First Time Is A Great Time!!

The day was going just as any other day. A long day at work followed by the short drive home from the office. Jeff walked in the door at the usual time and took the usual shower. A hot 15-minute shower spent washing off the feeling of a full day's work. He stepped out of the shower and wrapped up with a towel. A sense of excitement came over him. He had been waiting for this all day long. A new black dress had arrived in the mail yesterday along with a pair of black platform sandals. It was the perfect little summer outfit for a night on the town. Unfortunately, this outfit would never see a night on the town.

In recent years Jeff had become more comfortable with dressing up. He had come a long way from the humble beginnings. As a young boy he didn't understand the desires he had felt. The desire within always scared him. Growing up in a home with two rough brothers and a sports loving father. He did not want to be different from them so he took interests in all of the things that they did. However, there was always something that drew him towards his mother's closet.

Many days when he was home alone, he pulled out her shoes and would slide his feet in. He enjoyed walking past the mirror looking at his legs in the shoes. One day at the age of 16, he got up the nerves to look into her underwear drawer. It was something that he knew he should not be doing but he could not help himself.

Pulling out a pair of thigh stockings like the ones he had only seen on TV, he immediately pulled them on. He was taken over by the feeling of them against his skin. It was a feeling that he would never forget. And whenever he had the chance, he would sneak into the drawer and pull out the stockings, carefully pulling them on to avoid any runs. This gradually escalated to pairs of underwear that he would sneak during the day to sleep in at night. He always thought he would be caught but never was found out. Then again maybe it was discovered and his mother didn't have it in her to confront him about it.

Now as an adult, he still didn't completely trust his feelings. He never considered himself to be gay as he had never been completely attracted to men, only transsexuals and crossdressers like himself. These days, however, he was starting to embrace the fact that he was actually bisexual even though he had never completely been with a man. This was something that he had thought about doing before but could never get up the nerves to actually do it.

Jeff had struggled for a long time wondering what people would think of his choices. So for Jeff, days like this at home became the best times of his life. He always felt so free and liberated at home when dressed up. He wasn't sure if he would ever know what that made him, but he was sure that it made him happy.

Leaving the bathroom, he went into the kitchen and poured himself a tall drink. After taking a few sips from the glass, he turned and headed for the bedroom and made his way to the closet. After pulling the dress and shoes out of the closet, he turned on some music and walked back into the bathroom to apply a little makeup. He wanted to go all out for his first time in the new outfit.

After finishing his makeup he returned to the bedroom and put on the full outfit. First sliding the thigh high stockings on one at a time. Then slipping the dress on carefully so as not to stretch the new material. The dress fit perfectly, clinging to his frame in all the ways that he imagined. He could feel the tight dress wrapping around his slim waist and clinging to his petite little ass. It was for the feeling of dresses and outfits like this that kept him working out 5 days a week. At 5'7" and 130 lbs, Jeff worked hard to keep the curves exactly where they needed to be.

Jeff studied his closet. Finally finding the perfect pair of shoes. A classic pair of black stiletto pumps. Simple yet, sexy!! Looking at himself in the mirror, he started to get turned on looking at the dress accentuating his hips and ass. Lastly, he pulled out the wig with the shoulder length jet-black hair. The look was now complete!

Satisfied with everything, he walked out the bathroom and almost dropped dead. As he stepped out into the hallway, the maintenance man, Ty, greeted him. Jeff had completely forgotten that he had placed an order for service in his apartment. The music must have drowned out the knocking on the door. If he had heard, he would have told them to come back a different day. That was the last thing on his mind now, as he stood in front of the maintenance man in a sexy pair of heels and sexy black mini-dress.

Jeff stood speechless in the hallway. There were no words to find. Finally Ty broke the silence. "I'm sorry, I knocked"

Jeff replied, "Are you sure, cause I would not have allowed you to enter." At this point, he was not able to hide his embarrassment. No one had ever seen him like this.

"I can come back later," stated Ty the maintenance man as he turned to leave. Realizing that at this point it didn't matter if he left or stayed at this point Jeff told the maintenance man to hurry up and finish what he came to do. Jeff walked into his bedroom and closed his door behind him. He was obviously embarrassed and flustered.

30 minutes later there was a knock at the bedroom door. Ty opened the door to say that he was finished and was about to leave. Jeff didn't make eye contact as he acknowledged him. "Can I ask you a question?" asked Ty.

Jeff finally looked up at him. "Why do you do this?" was the question.

Jeff said, "I always have. I honestly can't explain the feelings that I get when I'm dressed like this. It turns me on so much that I can barely control myself." Jeff started to realize that he was slowly beginning to feel more comfortable talking to Ty. He really appreciated the fact that he didn't make him feel bad about the situation.

Strangely Jeff appreciated this moment. It had always been his dream to go out dressed up but never had the nerve to. He had his doubts on how passable he would be in public. This encounter served as a perfect "first-time" for him. Suddenly, a strange thought popped into Jeff's head. Another one of his fantasies was to service a man while he was dressed up. Not knowing if he would get this opportunity again he decided he would give it a chance. Jeff figured if he could turn this man on, then passing in the outside would be easy.

Jeff stood up to and started towards the door. "Can you show me the work that was done?" asked Jeff asked he walked down the hall. Hundreds of times he had practiced his walk, trying to perfect the sway of his hips. He knew exactly what it was that guys like to see.

Walking down the hall he could feel the material of the dress swaying with the movement of his hips. He could feel Ty's eyes following his ass as he strolled down the hallway towards the laundry room. Ty followed to point out the leak that he found and show the completed work. Jeff took this opportunity to take a closer look. He leaned over to look at the back of the washer. He could feel the back of his dress lift up to reveal the lace top of his thigh high stockings. "I have to say, it does look good Ty. Don't you agree?" asked Jeff.

"Y-Yes" stammered Ty. "It's good work. It should hold up and if not, you know where to find me." It was at that instant that Jeff knew that he had the attention that he wanted from Ty. Jeff went to walk towards the living room. He made sure to make contact with Ty just enough as he walked past.

"Ty" called Jeff, "have you ever been with a man?" All the while, Jeff was focusing on being as sexy as he could while walking away. Keeping his hips swaying from left to right with each step. The whole time, hoping that he didn't trip over his 5-inch stiletto heels.

Ty now was completely taken aback despite his obvious growing erection. "No!" he replied emphatically. "I'm not gay!" Ty quickly shifted his attention to his tools scattered about.

Jeff smiled slyly. "I didn't ask if you were gay. And by the way, there would be nothing wrong with that. But aren't you in the very least intrigued by what you're seeing right now?" asked Jeff. "I mean, this is my best attempt at being sexy and being what guys would want. How do you think I am doing?"

Ty didn't know how to respond. Clearly he had been turned on by Jeff but didn't want at all to accept it. "If I were to be completely honest, and it doesn't mean anything, I have to say that you have done a good job transforming. I'm sure that someone who is into this sort of thing would be very pleased."

"This sort of thing?" said Jeff with a perplexed look. "Well what is your thing Ty?"

Ty was quick to respond, "Something with no penis involved!" Jeff was all in now. He made it to the couch with no mistakes and no fall. Sitting down ever so gently; he stuck out his left leg in the air and crossed it over his right leg.

"So Ty...do you like legs?" Jeff shifted just enough to flash the top of the thigh highs again.

"I do," he answered. It seemed that Ty had a pretty big bulge in his pants. Jeff couldn't take his eyes off it. He wondered what he would do if he could just touch it.

"And what about a nice, slim, sexy frame? Don't you like seeing that?" was the next question.

"Of course" answered Ty. Jeff stood up after hearing his answer.

"But I have both of those things Ty. What's wrong with me?" asked Jeff as he started walking towards Ty.

"You have a penis!!" shouted Ty as Jeff walked closer.

"Oh yeah. I do don't I?" said Jeff, pausing in front of Ty. Jeff placed the tip of his finger in his mouth as if in deep thought.

"But what you see in front of you seems to be turning you on. But in your mind, you feel there is something wrong with it because of some pre-conceived notions or standards set by society. Why does society have to determine what gets you excited? Why does society have to determine was makes you hard? Why does society have to determine what you can or can't enjoy?"

Jeff took his hand and put it on Ty's crotch. It was just as he knew. Ty was hard!! Feeling his hard cock took Jeff to new heights. He had never touched someone else's before. It was so hard! It was so exhilarating knowing that he had made that happen. Ty couldn't hide his excitement any longer. Jeff looked Ty in his eyes as he began to rub his hand up and down his shaft.

"Don't you like this?" asked Jeff. Ty didn't answer. "It's ok. I haven't done before either," stated Jeff. Ty still didn't answer. He looked away as Jeff pressed in closer.

Jeff was fully engaged now, his own cock pressing against the thong under his dress. His senses were at such a high level right now. The stockings against his legs felt like a steady breeze on a hot day. The feeling of the strings of his thong made his cock start to throb.

This was it! This was a moment that Jeff had only fantasized about plenty of times. He had no idea how to handle it, but that wasn't going to give me pause about trying.

Jeff unhooked Ty's pants. Ty didn't stop him...so Jeff unzipped and slipped his hand in his pants. He took a handful of Ty and pulled it out. For the first time in his life, Jeff was looking and holding a cock that wasn't his and was not on a computer screen.

Ty's cock was amazing. Thick, long, throbbing. He couldn't hide it anymore that he had been turned on by Jeff. Ty stared at Jeff and didn't say a word. Jeff slid down to his knees. He rubbed his hands up and down Ty's legs as he playfully slid his tongue around Ty's penis. This was unfamiliar territory for Jeff but he was more than ready for his first experience. He already had countless numbers of fantasies in his head of what he would do in this situation.

Jeff slowly took Ty into his mouth. He was careful to remind himself to be sure to take it easy and avoid biting down. Slowly Jeff worked his mouth back and forth on Ty. Jeff was excited with how much of Ty he was able to take inside of his mouth. Jeff closed his eyes and concentrated on his back and forth movements on Ty. He tried to be as rhythmic as possible. Jeff switched back and forth from using just his mouth to including his hands to increase the sensation of the blowjob.

After a while, Jeff looked up to Ty. "Is this the sort of thing that turns you on?" he asked.

"Just keep sucking," replied Ty.

Jeff was more than happy to oblige. He was so excited that the first cock he put into his mouth was so huge. His cock was so hard asking to come out. Jeff pulled his cock out and started to stroke it with his free hand. It didn't take long before Jeff was coming while still on his knees.

Jeff kept at Ty, wondering if it was that he wasn't good at this blow job or if it was just Ty's stamina that was making him hold out from coming. Jeff decided to work his mouth faster on Ty's cock. Rocking his head back and forth and working his hand at the same time. Jeff ran his hand over Ty's balls. He caressed them then ran his tongue over them. Jeff could hear the moaning of Ty pick up. He started thinking that he may be close to coming.

Suddenly, Jeff could feel a shift in Ty. He started to feel a buckle in Ty's legs. Jeff knew that he had gotten Ty to that point. Jeff was so excited and turned on knowing what he was doing. Jeff increased his mouth and hand motions. "I'm going to come," exclaimed Ty.

Jeff buried his face onto Ty's cock. Seconds later, Jeff felt Ty's warm release shooting into his mouth. Jeff had imagined this so many times. He savored the taste as loads shot repeatedly into his mouth. He took it all and swallowed it happily.

Realizing what just happened Ty hurriedly pulled up his pants. Ty grabbed his things and headed for the door. Jeff stood up and turned towards Ty. "What happens when more service is needed?" asked Jeff.

"I'll call you," replied Ty. "You certainly serviced my needs!"

With that said, Ty turned and walked out the door. Jeff could not believe that what had started as an embarrassment had turned out to be such an experience. He was proud of himself! After that encounter, he knew that he could go out and not worry about what anyone thought of him. But this would not be the last encounter between Jeff and Ty...

To be continued...