Dan had been fascinated with women’s panties since he had found a pair belonging to his sister accidentally mixed in with his clothing. He had rubbed them against his face feeling the silky smoothness. He kept them for a few days until he heard his sister asking about them, then made a pretense of finding them stuck in between the washer and dryer. After that, whenever he had the chance, he would try to sneak in a few strokes against his cheek with a pair of her panties. When his sister threw out a pair that was getting a bit too frayed for her, he rescued them from the trash and hid them in his room. Up to that point, he had only used them on his face, but now he had a pair all of his very own. The next time he masturbated, he used the panties to stroke his member.

The feeling was just amazing and he was hooked. He went to a lingerie store in a mall some distance from his home and bought himself a new pair. When he got home and was alone in his room, he stripped down and slipped into them. The feeling was incredible and he got erect almost immediately. He masturbated himself to a climax using the old pair of panties wrapped around his shaft as he stroked. For awhile, he would just slip them on to get an erection, then use the other pair to masturbate.

One day after he had ejaculated and cleaned himself off, he put the panties back on and found he could wear them without getting fully hard. He started wearing them around the house when he was wearing baggy pants or sweats. As time went by, he learned to enjoy the feel without getting a hard on, so he began wearing them out. Soon he discovered panty hose and started wearing those as well. He was very careful not to wear them when there was any chance he might get caught, like at school, but he would change into them as soon as he got home. He just loved the feel of the soft material rubbing all over his body and often rubbed his chest with one pair of the panties while jacking off with another pair on his member.

By this time, he had purchased a number of items and was very careful to hand wash them or do his own laundry, then kept them carefully hidden in his room. When he went off to college, he pretty much stopped except when he was home for holidays. His first summer home, he bought his first bra and actually wore it out when he was home for Christmas. When he went back to school after semester break early, he went out one night to a bar he had never been to before. As he was sitting at the bar, he spotted a familiar looking girl, but could not quite place her. When he went over to say hi, he got the shock of his life as he finally recognized “her” as a guy he knew from one of his classes. He was about to turn and walk away when the “girl” reached out and stopped him.

“Wait, don’t go. Let me explain first. Please?”

“Ok, but I’m not gay.”

“Hey, I’m not gay either. I just like how I feel when I am dressed like this. And I sure am not alone in that. I see a half dozen others in here that I am certain are men, one or two that I actually know.”

Dan instinctively looked around the room.

“Hey, be cool. Perhaps you should cross this place off your list.”

“Actually, maybe we could talk?”

“Sure. I’m Andy by the way… Andrea when I look like this.”

Dan slowly told Andy his story, telling him how it started and what had happened since then.

“I don’t think I would ever have the nerve to do what you are doing. Wearing women’s clothes in public, and how do you walk in those heels? I would probably fall flat on my face! But the feeling of a pair of satin and lace panties against my co… uhm, skin, is just incredible. And I am not sure that I really want more than that anyway.”

“Well, the heels do take a bit of practice. It’s best to start small with a lower heel first, and work your way up. And as far as the feeling, I agree, it is absolutely fantastic. I started out a lot like you. Then I bought more lingerie, then a nightie. Eventually, I bought a skirt and low cut blouse. I wore those around home when I was by myself. Then I got some makeup and started experimenting with that. Next was a wig. Finally, one night I dressed up and went out to one of the local gay bars. I only hung around awhile, but no one laughed at me or made a big deal about it.”

“But I’m not gay.”

“Well the gay bars also support the transgender and cross dressing communities as well. So I was just another person in the bar. As far as the other stuff, yes, the first few times are hard. You first need to get comfortable in full dress. Have you bought anything other than bras, panties and nylons? And have you shaved your legs yet?”

“So far just those things, and I started shaving my upper legs one day, then chickened out. And I have no idea where to even shop for that stuff. I have no idea what size I would need. The bra was bad enough and it is actually a bit too big, and kinda looks lumpy when I stuff it. I can hardly go into a store and try things on.”

“I suggest first you figure out your size. I would guess you to be about a 38” chest, so maybe around a size 12 or 14 dress or blouse. Maybe a size 10 skirt or jeans.. You can look online and it will tell you how to measure, then will let you know what size it equates to, but that can really vary based on style and even who made it. Your best bet might be to go to a resale shop where you can pick out some stuff, throw it in your basket under a couple of men’s shirts and use their dressing rooms. Plus it won’t cost you an arm and a leg. What size shoe do you wear?”

“An 8 1/2 .”

“That equates to about a women’s size 10 or 10 1/2 . You might also be able to find a wig and some inexpensive costume jewelry. And nobody is going to look at you twice there. Try not to go too over the hill, just something simple. Get used to wearing it inside and walking in the shoes. Once you get comfortable with that, then you can work on going out. And I can recommend a few other places besides here where you can go.”

“Wow, thanks Andy, uhm Andrea. That’s a lot of good advice.”

The two of them sat and talked for a couple of hours and Dan could hardly wait to do more. He took Andy’s advice about checking the sizes online and did a bit of shopping at a Goodwill store about twenty miles from school where he was not likely to run into anyone he knew. He kept all the stuff he bought locked in a suitcase in the back of his closet. Whenever he knew for certain no one would bother him, he locked his door and put on the clothes. After a few months, he was getting pretty comfortable wearing the clothes and walking in heels. He was beginning to feel so different when he was dressed as a woman. Beginning to think he understood how a woman felt when she was all dressed up.

Dan had gone back to the bar and run into Andrea a few more times, and had begun to start wearing more feminine jeans and boots along with the underwear. He had already had longish hair, and he just let it grow, combing it into a more feminine style which took some trial and error. He was also beginning to experiment with makeup, but just felt too uncomfortable with it. Andrea gave him a few tips about the makeup part, suggesting a few sites that discussed it. He also gave him some hints on how to “tuck” his cock so it would not show in tight women’s jeans. When the weather got a bit cooler, and he could wear a jacket, he started wearing his bras out. He had found some inserts which looked quite natural, and stuffing could be added behind that. His biggest issue was getting out of his dorm room dressed up, so he usually brought the stuff in the car and either changed in the car or a gas station restroom.

Finally, the day came when he was ready to go out in full drag. He had checked out one or two of the places Andy had mentioned, but had not frequented any of them, so no one would know him as Dan. Picking a name to use had been a decision he had struggled with. Danielle was the obvious choice, but he wanted to feel different, so he had finally decided on Becca. He dressed up in what he could in his room and did part of his makeup as well. He threw the additional items in a gym bag and slipped out while his roommates were at dinner. As soon as he got a little ways from campus, he pulled into a parking lot, changed his jeans and boots, and put on a more feminine jacket. He did the rest of his makeup, and pulled out the purse he had gotten. He had gotten a new ID made at a place Andy had told him about. They catered to the Transgender and Cross Dressing communities as long as they had a valid ID; they would make them one with the same basic info, just a new pic, name and gender. It wouldn’t get them past a cop, but would pass muster at the bars.

Becca had decided which bar she was going to make her debut at, and headed over there after completing her transformation. She had selected one of the smaller gay clubs where she hopefully would not feel overwhelmed, but would still be able to interact with people. She pulled up in front of the bar and let the valet park her car. She was quite pleased when she saw the valet’s eyes linger on her. And as she walked away, she checked out of the corner of her eye and saw he was still looking in her direction.

She walked into the club and found an empty stool at the bar. A female bartender took her drink order and gave her a smile. Becca took a look around and saw a small dance floor with about a dozen couples dancing. There appeared to be a number of same sex couples dancing, as well as some mixed couples. Looking around further, she could tell that some of the “girls” were actually men. A few were quite easy to distinguish due to their size, or their looks. There were others that she suspected were men, but like herself, were smaller in stature and harder to spot. Some were dressed quite outrageously, which was obviously deliberate.

After a bit, another woman sat down next to her and started up a conversation. Becca had been working on her female voice and was using it quite successfully, or at least she felt like it was. Eventually, after a couple of hours, she had spoken with at least a half dozen men and women and had been hit on by one man, one T-girl and two women. Up close, she was able to see that a few of them were men but she could only tell because she could see the five o’clock shadow, or their Adam’s apple. Some she guessed really were women, but it was hard for her to tell if most of them were just being friendly, or actually hitting on her and if they were, why.

When one of the “ladies” came back for the third time and started rubbing her back, Becca got a little freaked out and excused herself to go the bathroom. Halfway there, she realized she had no idea which room to use, so just left, got her car from the valet and headed back to school. She was almost there before she remembered she needed to remove her make-up and change back into Dan again. She stopped at a mini mart, quickly changed clothes and washed her face. When he walked back out to the car, he was pretty sure the attendant gave him a strange look as he walked past her.

Dan got back to his dorm room and one of his roommates was there studying. He said a quick hello and headed to his room, stuffing all his stuff into the suitcase and locking it securely. He felt confused about the evening, wondering about the people that had tried to pick him up. He was certain some of them had known he was in drag, so were they trying to pick him up as Dan, or as Becca? Were they straight or gay, and what had they thought he was? And just which bathroom was he supposed to use??

Dan decided he needed to talk to Andrea about what had happened. These were things he had not considered until now. While he did love the way he felt when dressed as a woman, he was still very much a male. From a sexual standpoint, he still desired a woman. He had never even considered having sex with a male partner. He felt that dressing as a female on occasion gave him a bit more insight into women. Especially after getting hit on, he now understood, or thought he did, how women felt about that.

Over the next few days, Dan kept going over how he felt about what had happened at the bar. And not just how he felt about the people that had tried hitting on him, but also how he had felt about them. He really had only been thinking about their reactions to him at first. But the more he thought about it, he realized that he had been quite flattered by the attention and even a little aroused. And the arousal was not just from the women.

He finally ran into Andy in class and said he needed to talk to him. They made arrangements to meet at a bar near the campus later that afternoon that should be pretty quiet then. The rest of the day seemed to drag by until it was finally time to go. Andy was already there when Dan arrived and had found a table where they would be able to talk.

“So, tell me all about your big night out. How did it go?”

“Well, logistically it was a success, I guess. I looked pretty good, I think, and sounded ok. I stayed a couple of hours and chatted with a number of people; even getting hit on by a couple of them.”

“Okay, how was it not a success? Who hit on you and how did that make you feel? Obviously something unexpected happened.”

“One guy, I think he was straight, though I’m not really sure, got pretty aggressive with me. He bought me a drink and after that, it was like he expected a lot more from me. He tried to monopolize my time, until a couple of girls came over and basically told him to get lost. I sort of saw myself a bit in that, and now have some idea how women must feel when guys do that. We can be an inconsiderate bunch, can’t we?”

“Yea, I think we have all done something like that at one time or another. What else?”

“One of the girls that came over turned out to be a cross dresser or a T-girl. I’m not sure which. But he, or she rather, knew I was a guy right away. We talked for a bit and she seemed really nice, but later she came back and started getting very touchy feely. I got a little freaked out, because I knew she was a guy, and she knew I was a guy. I excused myself and headed for the bathroom, until I realized I had no idea which one to use. So I just left and went back to the dorm. I almost forgot I was still dressed as a girl and had to stop at a mini-mart to change.”

“But before that, two girls, pretty sure they were a lesbian couple judging by the way they were kissing and looking at each other, came over and tried to pick me up. They made no secret they wanted me to join them for sex. I got pretty flustered and finally spit out that I was a guy. They said they knew that.”

“Wow, quite an experience for a first outing. So how did you feel about everything that happened?”

“I got really confused; partly because a guy dressed as a girl tried to pick up another guy dressed as a girl. Did he think I was gay? Was he gay? Did he feel like a woman picking up a guy for sex? And the two lesbian girls… or bisexual girls, or whatever they were. What were they thinking?”

“Those are all very good questions. But more importantly, how did you feel? Did any of it excite you at all?”

Dan blushed deeply.

“Actually, I was quite flattered by the attention and yes, I was aroused.”

“By the men or the women?”

“Well, by the women, of course; especially after they said they knew I was a guy. I mean, what guy doesn’t fantasize of having sex with two lesbians? But maybe even more so, because I could never see that happening if I had been there as myself. However, I was also getting aroused by the T-girl, and that really confused me. Which, I suppose is why I got so flustered when she started whispering things to me. And then when I headed for the bathrooms, I got even more confused. Just where do you go?”

“I personally use the ladies room when I am Andrea. It does take a bit of getting used to, but you will. As far as the other stuff, that is all pretty normal. And at some point, you may actually want to have sex with someone. You just need to figure out who and why. Just remember, I believe we are all bi to some extent and sexual experiences that are different than what we are used to don’t make them, or us, bad. Some are just that… a different experience, but others can be quite liberating. We are sexual beings and we should allow ourselves to be open to that idea.”

“One thing I did not really expect was that a female friend of mine came over the night after I had been out. She and I occasionally hook up, which we did that night. And it was some of the hottest sex we have ever had. She even asked me what had gotten into me. I blurted out something stupid about watching some porn and being really horny, but I doubt she bought it.”

All Andy did was laugh. They finished their drinks and headed back to campus.

As Dan went out more, he was getting increasingly comfortable in the Becca persona. She started hanging out at a few places on a regular basis and began making friends with some of the other regulars. One day, one of the trans girls she had seen watching her approached Becca and said she want to suck her dick. At first, Becca hesitated, then finally followed Candi out to her car towards the back of the lot. Candi opened the door and sat down on the edge of the seat, pulling Becca towards her.

She undid Becca’s jeans and pulled them and her panties down, revealing her penis which was already becoming aroused. Candi took Becca’s balls in her hands and expertly massaged them. At the same time, she began sucking on her penis. Becca closed her eyes and leaned her head back, letting out soft moans. Pretty soon, she put her hands on Candi’s head and guiding her pace. She never imagined how good a man’s mouth would feel on her cock, and how different it would feel from blowjobs she had gotten from girls in the past.

This went on for quite some time, Candi knowing just what to do to bring her to the edge and hold her there, then slowly relax, just to do it all over again. Becca was so focused on the feeling in her cock, she barely felt it when Candi began rimming her hole and working a finger in. But as the finger began to fuck her ass, then press against her gland, she exploded into Candi’s mouth. She grabbed her head and pushed her cock in as deep as she could as Candi licked and sucked and swallowed every drop.

As Becca finally relaxed her grip on Candi’s head, she continued to lick and suck on Becca’s cock and finger fuck her ass. At some point, she worked a second finger inside. Becca could barely believe it when she started getting hard again. Candi looked up at her and smiled.

“I have another place where you can put that sweet cock of yours, honey.”

Before she knew it, Candi stood up and lifter her skirt up to her waist. She pulled her panties downs and leaned into the car resting her hands on the seat with her arms extended. She wiggled her ass at Becca, who had been stroking her member, getting it hard again. She rubbed it up and down, finally pressing it against Candi’s manhole, then pushing in slowly. Once fully inside, Becca began fucking her enthusiastically; cumming quite unexpectedly after about five minutes. She began to apologize, but Candi just turned around and kissed her

“First time inside a man hole, hun?”

“Yes.”

“Well, you did just fine, sweetie.”

It was only then that Becca noticed Candi’s hand was holding her own cock and was covered with cum. Candi pulled some tissues from a box in the car and handed them to Becca, then pulled several more for herself. They both cleaned themselves off and straightened their clothing. Candi headed back into the bar, but Becca felt a little embarrassed, figuring everyone would know what they had been doing, so she excused herself and headed back to the dorm.

On the way back to the dorm, Dan changed and found himself thinking about what had just happened. A few months ago, he would never have even considered doing something like what had just done. He was a little amazed at how easy he actually had found it to do. Over the remainder of the school year, Becca became more and more comfortable, even to the point of trying a few skirts on in the privacy of her room. But even though Dan was not overly hairy, and had fair hair, he was reluctant to shave his legs with summer approaching.

And once back home for the summer, Dan was not sure just what he was going to do. There were a few gay bars close to where he lived, but he felt they were maybe just a bit too close for comfort. He would have to check out some of those in the city, though he would probably go in first as Dan to see if there was a cross dressing or transvestite presence there before he went in as Becca. The one thing Dan knew for sure was that he was loving this new side of himself, and that he would continue exploring it, whatever that meant, and where ever it took him.