Lexi and Dylan

Lexi sat in the back of the cab, biting her lip. A small smile was draped across her face and a masculine musk across her lips, from her previous location. She could still taste him on her tongue. Of course, he didn't taste her. That's not what it was about. Lexi was transgender and just finished meeting up with a guy from Craigslist. It was 2005 and she was 21 years old. Lexi had been Lexi for almost as far back as she could remember. At a very young age, she would prance around the house, telling her parents she was a girl. Her parents, wasps from the east coast, couldn't think about having a gay son in the late eighties and early nineties, so they raised Lexi as Lexi, and started her on hormones as soon as the age was appropriate. She went through all of school without anyone ever knowing she was born a boy. She even joined the cheer squad in high school and just casually avoided any fully nude events, such as showering and the occasional party that erupted into skinny dipping.

Because of her early exposure to estrogen, Lexi, especially at twenty one, did not look like a typical transgender woman. There were no mistaken jawlines, or questionable bone or muscle structures. Lexi looked like a beautiful brunette Paris Hilton, which at the time, was a good thing. She lived in Los Angeles in a small house her father paid the rent for. She was within walking distance to a lot, but going shopping, meeting friends, and going out were all issues because she didn't have a car. Because of her parents' wealth, however, she never had trouble getting around or finding the best fitting high fashion outfits. Her outfits were always either gypsy dresses, or similar flowing tops with factory-ripped Michael Kors jeans. Lexi's sunglasses were always large and always on.

Often times, Lexi would joke that she still kept the male sex drive. Living in Los Angeles at the height of Craigslist popularity, this was not a hard beast to feed. Sometimes, if she wanted to go somewhere, like the Beverly Center, to meet some friends, she would knock out two birds with one stone. She'd try to hook up with a guy, but make him pick her up and drop her off, wherever she wanted. While oral sex was nothing uncommon, Lexi had only ever slept with two guys. She saved that part of her for someone she felt comfortable with and adored by. She felt she deserved that and in truth, she did.

This particular day, her sitting in a cab, was a bit different. Lexi woke up and spent the day thinking about going down on a guy. It was a thought she woke up with and couldn't shake. She surfed the casual encounters section of Craigslist looking at posts. Men were simple folk and typically only posted some picture of their dick, expecting some woman to see it and say to herself "I have got to have this thing!" It never went that way, but the men always persisted in their attempts. Going through ad after ad, she finally found a cute guy who posted an ad in the men seeking women section. His pictures were just his face and his upper body and he wanted to 'make out and get some head'.

Lexi laughed at the thought of it. Wouldn't it have just been easier to say 'I want head', she thought. She liked his pictures and decided to respond to him. This was always a risky move and she accepted the risk. Being transgender is not something to be ashamed of, but it's something that some ignorant people can go nuts over. Anytime reciprocation was on the table, Lexi would never reply to a men seeking women ad. There were three encounters that she had been outed as transgender that had went very badly, so she was cautious about it ever since.

The first time, when she was back on the east coast, she was making out with her boyfriend. They were only 18 and had been dating for about a week. The guy got a little too excited and dove right between her legs, trying to finger her through her underwear. When he gripped her crotch, he freaked out and jumped up out of the bed. He began calling her terrible names and yelling. In a spur of the moment defense, Lexi grabbed his dick through his jeans and threatened to tell the whole school he was gay if he ever said a word. The boy shut his mouth and agreed. He left scared and embarrassed, and Lexi spent the rest of the day sobbing in her bed.

The other two times were both hookups in Los Angeles that went a little too far. One guy freaked out and yelled at her to get out, and the other tried to go along with it, but ended up almost vomiting right on her stomach. Lexi knew that she was lucky in some of those cases. She'd watched films like Boys Don't Cry and assumed the worst sometimes. She feared being discovered by the wrong person and physically abused, just for being who she was. This all led to a long history of chatting and instant messaging to vet someone's personality. The best anyone had at social media at that point was Myspace, which didn't tell you much about a person.

By lunch time, she had been talking to 'make out and head' guy for a couple hours online. At this point, she'd sent face pictures of herself and she'd seen all of him. He didn't live too far, so she spent the cab fare to go meet up with him. He ended up really actually enjoying the making out, kissing her for almost ten minutes straight, before she unzipped his jeans. He tried to touch her, but she kept pushing his hand back down her thigh. When they finished, she hailed a cab and was on her way back home, still biting her lip and still smelling of him.

North of Lexi's Los Angeles rental, in the Valley, Dylan was also searching for a hook up of a different kind. Dylan had always considered himself to be straight, but had no qualms about discreetly exploring things that made him curious. Dylan was twenty two and had just been left by his long-time girlfriend, Angie. Dylan and Angie moved out to Los Angeles together a year earlier from the dull drab of the Midwest. Angie had family in Los Angeles and Dylan had nothing going for him, so the two made their way across the country in Angie's car, without much more than clothing and some Ikea furniture.

Their relationship had been doomed from the start. Dylan was hanging out with Angie and her friend, Cera. Dylan like Cera a lot, but through countless drunken close counters, she continued to reject him. One night, during an alcohol-induced massage, Dylan made a pass at Angie and she reciprocated. The two began hooking up and were dating, then living with each other all within six months. The timeline moved too quickly, but they both did it anyway. Dylan and Angie broke up and got back together three times before deciding to move to Los Angeles together. The proof was in the pudding.

After moving to Los Angeles, Dylan found all of his work on Craigslist. He did everything from cleaning houses to renovating houses. Anything he could do to make a dollar. All of the time spent on craigslist began to prove fatal to their Angie and his relationship, as he kept finding himself browsing through the personals section. Depending on whether or not he was drinking, Dylan would sometimes respond to ads. He never did it to follow through and meet up with anyone, but more as a sexual tease to see what kind of email exchange and pictures he could get from the other person.

After multiple breakups and a complete lack of trust, partially created by her own cheating, Angie began snooping into Dylan's emails. It was hurtful at first, but she began to feel sick when she came across one particular replay Dylan had written to a transgender woman. He described in vivid detail what he wanted to do to every part of her body. Angie read the email and it filled her with rage and fear. Her previous long-term relationship ended with her then-boyfriend coming out of the closet and she feared it was happening again. Upon confronting Dylan, he tried to explain his curiosities to her, but to no avail. In her eyes, and the eyes of many others, this was cheating.

Dylan's Craigslist obsession eventually ended their relationship and Angie moved back home. After she left, Dylan's friend got him a job doing production work on television shows and he found himself living on his own in a cheap studio apartment. He dove deep into the bar scene and into the Craigslist personals. Dylan would hook up with women from local bars and chat with men from Craigslist. At first, he didn't meet up with anyone off of Craigslist and still used it almost as his form of pornography. He'd chat, trade pictures, sometimes phone calls, get off and move on.

One particular afternoon, after paying rent, but having next to nothing left over, he decided to exploit himself. Dylan posted an ad to let someone watch him shower for fifty bucks. He'd broadcast himself showering and masturbating on a webcam before, so he thought he could maybe make some money doing it in person. Within minutes of posting the ad, Dylan's mailbox was filled with replies. After checking a couple of pictures, he replied to one ad and made arrangements for a guy to come over.

The whole event went by very fast. Tall, handsome thirty-something blonde comes in, Dylan strips and showers while masturbating and taking directions from tall blonde, they both climax, blonde pays Dylan, blonde leaves. After the tall, handsome guy left, Dylan shouted to himself in his apartment: "that was fucking hot!" He had ended up surprising himself. Being directed and the being the object of someone's temporary relief of lust was the turn-on he didn't realize he had.

Even though the first time was because he was broke, Dylan kept having men over to watch him, regardless of his financial situation. Some guys just wanted to go down on Dylan, which he had no issues with. His paranoia of cops occasionally made him get verbal agreements from guys, making sure they understood that they were just paying to watch him and anything else that happened was just something else that happened. The men always agreed, and Dylan ended up totaling four or five encounters this way.

His weekends would sometimes consist of showering for another guy, then using that money at the bar later, where he would meet and hook up with a girl. Dylan's sex life was encompassing a large amount of his time, and at 22 years old, he had no issues with it.

This particular afternoon, the same in which Lexi was just getting home from her Craigslist meet up, Dylan was just going through replies to his ads. Nothing seemed appealing and he wasn't interested in any of the guys he was talking to. He rarely even looked at the women seeking men section, as most of the women were either computer bots or guys pretending to be women. His knowledge of this was vast, as he posted there sometimes, too. After browsing through personals, Dylan clicked over to the t4m link.

While always much lighter in the amount of postings, Dylan loved clicking through the transgender section of Craigslist. He would often fantasize about being with a transgender woman. In his mind it was the best of both worlds. As if he had combined one night of hook ups with a guy at home, then a girl at the bar, into one person. A beautiful soft woman with something extra, something different, something special.

This particular afternoon, he spotted an ad that caught his eye. In the transgender section, often littered with married crossdressers, Dylan came across a picture of a beautiful young woman. Her body and face and fashion were completely female, with no hidden backstory of a different gender at birth. She was almost celebrity-like in her fashion-sense and the way she seemed to carry herself in the few pictures she posted. Believing it was probably fake, Dylan responded with a snarky, sarcastic tone, and included a picture of himself. He laughed at himself, hiding the disappointment that this was probably another computer bot trolling Craigslist. Dylan sent his email, built a fantasy in his head, and brought himself to climax, before going to sleep.

On Sunday, the next morning, Lexi got out of bed and began her morning routine of coffee and checking emails. As she scrolled through the junk mail that accompanied her AOL membership, she came across a reply to one of Craigslist ads she almost forgot she posted. The reply was cheeky and sarcastic, but in a funny way and put a smile on her face. Lexi's smile widened when she opened the picture to see a tall, handsome man with dark hair and broad shoulders. His eyes caught the light perfectly and made her stare at his face. Lexi scrolled up and down the email reading it over again and opening his picture in a separate window to keep on screen. Upon noticing that the sender, Dylan, also had an AOL account, she immediately went to her instant messenger and typed in his screenname.

Dylan, about the same time was checking his email and reading the latest George W. Bush blunder scrawled across his AOL homepage. As a ding went off and loudly vibrated the small speakers of his thick laptop, he looked over to see an instant message. The message was from someone named PinkLuxx.

PinkLuxx: You're pretty hot.

DylanBanks83: Who is this?

PinkLuxx: Lexi. You responded to my ad.

DylanBanks83: Oh! Hi. Haha

Dylan immediately began shuffling through his sent folder in his email. He had responded to so many ads, he couldn't figure out immediately who it was to. As he opened the response and found her screenname, his skepticism returned from his initial reply.

DylanBanks83: So is that picture actually you?

PinkLuxx: Yeah, why?

DylanBanks83: You're just very beautiful and so I'm a little skeptical. 

Lexi was already a little annoyed. She knew the whole game of Craigslist and verifying who you are, but he responded to her. She didn't understand why she had to verify anything to him. It should be the other way around. In an effort to appease Dylan, she sent a link to her Myspace page and requested on in return. Dylan complied and the two explored the photo galleries and wall posts of each other's early social network sites.

As Dylan clicked through Lexi's pictures, he couldn't believe it. Photo after photo was this beautiful young woman. She was gorgeous in every picture, her beautiful green eyes usually covered with sunglasses, but always able to tell a story. Dylan was building a crush immediately, or at least an infatuation.

Lexi began doing the same thing, scrolling through comments and pictures. Dylan was cute. He had the persona and look of any other straight guy. His photos were either just him or him with women. His build was confirmed through many photos as slim, but broad in all of the right places. His 6'3" frame was proportioned perfectly, easily displayed in the tee shirts he wore that were almost too small. Lexi went back to smiling instead of being annoyed and they continued chatting online throughout the morning.

It wasn't long before they arranged to meet up. The plan was for Dylan to come and pick up Lexi from her place and go back to Dylan's apartment to fool around. Dylan walked around his apartment, nearly erect the entire time, getting ready to leave. He cleaned himself up and tried to make his place more presentable. Living on his own and not having to impress anyone had taken its toll on the cleanliness of his apartment. The only thing overshadowing his excitement were his nerves. He had never done anything with a transgender woman before and was still skeptical in the back of his mind that it was the woman in the photographs.

Lexi, excited with anticipation, also found herself tearing around her small house, looking for the right outfit to wear. She settled on a loose, flowing shirt, but was between choices on her jeans when her phone rang. She answered to hear Dylan's voice for the first time. He was outside waiting for her. Lexi went over to the second story window and looked out at him. She was relieved and excited to see it was definitely the same guy from the pictures she'd seen. Leaning out the window a bit, but not enough to show she didn't have pants on yet, she yelled down to him, slightly flustered.

"I'll be right down!" her voice caught Dylan's attention as he looked up to see her. Even from the height and distance, he could see those beautiful eyes and smile. When she came outside, Dylan was already back in his car. As much as he was trying not to worry about it, he couldn't help but be self-conscious and worry about someone seeing him with a transgender woman. The thought made him mad at himself and he spent the time waiting in the car mentally beating himself up for it. His mental abuse stopped abruptly when Lexi opened the passenger door.

"You're not going to get the door for me?" she joked, hopping in the air conditioned car. Dylan responded with an awkward laugh as she buckled up and they began driving. Lexi couldn't help herself and kept staring at Dylan.

"What?" he asked.

"You're just really hot!" Lexi replied, laughing and smiling. Her confidence was almost overpowering to Dylan, who was not yet comfortable with the situation. The laughter and straight forward comment began to loosen him up, though. In a decision to calm the nerves, Dylan made a decision to stop Trader Joe's for some wine. He asked Lexi before stopping and she was fine with the situation.

Walking through the grocery store, Lexi walked in front of Dylan. Her tight jeans were ripped just below her ass, revealing the tan-toned skin of her thigh. Lexi's small 5'2" frame bounced around the store and Dylan instinctively began guiding her and walking next to her, until they reached the wine display. In a save from a possible awkward moment, Dylan quickly pulled his hand back as he went to hold hers on the way to the register. The connection was eerily immediate and he was happy to be out with her. In fact, as he paid for the wine, he realized she was hot. He was out with a hot girl in public. This quickly relinquished any remaining uneasiness Dylan felt about the situation and a few reciprocated smiles were shared in the store before they made it back to the car.

The rest of the drive to Dylan's apartment was filled with small talk. Subjects varied, but the level of comfortability remained constant. Lexi sunk into her seat in the front of Dylan's used Corolla in a way that showed she was more relaxed than the cloth seats typically allowed. Dylan stopped resisting his urges and told himself it was fine, as he reached over the shifter and placed his hand on Lexi's, continuing to talk. Her fingers played with his and neither one acknowledged what was happening between their hands while they drove down the road.

At Dylan's apartment, he turned his key into the door, hoping Lexi wouldn't be grossed out or put off by his place. Lexi stepped inside and began taking the whole place in. Little decorations and movie choices made her begin to see an even more rounded picture of who Dylan was. It became quickly obvious that in the short time they had already spent together, she liked him. This little hookup became even more exciting as that feeling was shared as Dylan came back from the kitchen with two glasses and an open bottle of wine.

"This is fine, right?" he asked, jokingly. "Drinking wine at one in the afternoon is normal, right?" Lexi chuckled at his question, staring at him, fighting off anticipation.

"No judgement here!" she responded, "but I'm all set on that, thanks." Dylan looked down a moment, slightly embarrassed. He set one glass down and began pouring wine in another. As he gulped down a few swigs, it was clear to Lexi that he was nervous about what might happen. His obvious attraction to her started to make her concerned that maybe he didn't know she was transgender. This thought concerned her and she didn't want to waste any more time.