looking up at me with those now devilish pale brown eyes, she tugged my shorts down and sorted of cooed as my cock bounced into view.
Now I'm no porn star but I will say that I am pretty proportional and at six feet two that works out to about a seven inch cock, fairly meaty with lots of veins and sleek head. My balls hang a little low and are reasonably sized. I stepped out of my shorts and just stood there looking down at her.
She ran her fingers over my shaft and balls, still making little bird noises. Then she licked them and then she kissed them. Then she pulled the shaft down level and let her red wet lips slide over the tip and half way down the shaft. As with her kiss I have never felt a better pair of lips then hers. She began to suck with vigor and I swear my feet began to leave the floor. She varied speed and pressure. Sometimes she would linger at the head and stroke the shaft. Now and again she would push it flat against my stomach and lick the underside and down to my balls. Speaking of balls, mine were beginning to pull up and I knew if I didn't intervene I was going to blow my load far sooner then I wanted to. So with some reluctance I pulled out of her mouth and reached down and pulled her back to standing position. She didn't let go of my cock though and her warm hand continued to send little electric jolts to my spine. I kissed her again and at the same time let my hand do a little exploration of the front of her body. I caressed her small breasts and fingered her hard nipples through the fabric.
She moaned and squirmed and squeezed harder on my cock. I let my hand slide down her stomach and over the shiny black satin front of her thong. The bulge I thought I saw earlier had grown considerably. She continued to moan into my mouth and her hand was now stroking my cock. I slipped my fingers past the waist band pulled the fabric down to free her `surprise'. I felt nice and warm and firm in my hand. I could tell by feel that it wasn't very big but it would be a nice one.
I pulled my mouth off of hers and looked down. As I thought, her cock was hard, the head shiny with some precum. The skin tone was a darker brown and it looked to be about five inches long and maybe four and a half around. I rubbed it and gave it a squeeze. Her breathing was heavy and we looked at each other as we jerked each others cocks. It was at once surreal and the sexiest thing I'd ever done.
"Please baby, let me suck you some more. I love your cock in my mouth."
"Hmm, I was thinking the same thing. Come here."
I moved her over to the couch and lay flat out on my back. I pulled her down so her hips were by my head and her face was right at my cock. She immediately grabbed it and began to suck greedily on it. I continued to play with hers for a bit and then took the plunge. I opened my mouth and let the hard brown flesh enter it. I let my tongue slide over the head because I always loved having that done to me. Her precum was tangy and bit salty. I closed my lips around the shaft and began to suck my first cock. She began to moan and pump her hips a bit. I guess I was doing okay. We continued like this for a while, each enjoying the others oral attention. I squeezed her ass as I pulled her all inside me. I even took the step to finger her little bunghole and this made her squeal around my cock. Soon enough, or perhaps too soon, I felt the inevitable begin to build. My balls were pulling up tightly and my cock was twitching. Her hips moved more urgently so I got the idea she may have been close as well. I began to grunt as I felt that familiar tingle and I felt her clench down harder with her lips and small hands. My first eruption pulled my ass off the couch and drover my cock deeper in her mouth. Before my third shot of cum hit her throat she began to buck and I felt a squirt of warm fluid hit the inside of my cheek and coat my tongue. Several more followed and I resolved to not lose a drop. We rode out our mutual orgasms and then just melted back into each other and the couch. I swallowed what cum had dripped into my throat but left the rest on my tongue. I felt her slide around and climb up on top of me. Her lips clamped down on mine and our tongues met again mixing and sharing our cum. We continued to kiss for a few minutes and then she pulled away and looked at me.
"Hmmmm, that was one for the books. Ready for the next chapter?"
I could only grin in response.
To be continued.