Hose and a Hard-On Ch. 01

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Alex's journey into cross-dressing and bisexuality.
4.3k words
4.56
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22

Part 1 of the 2 part series

Updated 10/25/2022
Created 02/28/2011
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TaraJean
TaraJean
175 Followers

Growing up in the midwest Alex was a good student, popular with both boys and girls. As a kid he was athletic, playing baseball, football and track. When he reached puberty he went through the usual growing pains that other kids went through, but his body never developed enough to continue playing competitive sports. When he stopped growing he was 5' 7" and thin with narrow shoulders and hips. In High School he ran the gamut of dating; taking a girls out just once, multiple dates with one girl, and even a 3-month period with the same girl, but never a long commitment.

In college he joined a Fraternity and dated many women. He was brilliant with computer languages and was recruited by many top software companies. Life couldn't have been going better for Alex.

He graduated from college and set himself up as a freelance consultant. This enabled him to work from home while companies periodically paid for his travel to various cities for meetings or for longer term projects. His sex life was great, he knew how to please a woman and due to his good looks, inner confidence and successful business acumen he had no trouble meeting them.

One night after a particularly enjoyable romp with a beautiful young woman he'd picked up, he found himself staring at the ceiling while she slept next to him. He couldn't remember her name, but that wasn't what concerned him. What was concerning him was why he was starting to wonder what it felt like to BE her. Did she enjoy sex as much as he did? Did she enjoy wearing sexy clothes? What about all the makeup and preparation women went through to "make themselves pretty"? What did it feel like to have sex with a man, not as another man, but as a woman? Alex had never been attracted to men, but he was starting to wonder what women liked about men.

He got out of bed trying to shake these strange thoughts. He was naked as he walked to the sliding glass door and out onto the balcony of his apartment. It was dark and windy, no moon tonight. He looked out at the lights of the city and thought again about the girl asleep on the bed behind him. The wind felt good on his naked body and he started to stroke his 8" shaft. She had worn a small black dress and pantyhose last night. He glanced back and saw the dress hanging on a chair. It felt so good to run a hand up and down the legs of a woman wearing hose. What did it feel like to wear them?

He quietly walked back inside. The girl was sleeping soundly. Alex picked up her dress and pantyhose off the chair and slowly walked into his study and locked the door. Without really thinking about it he sat down on the couch and started to put on the pantyhose. He tried to do it like he had seen women put them on, but he snagged a toe and put a run in one leg. Damn. He finally got them on, stood up and smoothed out the material, running his hands over his legs, ass and penis. Wow, he thought, this feels great! He looked at her dress, wondering if it would fit.

He lifted the dress, holding it up in front of him. He could smell her perfume on it and it made his cock strain against the pantyhose. Lifting it over his head like a T-shirt he put his arms through and let the dress slide down his body. It was a little tight, but it fit! He pulled the dress down over his hips and adjusted it on his body. It felt so sexy! He walked around the room feeling the dress sway and lightly brush his hose-covered ass. His cock was really getting hard now and he needed some release.

He carefully removed the dress and pantyhose and walked back into the bedroom. The girl was still sleeping. She had rolled over onto her stomach, the covers falling away from her body. She had apparently gotten up at some point and put her panties back on. She was a vision lying there. Alex carefully put the dress and hose back on the chair and crept into bed. He moved down to the girls ass and started to rub his face lightly over her panties, breathing in her scent as he did. She moaned. Using just his face and tongue he rubbed and licked all over her ass. In the back of his mind he wondered what it would be like to wear silky panties like these. He carefully rolled her over and proceeded to lick her shaved pussy through the panties. She was getting wet now and was only partially awake. He kept going, burying his face in her sucking on her large clit thoroughly enjoying the feel of her panties on his face. Finally he felt her hands on his head, pulling him into her as, writhing and moaning, she came again and again.

Alex moved up to his pillow and, once again, stared up at the ceiling. The girl rolled over and half-asleep, started playing with his cock as she snuggled against his chest. She started kissing his chest and moved lower and lower, Alex' smile growing wider the lower she went. As she took him into her mouth, Alex couldn't stop thinking how good the feeling of the pantyhose and dress had felt on his body. In only a few moments he was bucking and came in the girl's mouth. She sucked greedily, swallowing as much as she could. He glanced down and saw her wipe some of his cum off of her chin and lick it off her fingers. Her eyes were still closed as she moved back up and put her head on his chest. She was asleep almost immediately.

The next morning, thankfully, she was gone. Nothing, thought Alex, was more awkward than having to small-talk with a girl the morning after. As he cleaned up the bedroom he saw, there in the waste basket, the girl's pantyhose. She must have noticed the run and decided to toss them. Alex pulled them out of the basket and sat on the bed, lifting them to his face he inhaled and could smell her scent again. He let them slip around his fingers, feeling the material. Removing his clothes, he put them on and stood up and continued to clean up the apartment. It felt wonderful to walk around in nothing but the nylons. They felt so good on his body. He expected them to make him warm, but they really didn't, he could feel the air pass through the material and cool his legs. After a while he sat in his leather recliner and started to feel his legs and cock. Stroking himself through the material was really turning him on. He rubbed for a while and then tore a small hole in the underside and pulled his balls through. The material squeezed around his scrotum tightly turning him on even more. As he masturbated he started to fantasize that he was the girl from last night, sucking his cock and really enjoying it. How would it feel to have a hard dick in your mouth? The anticipation, waiting for it to spurt. As the fantasy went on he tore another hole in the hose and pulled his cock out. Stroking faster and faster he imagined a cock in his mouth getting hotter and hotter, swelling, ready to burst. As he came he caught his semen in his hand and quickly brought it to his mouth, slurping it in, rolling it around in his mouth and swallowed. Hmm, he thought, it wasn't too bad, salty and slippery. Feeling a little guilty, Alex took off the pantyhose and tossed them back in the trash can.

All that next week Alex went back and forth in his mind, alternatingly feeling guilty about his new-found feelings and wishing he hadn't thrown out the pantyhose. But work soon took over. He received an offer to go to California for an extended consultancy. The software company would put him up in a 5-star hotel overlooking the ocean for 4 to 6 weeks. The offer was good so he accepted the job, got his affairs in order over the next few days and then headed to the airport.

Going through security was quicker than expected so Alex had plenty of time to wait for his flight to LAX. As he sat at an airport bar sipping a gin and tonic, he noticed an attractive woman at the other end of the bar. She was older than Alex, probably early thirties with large breasts and a thin waist. She had shoulder length brunette hair and was wearing an ankle-length print skirt with sandals and a white blouse. Alex always traveled in an expensive suit giving him the air of a successful businessman. Their eyes met and she smiled seductively. He smiled back and lifted his glass in a toast.

Finishing his drink, he walked out of the bar and towards the restrooms. Seeing that there was a private family restroom available, Alex opened the door and walked in. As the door was closing Alex turned around to see the attractive woman from the bar slip in, close and lock the door. She immediately put a finger to her lips signaling that he shouldn't say a word. She walked over to him, put her arms around him and kissed him passionately. Taken aback, Alex didn't know quite what to do, so he "let her drive". As she was kissing him she slowly removed his suit jacket and hung it on the hook at the door. Looking into his eyes she slowly unbuttoned her blouse, revealing a plain white bra. Alex reached behind her and unclasped the bra letting her large breasts free. Pushing her against the wall, he began licking, sucking and chewing on her protruding nipples. She grabbed the back of his head and pulled him closer. Her hands started unfastening his belt and unbuttoned his slacks. His pants fell down around his ankles and she frantically grabbed at his hardening cock through his boxers. Alex reached behind her, lifting her skirt and started playing with her ass. She had on simple cotton panties. Lifting her legs and wrapping them around Alex' waist, Alex was forced to hold her up by her ass as he pressed her against the wall. "Fuck me" she begged. He managed to drop his boxers and pull the material of her panties aside, away from her dripping pussy. He slid in easily and she gasped. Desperately she began to ride him, moving her hips from side to side, up and down, lifting off his cock almost all the way and then slamming her body back down. Alex could hardly hold on, but using the wall for leverage he pressed against her, mauling her breasts as they fucked.

"I'm close, baby" he muttered,

"Cum inside me" she replied and she started bucking him harder and faster. Alex couldn't hold back any longer, and with a deep thrust he shoved his throbbing cock deep inside her and exploded. He came and came, not believing how much he ejaculated. He pulled out and she collapsed onto the plastic chair in the corner of the restroom. Looking in his eyes she said, "eat me" and spread her legs. She had a full un-trimmed bush and Alex practically dove into her cunt. As his tongue licked her slit she pushed and all his cum came oozing out of her. Alex ate it up, lapping at her dripping cunt and swallowing their combined juices as if he was starving. His cock was still hard, the taste and smell were incredible, it was turning him on so much! Continuing to eat her, he brought the woman to orgasm which released more of her juices into his mouth.

He stood up, his erection now pointing at the woman's face. She leaned forward and slowly licked it clean. She continued to suck, expertly taking him into her mouth. It was one of the best blowjobs he'd ever had. As he was about to cum she stood up and said, "I want you to cum in my panties, I want to feel your cum for the entire flight". She started jerking him with one hand and pulled the front of her panties open with the other. She aimed it and he shot his load into her panties, right onto her pubic hair. She let go of the top of the panties and leaned down and licked the remaining cum off his cock, then turned and started getting dressed. Alex quickly splashed some water on his face, put on his clothes and started to leave the restroom. As he looked back, the woman was cleaning up her face and fixing her hair. She smiled at him then reached into her purse and pulled out a pair of satiny panties. As the door closed, she tossed them to him.

"Wow", he thought as he walked over to the Men's room. Once inside he cleaned up and smiled, thinking about what had just happened. He'd never had totally anonymous sex before, and he'd surely never gone down on a woman after cumming inside her, in fact, he usually used a condom. Eating his own cum from a woman's pussy was unbelievably erotic. He looked at the panties that she had given him, and realized that they were dirty. He lifted them to his face and sniffed in her scent. "Wow" he thought again.

Still smiling, Alex left the Men's room and started walking towards his gate. Glancing over at the waiting area across from the restrooms he noticed the woman he'd just been with. She was holding a little 2-year-old girl in her arms and talking to a little 4-year-old boy standing in front of her. A man, obviously her husband, was sitting next to her lovingly looking into her face. They were the picture of the perfect American nuclear family. She looked so happy she was glowing. "Good grief", thought Alex, wondering what the husband would do if he found out what his wife had been doing. Hell, those kids were probably the offspring of her anonymous affairs. He was glad that he was on a different flight.

The flight to L.A. Was uneventful. Alex took a cab to his hotel and checked in. It was Friday night, so he had all weekend to himself before meeting with the software company on Monday morning. The hotel suite was superb. It was on the 50th floor and had a spectacular view. There was a sunken living room with a wet bar in the middle of the room. The King-size bed was 3-steps higher than the living room. Both had a sliding door leading to balconies that overlooked a golf course directly below and the ocean only a half-mile away. The bathroom had a Hot Tub/Jacuzzi big enough for 4 adults in half the room. The other half was a giant shower. There were two large overhead shower nozzles and four more nozzles on each of the three walls of the shower. You could easily have a small party in the bathroom.

Tired from the travel, but still wound-up from the unexpected sexual encounter, Alex took a long hot shower, then went down to the restaurant, slipping the panties she'd given him into his pocket on the way out the door. He had dinner and then retired to the lounge for a drink. Sitting in a comfortable chair, drink in hand, Alex stared out the window at the sunset and smiled recalling the day's events. During a second drink a couple sat down on the couch next to his chair. She was about 25 years old, 5' 5" tall and had a nice athletic figure. Her hair was a beautiful natural red color worn loose, hanging down below her shoulders. Her skin was light with a few freckles and she had nice firm smallish breasts, probably a B cup. She was wearing a slinky dark green dress that showed off every curve. When she sat down, her dress rode up her thigh and Alex noticed the garter clips holding up her dark green stockings. Her smile was mesmerizing. Her companion was older, in his early 30's and close to 6' tall. He was most likely Italian with olive skin and chiseled features. Quite the handsome couple.

They introduced themselves as Lori and Adam. They made small talk with Alex and as the drinks flowed they all became more and more friendly. After a few more drinks Lori leaned over and whispered something in Adam's ear. As he smiled she got up and walked towards the Ladies room. Alex watched her walk away from him, admiring her cute ass. Turning back to Adam Alex could tell that Adam saw him looking at his wife. "It's OK," he said, "I don't mind, we both like the attention she gets from other men."

He went on, "You know, Lori has a fantasy that we've both been reluctant to try... until now. What would you say to joining us tonight? She has a fantasy of being with another man while I watch." Alex didn't know what to say. Lori was definitely attractive and he would love to be with her, but what if Adam suddenly got cold feet? Would he get angry? Take his anger out on him or worse, on Lori? Adam saw Alex' apprehension and reassured him saying "Look, come up to our room, we'll take it slow and see what happens."

Lori came back from the Ladies room and Alex saw Adam smile and nod at her. She walked directly to Alex and looked at him with her beautiful green eyes, bent over and whispered in his ear "I hope you like the smell of leather" then took his hand and led him towards the elevators. The three of them got in the elevator and Lori was immediately all over Alex. She was rubbing his chest and nibbling his ear while her other hand was all over his ass. Alex looked nervously at Adam, but Adam was smiling his encouragement. He also had a noticeable bulge in the front of his slacks.

The elevator door opened and Adam peeled Lori off of Alex, pulling her towards their room as she giggled. Alex was feeling better about the whole situation and decided to go along with anything they wanted. She was so damn hot! He couldn't wait to get her clothes off. They entered the room and Lori immediately unzipped and dropped her dress, kicking off her shoes as the dress dropped to the floor. She didn't have on a bra and stood looking at the men wearing her stockings and garter belt, and a tight black leather thong. It was so tight and thin that Alex was reminded of the phrase "camel toe". God she was beautiful. She said "Adam, strip and sit there, Alex, come over to the bed."

As Adam got undressed and sat in the chair facing the bed, Lori sat on the edge of the bed and said, "Alex, I want you to slowly remove your clothes." He stood close to the bed and as Lori lay back on her elbows and watched, he started unbuttoning his shirt. He tried to go slow, but the sight of her there looking at him was a lot to bear. She lifted her stocking-clad leg and rubbed it up and down his legs as his pants came off, then she used her toes to remove his boxers as his growing erection made it difficult for her. Still standing between her legs, she started massaging his balls with her feet. Alex glanced over to the chair and saw that Adam had his dick in his hand and was slowly stroking it. It was impressive, about the same size as Alex' but bigger around. He was circumcised as was Alex. Their eyes met and Adam smiled. Lori said, "Hey, look at me when I play with you" and laughed.

She pulled him onto the bad practically on top of her and they kissed. Her tongue went deep into his mouth and he passionately responded in kind. His hands found her breasts and she squealed lightly when he pinched her nipples. He bent down and took one nipple in his mouth and he suckled lightly as his hand caressed lower, feeling the top of her thigh and the stocking. The feeling of the stocking reminded him of the pantyhose he'd worn and his erection grew. The nipple was hard in his mouth now and he moved to the other breast, licking the underside lightly sending shivers up Lori's back. His hand moved to her pussy and he felt the leather, so tight against her. He tried to put his hand inside but she stopped him saying, "Not yet, you have to earn that first."

Lori moved out from under him and pushed Alex over on his back. She looked her husband in the eye and went straight for Alex' cock. One hand slowly started stroking him as the other fondled his balls, all the time her eyes never left Adam's. Adam was getting noticeably harder as he stroked himself and Alex noticed some pre-cum at the tip of Adam's penis. Adam wiped the pe-cum off with a finger and then licked it off. "You like that baby?" Lori asked, "That turns me on so much!" Alex was turned on as well, he remembered tasting his own cum and wondered if Adam's tasted any different. Lori ran her tongue up and down Alex' cock coaxing a bit of pre-cum from him as well. Still looking at Adam, she licked the pre-cum from Alex' penis. Adam groaned and stroked a little harder while squeezing his balls tightly.

Abruptly she swung her hips around and straddled Alex' face. Bending over, she continued to play with his cock as her ass and leather-covered pussy wiggled over Alex' face. He reached up and put a hand on each of her cheeks squeezing and kneading her beautiful ass. He spread her cheeks and saw the leather thong barely covering her little asshole. She had a few little red hairs poking out and this turned him on immensely. He'd never been with a natural redhead before and he wanted to see her natural bush up close. Pulling her closer her pussy came down on his mouth and he started licking her leather panties. God, it tasted good! The leather smell mixed with her womanly scent was intoxicating! Her juices were flowing, he could taste them at the edges of the panties. She ground her cunt into his face, practically smothering him, but lifting up to give him air periodically. She bent over and he felt her licking his cock, up and down the shaft, taking him in her mouth and slowly sucking. His tongue and lips were trying to get past her panties, but they were too tight. She bent back slightly and he reached his tongue up and licked the leather covering her asshole. The thong there was narrow enough that he could lick the rim of her ass on each side of the thong and he tickled the little hairs there with his tongue. That really turned Lori on and she squirmed and ground her ass into his face harder.

TaraJean
TaraJean
175 Followers
12