A New Adventure... Ch. 04

This is the fourth installment of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real.

After my last encounter with Mia things really started to cool down on the TS/CD front for me; I'd met a couple of girls who really interested me and were satisfying my sexual needs. My interest in sneaking around and having some good old anonymous sex was winding down and I was no longer really feeling that "forbidden" taboo feeling / adrenaline rush I'd gotten previously.

It took probably a month and a half, maybe even two months before I seeked out my next CD experience; while I had met some interesting girls I was still keeping my options and my eyes open. One night whilst scrolling the ol' dating apps, an extremely attractive girl caught my eye; it just so happened she turned out to be a cross dresser. It was late but we quickly set something up (it was probably already 3 AM) but we both knew what we wanted.

After a short chat, a dick pic, and some negotiating (IE: can you deep throat?) we decided to meet up; she lived in Orange County which actually wasn't TOO far from where I lived in LA. The drive was probably around 35 - 40 minutes; I'd grown very tired of making long commutes to hook up with these random CD's and TS so normally I would not have made the drive but this one was hot.

Unfortunately she told me she lived with her parents and that she wouldn't be able to dress up for me; she also would not be able to host and neither could I (I had a roommate at the time who wasn't aware of any of this). I was horny and really wanted to bust a good nut so I decided fuck it, we'll just do some car stuff (which again, I normally hate and would not go for).

I texted her periodically on the way to her place to make sure she didn't "fall asleep." There's nothing worse than driving 40 minutes for someone to flake and then you've gotta go home empty handed.. And then masturbate. She was very eager to suck my cock and made it very clear so I had no doubt she would be ready when I got there.

"I'm here." I texted her.

"Park a little down from my house." She instructed.

I threw my car in reverse and headed back down the street a bit; it took several minutes before she came out of the house and during the wait I started to get the adrenaline rush that I usually do in these situations. When she finally came around the corner she was wearing a large hoodie with the hood over her head and a pair of shorts; I never even saw her face.

She gets in and directs me around the block to a dead end street; it's about 4 AM and there's not a car or person in sight.

"I've gotta piss." I told her after the lengthy commute; the nerves always get to me before these meetings.

I hop back in the car and lower my shorts to the floor; I lean my seat all the way back and throw a hand behind my head, completely relaxed. It didn't take long before she was leaned over in the passenger seat across the console of my car with my cock completely down her throat. I've said it over and over again throughout this diary and that's just because each time was better than the last but this was some of the best head I've ever received.

"Slow down." I exhaled very quickly.

It didn't take long before I could feel the overwhelming sensation of an orgasm building at the tip of my cock; I drove all this way, I wanted to enjoy this. She turned her attention to my balls and then to my body; she pulled my shirt up over my chest and kissed her way up to my nipples. She twirled her tongue around and around and sucked on my nipples; personally I'm not a fan of my nipples being played with so I pushed her head back down rather quickly.

She went back down to my cock and continued to aggressively suck it; using her hand to twist and turn up the shaft directly behind her mouth making a sort of vacuum. I could feel my orgasm coming along yet again so I pulled her head back and she continued to stroke the shaft; she was relentless. I decided to reach over her back across the car and shove my hand down the back of her shorts; I slipped my hand in and grabbed a handful of her tight little ass.

The pictures she had sent me before meeting up with her showed just has incredible that ass was.. Unfortunately I didn't get to play with it as much as I would have liked. I cupped it in my hand and squeezed it, massaged it; she reached back and yanked the shorts down just over the hump of her ass and pushed my hand more towards her asshole. She was begging for me to finger her ass but I opted not to.. As that kinda grosses me out (go figure; sticking my cock in there would have been no problem but my finger? Yeah right).

I ran my finger just over the entrance of her hole and I could feel her tremble in ecstasy and still, I opted not to penetrate it with my finger. Instead I quickly swatted her ass and gave her a nice slap; she moaned in pleasure and I could feel the heat from her breath exhale on my cock. I reached up once again and slapped her ass even harder; it echoed throughout the car. This time she squealed a bit but still managed to moan the words "harder."

If you say so.. I continued to slap her ass over and over again, each time harder than the last until she couldn't handle it any longer. By this point I'd had my fun and I had been fighting my orgasm for at least fifteen minutes; there wasn't much else left to do except cum. I laid back and allowed her to do her best and she didn't disappoint. I shot a huge load of cum straight down her throat and she swallowed every bit of it like a champ.

I pulled my shorts up and she returned to her side of the car; neither of us looking over at the other. Her hood was still pulled tightly over her head and face and I awkwardly drove her back around the corner to her house.

"Thanks." We both awkwardly spoke to each other as she got out of the car and I returned home as if nothing had happened between us.

About another month went by until I got the urge again.. It was September 2016. My sexual adventure with tranny's and cross dressers was coming to a close but there was this one girl I matched on Tinder.. She was so god damn hot. Tight athletic body, long toned legs and a perky firm ass. Several pictures showcasing her ass in super tight low cut jean shorts and from what I could tell her tits were just as firm and perky as her ass. I was half right; I thought her short hair was just a good look.. Come to find out she was transitioning and the tits in the pics were just for show (NOT fake tits. unfortunately).

Anyway, she was really hot so I decided to hit her up when I got off work late one night; I quickly learned that she lived right down the street from where I worked at the time. This should have been a red flag but my testosterone had gotten the better of me and I figured what the hell. We chatted a bit and it wasn't long before she invited me over; my next mistake: I didn't negotiate what was going to happen before hand as I ALWAYS do. If you've been reading, you know I always determine and make it clear I'm only here for sex.

I get to her apartment and it's one I've driven by every single day on the way to work; I text her and she comes down to get me. I sat there nervous; determining whether or not I should just flee the scene. This one was risky; she was too close to people I knew in real life and my cover could easily be blown. I stuck it out and went inside.. The situation quickly got worse.

This girls name was Kristen; she was Hispanic and this was not her apartment. She was living with a black family; it just so happened this family had a Transgender Daughter living here as well.. One that I had seen come in to where I work... One that I knew the people I worked with KNEW for a fact; they'd all gone to high school together. I REALLY started to get nervous.

She led me through the front door and up the stairs down a long hallway; the entire family was home EXCEPT for the Transgirl that all my co-workers knew. I was relieved but not for long; as I made my way down to the end of the hallway every door to every room on the way was open and the entire family watched me talk a walk of shame. I heard a large man from one room ask someone "what's going on?"

I assume it was the father of the household; I was a nervous wreck. I didn't turn my head or look in any of their direction; I just wanted to be invisible. Once we were in the room she took a seat at the end of the bed and I sat on the opposite side with a good distance between us; we talked for a long time. Much longer than I'd talked to anyone else I'd hooked up with on this adventure.

She told me about her transition, where she worked, and how she wanted to do a video blog; like her roommate, the transgirl all my co-workers knew. To sum it up: she was talking about a bunch of shit I didn't want to entertain; I was quiet and reserved, clearly uncomfortable but she didn't pick up on it. I came to realize she was looking for the exact opposite of what I wanted; she wanted a deeper connection. I did my best to deflect and tried to make it seem like I was only there in a "friendly' sort of way.

It worked to my advantage until she suggested we watch a movie together; she turns the movie on and turns off the light. Everyone in the house quiets down and I assume goes to bed as it was getting late. I take my spot at the end of the bed she crawls in beside me and begins to snuggle up to me; once again, I've found myself in a position that I REALLY did not want to be in.. And I suffered through every minute of the movie.

I could tell this girl was not like the rest of the sexual deviants I had hooked up with; she was genuine and innocent. I had decided I wasn't going to make a move; hell, I wasn't even sure if she wanted me to make a move. I was just going to watch the movie, thank her for hanging out, and then I'd be on my way.. Well things don't always go as planned.

Half way through the movie her roommate walked in; I'd definitely seen her before. She had on a tight white t-shirt that accentuated whatever she had for breasts (I can confirm she did not have fake breasts but she did have a bra on) and a tight pair of low cut jean shorts. She didn't realize that Kristen had company over and awkwardly introduced herself as we were snuggled up on her bed; she tried to ease the tension and laid flat on her stomach and watched some of the movie with us. I must say this, Kristen had a very nice body.. But it did not compare to her roommate.

Her dark complexion glistened in the dimly lit room and the reflection of the television; she looked smooth as a porcelain doll. She laid there on her stomach and I couldn't take my eyes off her big bubble butt; she bent her legs at the knee and kicked her feet back and forth and her ass bounced each and every time. Perhaps my imagination got the best of me but I ended up zoning out completely and imagined just how great it would be if they were both currently sucking on my cock, together.

Of course that didn't happen; the roommate eventually made her way downstairs to give us some "alone time." The movie ended and I hadn't made a move just yet.. I was ready to go and something came over me; I thought, I drove all the way back out here I might as well get something out of it. Kristen was still snuggled up against my chest with my arm wrapped around her; I decided to just go for it and see what happens. I slid my hand down her back sensually until I reached the waistline of her shorts and slipped my hand down the back; I ran my hand along her firm ass and grabbed a handful.

"Finally.." She said, "I didn't know if you wanted to.."

I didn't even respond and grabbed her by the hand and placed it on my cock which had already gotten hard. I moved her hand up and down the shaft of my cock through my shorts until she took over; Kristen had very nice lips.. But I did not feel comfortable enough to kiss her so we awkwardly groped each other for a while until she pulled my cock out.

"Wow. It's really big." She complimented me.

I thanked her and then said "I want you to suck my dick.."

She was hesitant; she had claimed to not have sucked many dicks in her life and I was inclined to believe her.

"I just don't want to be another sex object for men.." She said.

The arrogance was hilarious in it's own right but I accepted the words she had just spoke; besides I wasn't exactly interested in her myself.

"Alright, it's okay.." I told her.

She paused and stared at my cock; after a few seconds her mouth was wrapped around it. Success.

She got on all fours doggy style beside me and sucked my cock almost in a "69" position except she wasn't on top of me but off to the side. I continued to grope and play with her tight ass as she sucked on the tip of my cock. I moved her down to the end of the bed between my legs for a proper blowjob as she arched her back to show off her ass; with a handful of her hair I pushed her head all the way down until my cock was lodged in her throat. She gagged almost instantly and spit a huge wad of saliva onto the tip of my cock and it slowly trickled down to my balls.

"Sorry." She said, apologizing. "I'm still new to this."

That was quite alright; in fact it turned me on more. I stopped shoving her head down and she continued to put my cock all the way down her throat; she struggled with it over and over but she never gave up. By the end of it, she had actually progressed quite well; I was impressed. When it was time for me to cum she held my cock down her throat and swallowed to massage it as it ejaculated in her mouth; to my surprise she swallowed every last drop.

She handed me a towel and I wiped myself off and got dressed; she walked me back down the stairs to the front door. Her roommate was in the living room watching TV and again, I didn't turn my head to make eye contact. We awkwardly hugged and I got out of there as quick as I could. She immediately began texting me after I arrived home and started to ask me if I'd accompany her to some social outings as a date; I opted to just ignore her messages as I didn't have it in me to tell her otherwise. After several messages to which she got no response she finally gave up.

I spent the next few weeks terrified of what might happen because of this incident; what if she showed up at my work or she started spreading the word around. Luckily none of this ever happened and I only ran into her roommate once, probably six months down the line. She pulled up beside me at a red light:

"Hey, I'm Kristen's friend." She said.

I was a bit confused myself, I didn't exactly recognize her or remember who Kristen was.

"Oh yeah!" I said as if I hadn't completely blown her friend off after fucking her throat for my own personal pleasure. "You live down the street?"

"Yeah." She said.

That was about the extent of our conversation; saved by the green light.

"Alright, well see you later." I said before quickly driving off.

I had been dating a real girl since July and after only two hook ups with TS/CD in the month of August and September, I was aware that the ride was almost over. Over the next couple of months I stayed active on dating apps but I was satisfied with the girl I was dating; I'd message girls, CD's, TS, and so on and I'd even go so far as to make plans to meet up but I never had any intention of following through.

This went on from September until December; I had been leading on the same couple of TS/CD's for a few months, like I said with no intention of meeting up with them. They either lived too far away or weren't hot enough. I'd generally only hit them up when I was horny, rock hard cock in hand, and trying to fuck and it seemed our schedules would never line up that way.

There was however one CD that I was incredibly attracted to; more so than any other person within this sex diary. I had messaged her on and off for months prior to meeting up with her; hell, it took months before she even responded to any of my messages. I was fully 100% convinced that this was just a sexy as all hell natural girl. To my surprise, she turned out to be a cross dresser who was afraid to respond to my messages due to the fact she didn't think I would be interested..

Oh, but how I was; at this point I was pretty much a veteran at taking down some sissy boy pussy. I couldn't tell you how long we talked before we finally got to meet up but it was a LONG time; she was incredibly unreliable. She'd disappear constantly and generally seemed afraid to meet in person.. And she only lived 10 minutes from my apartment! I had to have her.

I remember after she'd just admitted she was a cross dresser I was trying to convince her I was down to fuck still, she said:

"I don't want to get beat up."

Disappointing. I wasn't interested in beating her up for being a CD.. She had the best body I've seen on a TS or CD in real life. Perfect ass, slim waist, thick thighs (but not muscular) and voluptuous plump lips; she wasn't big, quite the opposite really. A small person, probably only weighing around 115 - 120 lbs.. But the ass was thicker than most average girls.

Anyway, after months of blowing me off and bailing on our plans to meet up it finally happened. It was probably around midnight; I was still living with a roommate and couldn't have her over to my place and she lived with her parents. The only option we had was the car, which again.. I fucking HATE. But I really wanted this one.

I jumped in my car and drove around the block looking for a good place for us to fool around in my car; my car isn't very big on the inside and the windows are not tinted. Not exactly ideal for a car hookup; according to her, her car was smaller than mine although the windows were tinted.

I drove to a long street where there were no houses on one side and plenty of places to park on the street; there wasn't much consistent traffic on this street especially since it was already passed 12 AM. But I wasn't sold; I went up a street that led to an apartment complex. There was no gate but plenty of parking space; I drove all the way to the back of the complex, backed my car into a space where I could see every possible direction and parked. I texted her the address and waited for her to show.

...Waited for an entire hour; mind you, this girl only lived 10 minutes from where I did. I was convinced she wasn't going to show; I even texted her to tell her I was going home. Apparently her neighbors were outside and she couldn't leave until they went inside; but alas, after waiting for an hour she showed up.

"I'm here." She said.

"Where?" I asked.

"I don't know, on the street outside the apartments." She continued.

I gave her directions to my location but she claimed she was almost out of gas.

"Just come get me." She said.

I drove out to the street and picked her up and took her back to the location; she got out of her car and into mine. She faced forward the entire time and didn't say a word; generally this is the perfect scenario for me but I was actually interested in seeing her face.. She was truly attractive; face and body. This is the first and only time I ever felt completely compelled and attracted to one of these hook ups.

I parked the car and dropped my shorts; she leaned over from the passenger seat and started to gentle suck the head of my cock. Within minutes I was forcing her head down and making her swallow the entirety of my hard cock; she'd cough and gag and take a second to catch her breath and everything. Come to find out, she wasn't as experienced with deep throating as she had claimed.. Which was fine with me because she was still swallowing my cock perfectly.

She was wearing a dress and much like my last car hook up, I slipped the dress over top of her ass and started to massage it with my hand; this quickly led to me slapping her and rubbing my finger over her asshole. Oh, that ass. My mouth began to water and salivate just looking at it; I'd never eaten a CD/TS ass before but I was fully ready to chow down on this one.