tagTransgender & CrossdressersA New Adventure... Ch. 02

A New Adventure... Ch. 02


This is a continuation 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 first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with girls and everything was back to normal.. However it wasn't long before I was sucked back in.

With a little experience under my belt, I had come to the conclusion I would keep having sex with these random CD's and Tranny's but under a certain set of my own personal rules. To sum them up:

- I would always predetermine what was going to happen before I left my house.

- I would under no circumstances kiss them.

- I always made sure to keep the lights off/room dark.

- I NEVER touched their cocks and rarely even saw them (they usually preferred it this way as well).

Now, back to our regularly scheduled program.

I started dating a really nerdy girl who looked similar to my ex, body type and all; this only lasted about three weeks because she was by far the least interesting person I'd met in some time and the sex was among the worst I've ever had. I stopped seeing her and returned to the dating apps in search of more cis-girls but the temptation of seeing ready and willing CD's and trannys is a lot to handle when you're just trying to bust a nut.

I came across one Hispanic women in her early 30's, she was pretty attractive and had some large titties; so naturally I shot her a message. We chatted for only a few minutes before she started escalating things which is odd to say the least, considering that's uncommon for women on dating apps. Well come to find out, she was a tranny; I don't remember the exact exchange but it went similar to this:

"I am a tranny."



"Okay, I'll fuck you in the ass then."

English was not her first language and I threw that last line out there half joking just to see what she would say. To my surprise she was positively receptive of such a response but I wasn't sold yet; I was always very cautious when arranging these hookups. I was pretty worried about being scammed or catfished, robbed, beat up, etc.

I dropped her my phone number and she started sending pictures of her naked; she did indeed have large fake breast implants and looked like a genuine woman. She sent videos of her sucking dick and getting fucked from behind but she still seemed a little strange. I opted to not meet up with her right away and actually stopped talking to her shortly after within the same night.

But as we all know temptation only grows as the nights go on; so about a week later after scrolling nightly with no girls in line for dates I decided to message her again. It was already pretty late, probably around 2 AM so I quickly set everything up and committed. She lived with her mother and couldn't bring me in the house so she suggested car sex; however I hate car sex but I was going to take whatever I could get at this point.

She sent me her address and she lived about an hour away (this is pretty common in Los Angeles, to drive an hour just about anywhere). She continued to text me on the way there:

"Will you fuck me?"

"Do you want me to eat your ass?"

Of course I wanted my ass ate but I wasn't sure about the fucking just yet; I still hadn't had sex with anyone that had a penis.. But she was pretty hot.

I arrived at her house around 3 AM; the way her house was set up was a bit strange but pretty common in LA. It was tucked behind a liquor store and behind the liquor store was another house and behind that house was her house; there was also another house behind hers. All the house and the liquor store shared a long common driveway; one entrance for each.

"I'm here." I texted her.

"Okay, park in front of the liquor store and I'll come get you." She responded.

I sat in my car in front of the liquor store and I could feel the nerves beginning to rise within my stomach; the adrenaline was flowing and I was almost shaking. I was just hoping she was as attractive as she looked in her pictures and was real. A car pulled up beside me and I got out, locked my car door behind me, and got in. I got a quick glance at her and faced forward, trying to keep her from really seeing my face.

She drove down the long driveway, passed the liquor store and passed the first house. She parked in front of her house and immediately reached over to stick her hand in my shorts; she grabbed a handful of my cock which was all but rock hard already. She stroked it for a bit before pulling it out of my shorts and leaned over to start sucking it.

"Let's get out." She said, after sucking on my cock for a bit.

I didn't ask questions, I just followed her lead. We got out of the car and walked around to the side of it so that we were behind the car facing the driveway; she dropped to her knees and pulled her shirt up over her fake tits and started deep throating my cock to show off her skills. I reached down while she sucked my cock and grabbed a handful of her fake breasts; they were incredibly well done. I had never been with a girl who had fake tits before and still haven't as of now, except for her. As things progressed I got more comfortable and aggressive and grabbed the back of her head and pushed it all the way down until I could feel my cock in her throat. She coughed and gagged pulling back to catch her breath but quickly grabbed the back of my thighs and pulled me in taking my cock all the way back down her throat to the balls.

"Will you fuck me?" She gasped in between breaths while I was fucking her throat.

"I don't know." I responded, shoving her head back down on my cock. "I didn't bring any condoms."

Much like the last time I used this excuse, she informed me that she had condoms and asked again. I hesitated and told her I'd never done it before; sure I'd fucked my ex in the ass more times than I could count but never someone with a cock. She ended up convincing me to go through with it; I was only 23 at the time and she was at least ten years older than me so I really felt comfortable with her. I trusted her.

"Wait here." She instructed as she went back in the house to grab a condom.

My heart was pounding as I stood there with my shorts around my ankles in an alley way waiting for a tranny to come back so I could fuck her in the ass; this was the exact kind of sexual depravity I was searching for. She came out of the house and dropped to her knees once more for my pleasure; after sucking my cock and getting it nice and wet she put the condom on for me.

For good measure she went deep on my cock again with her mouth and got the condom nice and wet, spitting as much as she could to lube it up for her ass.

"Be careful, I'm very tight. I don't get fucked alot." She said, as she stood up turning her back to me.

With her back turned she pulled her pants down to her knees and bent over the hood of the car; she pushed her ass back until it was up against my cock and reached back to grab it. She spread her ass and lined my cock up with the entrance of her hole and pushed herself back further to slowly get me inside of her; she took a quick break and spit on her fingers and then rubbed the spit around her asshole and slipped a finger in to loosen it up.

Just as I was about to fully enter her we saw headlights approaching us down the long dark driveway; one of her neighbors that lived in the house behind hers had to drive down right by where we standing and about to fuck.

"Get down." She directed me.

We both ducked down beside her car as her neighbors car drove right by us, merely feet away. Luckily they didn't see us or suspect a thing; we waited until we heard the car door close which was followed by their front door. The coast was clear and it was time for me to fuck my first tranny.

We got into the same position where she was leaned over the hood of the car backing her ass into me; after a few minutes of slowly pushing my cock inside of her tight hole I was able to start pumping in and out of her. Once she was completely stretched out the real fun began and I started pounding away; she pulled her shirt over her fake tits again and threw one of her arms back over my head. She grabbed the back of my head and pulled it in close to her breasts and made me start sucking her nipple; I reached around with my hand and firmly grabbed her other tit while continuing to suck on the one she put in my mouth. I pounded away at her ass, which was just as tight as she said it was; unfortunately she couldn't take too much abuse in her ass and couldn't last for very long.

(I personally am not a fan of condoms and prefer not to use them when I have sex at all; especially if it's with a girl but given the stigma of STD's in the gay community and on the account of the randomness of the hookup, it was best for me to keep it safe. Not saying that gay people are more likely to have STD's than girls are but I generally get to know people more before fucking them.)

"Cum! Cum inside me." She asked.

I wasn't exactly ready to cum but could tell she wasn't going to be able to handle it much longer, so I pounded deep and hard until I shot a huge load into the condom. I kept my cock buried in her ass as she held her arm around me tightly with my head nestled on her big fake tits. I slowly pulled out of her ass and as soon as I did, she turned around and dropped back to her knees; she stripped the condom off and cleaned up any cum that was left on my cock.

Unlike my first encounter with a TS, my cock was still rock hard after cumming as usual; so she continued to keep sucking it. I wasn't too interested in continuing as the sexual desire had faded but once she started gagging on my cock I couldn't help myself. I grabbed her hair and pulled her back forcing her down to my balls; she started sucking on my balls and I started stroking my cock as fast as I could to work up to another orgasm. Fortunately I'm very good at cumming back to back and in no time at all I was cumming again.

I shot my second load on her pretty brown face and all over her lips before she took my cock in her throat and swallowed the remainder of the cum down. She cleaned my cock with her mouth and scraped the excess cum from her face into her mouth; I pulled my pants up to be on my way. She started making a bit of small talk so I hung around not to be rude but these exchanges were always extremely awkward for me.

She thanked me for coming and asked if I enjoyed it; I told her it was great and she hugged me tightly. I could tell she was starved for attention and probably didn't get alot of sexual intimacy given the fact she has a cock; she seemed genuinely happy. This unfortunately did not sit well with me and made me very uncomfortable but like I said she was very nice so I made sure to treat her respectfully. Given the way she acted towards me post-sex was all I needed to convince myself not to return to her a second time.

A month went by and after a few random hookups with girls; I needed something a little more depraved once again. This next little sissy boy was a cross dresser who actually had to active profiles on the dating site I was using; one was him dressed as a girl, openly admitting he was a sissy CD, the other was just advertising his glory hole. I messaged both and soon found out they both belonged to him; I went with my usual "I've never done this before.." and that was that.

She was tall and had very long legs, there were no full pictures of her face just the lower half with her lips; her lips were very nice to say the least. The other pictures were full body, dressed in some sexy black lace lingerie; I was already sold. She told me how she loved to suck cock at her gloryhole and preferred it be an ongoing thing; she told me she had a guy who would regularly come over before and after he went work to fuck her throat and even sometimes her ass.

I really never had done a gloryhole and I wasn't really interested in trying it; so I opted for my usual. I told her I'd prefer to be able to lay down and get comfortable and that if we kept the room dark I would have no problem not using the gloryhole. She was fine with this and it wasn't long before she sent over her address; she lived downtown which was a hell of a lot closer than the last one.

Parking can be inconvenient downtown so I made sure to clear that up before leaving; it was strictly street parking but there was plenty to choose from. I parked a good distance down the street from her apartment and sent her the text. I awaited her response and instructions and proceed to walk down the street towards her place; much like the last encounter her apartment building was awkwardly tucked behind another.

Down the sidewalk I went behind the first apartment building, there was a doorway leading inside the second apartment building; the door was open and the hallway was long and dark. The apartments themselves did not look very nice on the outside and were borderline run down/ghetto so I was admittedly nervous as usual.

"Where do I go?" I texted her, hoping for some better direction.

Of course the answer was through the doorway.

"First door on the right." She added.

Her apartment was quite literally the first door on the right as soon as you entered the dark hallway, though I still wasn't sure I was in the right place. I stood in front of the door and debated whether or not I should knock; she had instructed for me to let myself in. Well, there are few things more unsettling than not knowing if you're about to enter the right apartment or not so I stepped back outside the building as the apartments weren't labeled or numbered.

"How can I tell if I'm at the right place?" I asked.

She responded by signaling me with the light outside of her apartment door; on and off and on again. That had to be it. I opened the door and it was pitch black just as we had discussed; the light from the street shined through the curtain and as my eyes adjusted I could make out the outline of her body. She was already sitting on her knees waiting for me in the doorway to her bedroom; where the gloryhole would usually be set up.

"Hey.." She said as I approached her; she didn't hesitate to grab my cock which was already hard through my shorts. I dropped my shorts to my ankles and she grabbed both of my legs and pulled herself close to me until she was literally swallowing my cock; she continued to pull and push me back and forth jamming my cock into her throat harder and harder each time.

One thing that she had forgot to mention was, she loved to be used; she preferred it. She loved it when she felt like an object who's only purpose was to make someone cum. This was great for me because I love rough sex; once I got the hint I grabbed her by the hair and pulled back to start violently and aggressively fucking her face. She spit and coughed and gargled bubbles of spit all of my cock; I pushed her backwards onto her ass so she was now sitting in her room without ever removing my cock from her mouth.

She backed all the way up to her bed frame and sat straight up against it so she couldn't run away from my cock any further; I slowed things down a bit and made sure I could feel every inch of my cock slipping and sliding down her throat. She continued to spit and couch and gag over and over again without ever stopping for a break or to catch her breath.

She jumped up and laid down on her bed with her head hanging off the edge of the bed, upside down and I moved in closer to fuck her throat this way. She pushed me back and told me to turn around so I did as asked and when I did she grabbed two handfuls of my ass and spread it; she buried her face in my asshole and started to lick my ass just as aggressively as I was fucking her face.

She asked me to lay down so I could kick back and relax as we had discussed and she continued to fuck her throat never slowing down or tiring once. She turned around so that her ass was facing me and started grinding her nice, toned and tight ass up against my shaft while running her hand up and down it.

"Should we fuck?" She asked.

I hesitated again but quickly gave in as her tight ass grinded against me.

"I don't know. Will you ride me?" I asked, playing "I've never done it before" card as always.

She quickly leaned over and grabbed lube from her night stand and slicked my cock up; before I knew it she was turned around reverse cowgirl style and was taking my cock deep in her asshole. This was the first time I ever fucked someone with a cock raw, with no condom; it happened so quickly I didn't have time to think about it. She had mentioned she was on PreP and got tested regularly, so I didn't worry about it too much.

Her ass was even tighter than the last one; by far the tightest ass I've ever fucked.

"Slow down, you're gonna make me cum." I told her.

She got off my cock and fell forward onto her hands and knees with her face down and ass up; my favorite position. I got behind her and thrusted my cock deep into her tight ass, which hadn't stretched or loosened it's grip at all; unlike the first girl she could take a pounding. Except this time, I had face fucked her for damn near 45 minutes and the tightness of her ass was too much for me handle; I pounded away as hard as I could for probably five minutes before I couldn't take it any longer. I came deep insider her ass and filled her up; perhaps it was also due to the intense sensation of fucking her in the ass raw.

I was exhausted; I collapsed on the bed beside her after pulling out, face down. It was only mere seconds after we had finished having sex that she insisted on giving me a back massage. Any other time I would have declined and would have quickly been on my way but I was so sexually satisfied and worn out that I just laid there and allowed her to massage my back. She finished things up and told me I could use the shower if I needed to, so I washed up and was on my way.

On the drive back home I had come to the conclusion that things got a little too "close" and uncomfortable once again with the back massage and all and I decided I would not be returning again.. Until the next time I got uncontrollably horny and needed to take my sexual aggression out on someone.

The second encounter was almost identical to the first; it was probably around 10 PM and I had felt the urge building inside me to fuck something. I hit her up and she asked when I'd like to come over; as soon as possible, I told her.

"Give me an hour?" She asked.

"I'm leaving right now, I'll be there in 30." I told her.

"You're killing me lol" She texted back.

But I didn't care; she was an object made to be used and I was going to take advantage of that. I needed to cum immediately; when I got to her apartment, I made the long and dark walk back to the door. It was left unlocked again just like the last time and she was sitting on her knees in the doorway, just waiting for me to destroy her throat. After a long session of face fucking I hopped on the bed and laid back so she could continue to worship and choke on my cock.

Something hit me in the middle of her gagging on my dick and I had to have her ass again which we did not discuss prior but I didn't care. I yanked her on top of me and sat her on my cock; she wiggled her ass around the tip of my cock to work it inside of her before she sat all the way down on it cowgirl style. I pulled her head down and held it just over my shoulder by my head as I thrusted my hips up from the bed and shoved my cock deep inside her; I continued to pound her in this position until I filled her ass up with my cum yet again.

I was 100% satisfied this time; it wasn't until I got back home that she mentioned in passing she had already been fucked in the ass once earlier in the day and that's why she was ready to take it from me. While in theory this is pretty hot, it completely freaked me out since this was real life and not porn and that can be kinda risky and dangerous; this time I really made the decision not to return.

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byjohnjinglez1© 0 comments/ 11226 views/ 7 favorites

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