The Business Trip free porn video

The following story is a work of fiction. It contains sexual themes and descriptions. It includes Transgender themes and depictions of Bondage, Domination and Submission. It is meant purely for entertainment and no endorsement or condemnation of the subjects is implied or intended. IF YOU ARE BOTHERED, REPULSED OR OTHERWISE OFFENDED BY THIS SUBJECT MATTER DO NOT READ THIS STORY. The Business Trip (A new story by Bootlover) It all started routinely, as it so often does. Fly out to California to see a client and to meet at my company's home office for a sales meeting. My company's headquarters were in Silicon Valley just south of San Francisco. I was to fly to LA to meet the client and then on up to San Jose for the sales meeting. Sitting on the plane to LA I was dozing and thinking how bored I was with all of this. Flying used to be a cool thing, something you did rarely. Now I was on a plane every few weeks. With the general level of annoyance associated with getting to the airport, toting a bag to the plane, being cramped in a too small seat in a completely full plane and arriving tired to another generic hotel room travel now no had glamour for me. So I looked like any one of a bunch of blas?, bored from the neck up business travelers. Business travel is dull. Except for the few hours leading up to and including the meetings with clients or coworkers there is not a lot to do. You keep up with your work as best you can incorporating the time differences (if that's a factor) and then you generally eat alone, often in the room watching ESPN or HBO. In short it's not that interesting and certainly not much fun. While in LA I had two nights to deal with, the first night I arrived and the second night after my first round of meetings. I spent the first night having a steak and a beer in my room. I watched HBO's Real Sex, jerked off and went to sleep. My meetings went very well at the client's the next day. I was pretty up afterward since a successful meeting would mean a pretty sweet deal for my company and for me financially. That night I was a bit wired. I prepped for the call with the President of the company the next day and then couldn't figure out what to do. I hopped in my rental car and cruised Sunset Strip. Out of curiosity and boredom I visited the Hustler store. Basically a high end sex toy and video store that used the Hustler name to sell the same Jenna Jameson videos, skin mags and silicone dildos that any of a thousand other brightly lit or dark and dingy sex shops had to offer. As I rolled on further in my car I passed Frederick's of Hollywood. Now who wouldn't want to visit the legend? I mean I'd seen their catalogue, visited their website why not complete the trifecta and visit the store? Basically you could say that I started cross dressing as a young teen, sneaking my mother's nylons and other things into my room for a try. I'd get hard even thinking about it (what teenage boy doesn't get hard at the slightest thought of sex?) try on something of hers, jerk off enjoying the feeling of nylon or something and then clean up. I bought my first pair of women's shoes (a pair of extremely cheap plastic slides) at a bargin outlet at age 17. I'm not sure but they may have been found by my parents. We never discussed it if they did. I bought my own nylons from time to time but nothing more than that. I "purged", if that's what you call throwing away one or two things, many times. In college I had a girlfriend and while I tried on a few of her things, without her knowledge, once or twice that was it. For the rest of my life to now I've dabbled a little but never been really "into" dressing. I've had many a fantasy and I frequent CD/TV/TG chat rooms on a regular basis, generally declaring myself to be "str8" but always curious. I've shot gallons of spunk at my computer looking at images of sexy trannies, sub sissies and not so sexy "gurls" in feminine attire. That night at Frederick's the urge came over me again. I had to feel that old eroticism that female accoutrements can bring. I bought a black lace garter belt, some expensive black stockings and a pair of 5" spike black patent pumps. My cock was rock hard the whole time. The clerk who rang up the sale made not comments, no judgments and no small talk trying to pretend these were for my wife. Not many women wear size 11. I raced back to the hotel, stripped and put on my new purchases. Precum was oozing from my cock as I slipped on the nylons and attached them to the garters. I strutted in font of the mirror, teased my nips a little and watched a thin line of cum stretch from my cock like the web from a spider's tail. I stroked and shot a huge load into a towel. I slept in my nylons and garter. I woke up hard the next morning, repeated the process and then went on to my meeting. The meeting went very well and I was in a good mood as I headed to LAX for the jump to San Fran. My new purchases were tucked in my carry on above my head. I landed, got my car and headed for the office. I met with our VP of Sales who told me the client in LA had called and had placed an order even bigger than I had anticipated. The VP was very happy. I was very happy; this order put me well over quota and meant a nice, fat commission check. The VP also told me I had earned a bonus and handed me a check right there! It was several thousand dollars, I was floored. "Have some fun with it" he said. I was in SF for four nights altogether and tonight was a dead night as the sales meeting didn't start until tomorrow. In San Francisco, on a rather main street on the south side of the city is a club I had heard about called Power Exchange. Upstairs was mainly a gay leather club but downstairs was a BDSM club that catered to all. Generally things get started late here and on any given night you can find Doms and Dommes, subbies of all varieties, T-Gurls in full dress and many vanillas taking a walk on the wild side. Generally I fell into the last category. On my only other visit here I wore jeans and a golf shirt and wandered around the place checking out the various side rooms and alcoves and noting all of the condoms and lube strategically placed about. The place had two floors, one basically at street level with a juice bar and coat check and a basement level. Guys watched porn in one room and some had their cocks in their hands. A woman was cuffed to a horse behind a chain link fence while her Dom played her with a tawse and electric toys. An androgynous being in some leather squatted on a bench and jerked off furiously while watching. Several Ts wandered the basement and I watched a line form as one non-passable in a black wig and black PVC dress sucked off anyone who wanted. Not a bad place if one wanted to stem off boredom! It was way too early to go to the club so I meandered down to San Jose and the Pierre Silber store. I shopped for a while and was overwhelmed by the array of fun and erotic footwear, clothes and toys. Like the Hustler store in LA it was clean and open about what it was. I had visited their website so often I felt like I had been there before. I was so jangled over being there, my newfound riches and my plans for the night I was paralyzed and couldn't decide what to buy. I left and went back to my hotel. I took a swim in the pool to relax and stretch out a bit. I ate and then decided to nap. I woke and headed to the city. I cruised around a while. It was still too early to head to the club. On a side street past O'Farrell and the Mitchell Brothers Theater I saw an interesting sign. Leather Specialties stated the sign in neon and the window proclaimed "Clothing, Footwear and more!" I was drawn to it. I parked and walked toward the storefront. The windows contained no display and I noticed that they were concealed by a leather curtain! A small sign in the lower corner said Open and I noted that the hours were from 4:30PM to 1AM. Interesting hours! I have always loved leather. The smell, the feel, the look all get to me. I especially like seeing it on others but I have always preferred women's leather to men's. Women's leather pants are significantly sexier than men's. Likewise women's gloves, boots, and jackets all have nicer cuts, looks and feel than their counterparts for males. I pulled open the door and was immediately immersed in the sweet, overwhelming smell of leather. I closed my eyes and inhaled deeply. The aroma was wonderful and I drank it in. "Good evening to you, Sir." came a male voice. "I can see already that you are a leather connoisseur. The true lover of leather stops to appreciate it, as you have done. Welcome to my store." My greeter was of average height, well groomed and wore men's leather pants, men's leather boots and a shirt with a leather vest. He was not immediately identifiable as gay or straight, Dom or sub and I sensed that he might be all, depending on the situation. "My name is Evan, please enjoy your visit here. If I may be of assistance please ask, until then I will leave you to yourself." This was a person who knew what he was doing. He sized up his customer quickly, did not pressure him and allowed the sale to occur. He knew, probably better than I that I would be a buyer tonight. The remaining questions were what and what quantity of purchases would be made. I roamed the store without purpose until in noticed that I was spending most of my time in the women's section. I began to select things to try on. First was a pair of Italian leather pants. Buttery soft and smooth I could not resist. As I searched the rack silently Evan appeared, as if from the leather itself and offered a pair to me. "I'll hold these as you continue to decide." he said. Next a skirt from the same maker and again Evan proffered a choice. I moved next to the shoe department and selected a pair of Nine West calf boots. The heels were 4" stacked and they zipped up the inside. "Perfect for under your pants." Evan said quietly, "I'll bring a pair to the dressing room." My hands roamed over a pair of crotch high 5" spike heel boots, but I sighed and moved on. I passed a coat rack and found a lambskin blazer that I liked. I didn't even look or wait for Evan, I knew he would have one for me. Finally, at the accessories display I found a pair of wrist length and a pair of shoulder length gloves. As I headed for the dressing room I impulsively reached out and added a leather garter belt to my choices. In the dressing room I stripped and prepared to try on the items. My cock was raging and I was struggling with how to contain it when I saw that Evan had also supplied a pair of black nylon bikini underwear. Tucking my prick between my thighs and cheeks, held snugly there by the smooth nylon my only concern was whether my precum would stain my leather pants. Evan was amazing, each item fit perfectly and I loved the feel of the new skins on my body. While trying on the skirt I realized that the calf boots did not look right, especially with my hairy legs. Faced with the choice of removing the hair or covering them I was torn when a box slid under the dressing room door. Evan had supplied the crotch high boots in my size! My cock threatened to burst through the nylon under my leather skirt as I placed my foot in the boot and zipped it to my knee. I did the same with the other and then took hold of both zippers. I zipped each boot at the same time all the way to my crotch. The boots were tight to my legs and felt fabulous. I almost came in my bikini right there. As I was paying for my purchases at the counter Evan handed me a small bag. "I took the liberty of adding a top to wear with the pants and skirt with my compliments Sir. Thank you for your custom." "Thank you for your very capable assistance." I said as I turned to leave. To my surprise I had spent more than an hour in the store. It was getting late enough for things to be starting at Power Exchange. Still looking as vanilla as can be in a pair of khakis and golf shirt I walked to the front door, paid my cover, had my hand stamped and went in. I was given the once over by a few people in the foyer, most of them gays headed upstairs and I took no note of any reaction as I turned left into the lower club. The juice bar had two patrons on stools and a few people at tables, mostly singles except for a man and a woman together at a middle table. She was in a flowing skirt and loose fitting gauze top, he was in jeans and a T-shirt. Tourists or players I could not tell. As I toured the first floor there were several trannies already here and one in particular looked very sexy. In a pair of clear plastic 5" spike slides, beautifully waxed long legs, a fuchsia mini skirt and tight tank top with either breast forms or implants beneath. Her body was lovely. She had long hair to her shoulders and very well done make up. Her huge black lashes hid her eyes as she slowly sipped a drink through a straw, her long nailed fingers holding the straw. Boing! Mr. Pleasure pistol was awake. I have never had a real time encounter of any kind with another XY chromosome individual. As I said, my fantasy life is very ripe. But looking at this sexy gurl brought many of those fantasies to mind and certainly to cock! I moved downstairs where very little was happening. Other vanillas were roaming like I. The video room had a few seated watchers. A few of the rooms toward the back had someone in them, but only one and little discernable activity. The main room was empty except for the strollers. The various scene areas (a bedroom, a doctor's office, the area behind the chain link fence, the military type room) were all unclaimed and uninhabited. My plan had been to go to the club, get horned up, go back to my hotel try on some of my new purchases and jerk off. If I felt extra bold I might, repeat might change into my new leather pants and calf high boots to meander around the club. Back upstairs the sexy T was no longer in sight. I ordered an orange juice and sat at a table to watch. Slowly over the course of the next hour more patrons arrived. At least 40% of them were T-gurls, 40 percent of them were bi/gay guys and around 20 percent GGs. The bi/gay guys drifted back and forth between Power Exchange and upstairs. I saw more than a few guys arrive with a bag (a gym bag, a shopping bag) and disappear into the men's room. They came out dressed en femme and checked their bag. I began to think more about the bags in my car. Around midnight there was close to 75 people in the club. In no way was it crowded but it no longer appeared empty. I rose from my seat and walked to the door. I had my hand re-stamped and went out to my car. I arranged a few things into one bag, went back to the club and straight to the men's room. There were no urinals in this men's room! 7 large stalls (about the size of a handicap stall) with partitions that began about 2 inches above the floor and ran about eight feet high lined one wall. I heard the unmistakable sound of high heels on the tile floor. I went to an open stall, closed the door behind me and opened my bag, which I hung on a hook. I stripped to my bikinis, slipped my cock over the band and pissed in the toilet. I then replaced my prick in its nest and pulled out the leather pants. Evan had provided me with a white silk shirt. Not a blouse but certainly not a button down collar either. Not some ruffled pirates shirt, just a plain white silk shirt. I smoothed the tails into my leather pants and buttoned and zipped up. I removed the Nine West boots and slipped them on, the shafts fitting perfectly under my pants. Again the nylon of my bikinis was tested. I removed the final items from my bag and placed my drab clothes inside. I pulled on the short gloves which fit under the cuffs of my shirt and then donned the leather blazer. I opened the stall door and stepped out, my own heels now clicking on the tiles. My heart was pounding and my cock throbbing. I selected one of the several full length mirrors and checked out my look. I presented an interesting picture. Clearly I was male. My haircut the standard "business man's regular", my face with no makeup or adornment. My size and build also indicating my maleness. Yet I wore high heel boots that were clearly women's and my clothing was certainly not from Brooks Brothers. I would not say I was androgynous but I certainly presented a confusing set of signals. I did not really care. I was too high from my first venture into public or would this special setting be better described as "semi-public" or "limited showing"? With a deep breath I pushed open the door and stepped out into the hall, crossed over to the coat check and extended my bag. In return I received an embroidered silk square that had the number 14 on it. I slipped it into my front pocket as the checker said, "Enjoy your evening." No Ma'am, Sir, Miss or buddy attached. I walked carefully but with no real difficulty to the stairs and headed for the basement. Things had definitely livened up here. Behind the chain link the couple I first noticed at the tables was prepping. He laying out some toys and implements from a large black doctor's bag, she naked and huddled on a bench. In the "bedroom" two women were lying on the bed kissing and an audience of 15 people or so watched from behind a rope. I joined the viewers and as one girl stripped the other. The now nude girl was tattooed in many places including her neck, back, ankles, biceps, breasts and belly. She was pierced in the eyebrow, tongue, belly button, labia and had barbells through each nipple. Not my preferred style but I watched as her companion kissed her deeply and toyed with her pierced nips. She tugged and twisted causing the tattooed girl to writhe on the bed, all the while never allowing their kiss to be broken. Suddenly I felt a hand on my ass! I turned to see a dark haired man with a heavy beard leer a smile at me as he rubbed my cheeks. "Not my thing." I said as I removed his hand. "Sorry. I just thought..." He said. "Not me, try someone else." A sissy in pink next to me giggled. I moved on from the two girls and walked through the military area where a female of some sort (T or GG I could not tell in the dark) waited on a cot. The back rooms (more like cubicles actually) were now mostly occupied. In one two males were in varying states of undress and exploring each other. In another I saw a man licking the spike heels of an unknown wearer. Another held a blonde T on her knees sucking the condomed cock of a guy in a business suit. As I finished the loop and ended up at the chain link show area the naked woman was now standing, head bowed and hands at her side as her Master played with her back with a fur mitten and a short whip. Her face winced from time to time as the little whip struck but she did not cry out. The mitten reached around and massaged her large, hanging breasts. Her nipples were very hard and obviously responding to the touch. The Master made eye contact with me as he worked. "What are you?" he asked. "I am a cow." the woman replied. She was plump but not obese. I watched to see what this play was about. "What do cows do?" asked the Master. "Give milk from their udders." she replied. With bare hands he reached around her and squeezed both of her big tits very hard. "What are these?" "Those are my udders, Sir." He moved in front of her and grasped each nipple between his thumb and finger. He lifted her boobs, by the nipple, until the nips were about at the level of her nose and bearing the full weight of those large glands. Small tears worked down her face but she did not make a sound. He released her nipples and her breasts slapped to her rib cage. She took a deep breath, sucking in air sharply. Her nipples were very red and very swollen. The Master looked at me. "Want to suck?" he said, indicating her tits. A felt a weird smile cross my face. "Sure." He opened the gate in the chain link and invited me in. I sat on a bench and he pushed her toward me. "Please, will you drink from Mama Cow's udder?" she asked me as she lifted her breasts and offered them to me. My cock was harder than her engorged nipples, and believe me they were hard. I slipped my lips over one nipple and began to suckle. She drew in a short breath again, I can only imagine what level of pain she might have been in. The Master whispered in my ear. "Suck as hard as you like, as long as you like. She is trained to allow you to get your pleasure." I have never sucked a nipple like this. Usually the level of pain from this will cause a woman to make me stop. I sucked as I had always wanted to suck. After a few minutes I was getting so horny that I had to stop. I assumed (and rightly so) that I wasn't going to get off in or from this scene. I stood and left the cage and the master invited another in to suck the other nip. My head was swimming and I needed a minute. I went upstairs, got a soda and drank it quickly. I then moved across the floor to a quiet area with soft light in a corner. I sat there for a moment, my legs crossed just enjoying the experience of being in my leather and boots and remembering the feel of that nipple in my mouth. A sensation I could not place worked its way into my consciousness. I opened my eyes to see the sissy boy licking my boots! Now this was different! The sissy was in a pink ruffled dress with white stockings, white lacy anklets and white spike heel platforms. She also had on white satin gloves and a red wig. I would guess this sissy was about 50ish. She was not passable or pretty by any stretch but she was earnest. In her frilly satin and ruffles as she knelt and licked my black leather boots as I sat above her in my black leather pants and jacket. We were a real juxtaposition. She looked up at me and in a squeaky attempt at a femme voice said, "May I?" "Knock yourself out sissy, until I tire of it." She returned to licking, I re-crossed my legs and she went to work on the other boot. I felt a sense of power I had not experienced before. Oddly my cock grew hard again. I looked up from this little girly lapping my boots to see the gurl from earlier this evening standing in front of me. She looked just as lovely as before. Her toes were painted the same color as her skirt. Her legs were so smooth they could have been marble and the mini skirt barely covered the tops of her thighs. Her waist was narrow and I even wondered if she had had a set of ribs removed. Her face was beautifully made up and up close she looked very femme and very pretty. Her eyes were striking green, I expect from contacts and her lips were very full and a wet, luscious red. This was a gurl who took her femininity very seriously. "I could lick something that would make you feel better than that." she offered in a whisper and with a sexy smile. "I'm all for that." I replied and looked down. "That's enough you prissy bitch. If I want more of your boot licking I'll let you know." The sissy ran away in tears, as much, I assume, from knowing it was the right reaction for her role as from the feeling of rejection. I stood. "My name is Tanya." this beauty said and extended her hand. I took her hand and hesitated. Should I kiss it? Take it and lead her to a more secluded area? What? Was I in male mode with a female? Was I a gurl in gurl's clothes off for a lesbian experience? How do I handle this? In the end I kissed her hand. She was very tall. Even in my 4" heels she was a good 2-3" taller than me. I then did what I felt. I slipped my arm around her waist and we walked together to the stairs. She separated and descended before me, daintily holding my hand as I followed behind her so that I could steady her. Once on level ground again she moved back to my side, I re-circled her waist and she let her hand rest ever so lightly on my shoulder. While still confused about myself I had no doubt that I was with a feminine person. We received more than a few stares as we walked the length of the basement heading for the back. Along the back wall we found an open cubby and moved in. "Please sit, lover." she whispered and moved me to the bench built again the wall. I sat facing her and she straddled my leather thighs and lowered her body onto my legs. She was quite light. I took off my gloves, laid them on the bench and ran my hands over her smooth, smooth legs. She reached for them and brought them to her face. She inhaled and whispered, "I love the smell of human skin with leather on it." She closed her eyes and breathed again and I could feel the air wafting about my fingers as she did so. She released my hands and they automatically returned to her legs, gently caressing them. She wrapped her arms around my neck and leaned in to me. I could smell her perfume now. Were those luscious red lips about to touch mine? Would this be my first kiss all over again? She teased me. Never letting her lips touch me. She did not speak, only let her breath play on my face, my ear, my neck. My cock could not be any harder. I wondered what her clit was doing. Her hands slipped from my neck and she ran them under my jacket and across my silken chest. "Your leather is so beautiful." she breathed into my ear. Her nails teased my nipples. "Please let me have you." I heard her say and I looked into her eyes saw a look of lust. "I'm all yours." She laid me back on the bench and knelt between my legs. She unbuttoned and unzipped my pants, pulling them to my thighs and then my underwear followed. My cock sprang straight up and she smiled. She stroked it deftly and her hands were as soft any skin I had ever felt. I would have cum right there if she had not pressed her thumb nail into the base of my shaft blocking the tube that leads from my balls causing a small bit of pain. The pain came less from her nail and more from being denied release at so exact a point. My cock wilted a bit from the pain and she smiled again. She opened a condom and slipped it on me. Then her head lowered and her lips surrounded the head. The pleasure was immense and my cock immediately regained it's rigidity. She gently played with my balls as she held me in her mouth. Then she began to blow me in earnest and bobbed her head up and down on my dick. I came very quickly, I had been aroused and titillated for so long I could not last long at all. She deftly removed the rubber, with most of my jizz in the tip. She pulled a paper towel from a dispenser above, wiped me clean and pulled up my bikini. She stood to throw away the waste and I stood to fix my shirt and pants. "Don't leave." I asked. "What about you?" She pushed me back onto the bench so that I was sitting against the wall with my legs straight out the length of the bench. She peeled off her skirt and her top. Her breasts were expensive and beautifully formed for her body. Her hips were extremely female and the thong panty looked like it was being worn by a VS model. She sat backward between my thighs, rubbing her sweet ass into my crotch as she handed me my gloves. "Wrap me in your leather." she breathed. I put my gloves on, wrapped my arms and legs around her nearly naked body and heard her sigh in pleasure. "Just hold me a minute. I rarely cum because of the hormones." she said "But I can enjoy stimulation." I cupped her breasts in my gloved hands and clenched her tighter with my legs. Her hair was in my face and her perfumed danced under my nose. She pulled her panty aside and began to stroke her soft clit. My reaction was instinctive. I was holding onto this feminine body, I felt male even in my female clothes and boots. Without thinking I leaned in and kissed her on the neck. She stiffened in my hold for a minute and then turned and looked at me with questioning eyes. I said nothing and kissed her cheek. She laid her head back on my shoulder and began to moan very lightly. Her moans rose each time I kissed her cheek, her jaw line, her neck. She shuddered a bit in my arms and then pulled her panty back into place. She curled up on her side a bit, staying in my arms and legs and nuzzling her face into my neck. "Thank you." she whispered and I felt a tear on my neck. "For what?" I asked. "For making me feel like a woman." she replied. "You are a woman, sweetie, you are." We stayed with me holding her for long minutes more. Then she stood. "I need to powder my nose. Meet me upstairs in a few minutes?" "Of course." I sat there for a few minutes, confused. Where was I in all this? This was pure sex, that was for sure but it was something more. It was the first time I had sex with, with, with... Tanya was a woman in every way except two. And both of those were due to genetics, nothing more. The sissy upstairs was a guy in a dress. Always will be. Tanya wasn't. But where did that leave me? I walked upstairs still confused. Tanya was waiting, her makeup touched up, looking as beautiful as ever. "You know," she said, "it's 2:30. A girl's gotta get her sleep." "You ditching me?" I asked. "If I were ditching you I'd be gone already. Meet me here again tomorrow night?" "Absolutely!" I replied. She leaned in and gave me a kiss on the cheek. "See you then, lover."