A New Adventure... Ch. 03

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.

About a month had gone by since my last little encounter with a CD; I'd been on some dates and had some things lined up but nothing was looking too promising. One night while I was at work I began scrolling my dating app and came across a cute, tiny, Filipino tranny; her bio read something along the lines of:

"Visiting from Colorado, only in town for a week. Would like to meet up with some cool people."

And of course, in the "Five Things I Could Never Live Without" section:

"Sucking cocks."

Perfect; exactly what I'm looking for. I shot her a message as I usually do, telling her I'd never been with a TS before and would love to try; it worked like a charm and it wasn't long before we were exchanging texts and pics. She sent over the standard ass pics and some of her getting fucked in the ass; I sent over various gym pictures and a couple dick pics.

Things escalated and I ended up asking where she was staying; she had a hotel room in downtown LA which was about a 25 minute drive from where I lived. We agreed to meet up and I left work around 9:30 and rushed home to get showered up; she was out with friends and said she wouldn't be ready until around midnight.. Which was disappointing because I was ready to go and I hate waiting after getting cock teased all night.

So I convinced her to bail on the club and get ready for me and I was on my way. Downtown Los Angeles can be a nightmare as far as traffic and parking goes; especially because street parking is sometimes unavailable in certain areas overnight and any lot designated for parking can charge a couple of bucks for every fifteen minutes spent parked in the lot. Usually I would pass on a hook up in downtown but I was horny and this one was super attractive.

To my surprise I found parking literally directing across the street from her hotel.

"I'm here." I texted her as I sat across the street awaiting her response; I could already feel the rush flowing within me. My hands were shaking with anticipation.

She responded with the room number and told me to come on up; I was thankful for this. Unlike the very first encounter I had with "L" she didn't have to come down and meet me in the lobby. I entered the hotel and still opted not to even look in the direction of the front desk clerk and made my way to the elevator as if I knew exactly where I was going. I take the elevator all the way up to the floor and proceed down the long hallway; I wouldn't say the hotel was "run down" but it was certainly a "classic" vintage LA hotel similar to one's you might see in an old film noir movie.

Finally I reach her room; she's already got the door cracked and is peeking through. She signals me in and I enter the room; the room was small. Smaller than a small bedroom; it was dimly lit and all the lights were off except for the bathroom light with the door cracked open. She didn't waste time with small talk which is exactly how I prefer it; she started to unbutton my shorts as soon as I entered the room and pushed me back until I was sitting on the edge of the bed.

She quickly dropped to her knees and whipped my cock out and started to gently suck it; she played around with the tip, teasing it and licking up and down the shaft and sucking my balls. I was worried that she wasn't going to be able to handle taking my cock all the way down her throat as she had claimed she could earlier in a text but it didn't take much time before she was jamming my hard cock into her mouth until it was touching the back of her throat.

I sat back and relaxed while she sucked away on her knees like a good little whore; she instructed me to move all the way up on the bed so she could join me. Even better, I laid back and as usual put my hands behind my head to relax as I stared up at the ceiling enjoying having my cock completely worshiped and satisfied. She sucked my cock for at least 20 minutes and I was really enjoying myself.

"Will you fuck me?" She asked.

I could tell I was already getting close to cumming because she had been sucking my cock for almost a total of 30 minutes and it was above the standard run of the mill suck job. I hesitated again but this time it was only because her mouth truly felt so good that I didn't want her to stop!

"Keep going." I commanded.. And she followed the order.

She continued to suck my cock like a pornstar.

"Please fuck me." She begged.

"Okay." I finally agreed.

This girl was a registered nurse at a hospital in Colorado and I had no doubts that she was tested regularly and was clean; she had such a nice tight and fit ass that I was actually hoping I could fuck her raw but she broke out the condom. That's fine, I suppose I remember thinking; better safe than sorry. She put the condom on and lubed my cock up for me before rolling over on her face and laying flat face down with her ass pushed up a bit.

I climbed on top of her and straddled her ass and positioned my cock at the entrance of her hole.

"Slow.." She said, "I'm very tight."

I began to slowly push myself inside of her and she struggled to take my cock; her ass was among the tightest I've ever had. She reached up and threw one of her arms around my neck and pulled me down so that I was laying almost completely flat on top of her.

"Hang on." She said.

I paused as she requested and she started to move her hips back and forth to get my cock inside of her; then she pushed back as hard as she could and my cock slowly penetrated her very tight ass. I was in; this is usually where I'd start pounding away like her ass owed me money but again she was very tight and was still having trouble taking it.

"I want to take it all." She said.

I pushed deeper and started to slowly speed up my thrusts; I shoved her face into the pillow and started pounding harder and harder. She let out soft moans as if she was loving it but also in a bit of pain.

"Harder." She commanded and yes, of course I obliged.

I fucked her in this position for at least 10 minutes before she asked me to cum; I assume her ass wasn't going to be able to handle it much longer which was fine because I was already trying my hardest not to cum. I slowed my stokes way down and softly pushed my cock all the way in until it couldn't go any further before slowly pulling it back out to the tip.

"Cum. Cum inside me." She requested.

But I didn't want to; first of all her ass felt great and I continued to slowly edge myself to climax using her asshole but I didn't want to cum into the condom. That was a bit lame to me.

"I want to cum in your mouth." I told her as I continued to slowly penetrate her.

She begged for the cum in her ass and I had to completely stop moving because I was indeed about to blow my load.

"I want your mouth..' I moaned trying my best to fight off my orgasm.

She reached back and pulled me down again as she had earlier while taking my cock and started to thrust her hips backwards; fucking herself on my cock. This was too much and sent me over the edge and I started to shoot ropes of cum inside the condom. She paused when she felt me exhale during my climax; her ass was so tight that we could both feel my cock twitch inside of her as her ass tightened around me and squeezed every last drop of cum out. I pushed her off and gave her a few good hard thrusts to pound out the remainder of my cum.

I removed my cock and she quickly sat up to remove the condom; she inspected it in the light shining from the bathroom to check and see how full of cum it was. She got off on this for some odd reason and she placed the condom on the bed side table as if it was a trophy. She allowed me to use the shower to wash up and I quickly did before getting the hell out of there.

"Did you enjoy it?" She asked as they always do when they think it's your first time.

"Of course, that was so hot." I told her as I made my way to the door.

We thanked each other for the good time and I was on my way; she returned to Colorado and the last text I remember exchanging with her was something along the lines of:

"Next time you're in town, feel free to hit me up."

Which she was fully okay with; unfortunately she hasn't been back to California since. I would most definitely hook up with her again.

After her, I took a pretty long break from this whole thing and focused primarily on dating girls again. I started this all in December 2015 and by the time I met up with my next CD, it was already August 2016.

Which brings us to the best of the best; though not my personal favorite (we'll get there) but this one does come close in second or third. I found this one when I was going through some stuff mentally; my ex and I had still be fucking every once in a while and she would constantly text me to update me about her life and show interest in me and like a fool I'd play along and fall into her trap. We'd talk for a while and then we'd end up having sex and I'd be convinced she wanted to get back together when really all she wanted was some dick.

The place I was renting my room from fell through and I had no option financially but to move in with a friend on her couch and to top it all off I was working a dead end job that I absolutely hated; the future looked bleak and I couldn't find the solution. Naturally, I turned to sex as the way to ignore all of my problems.

Which is when I met Mia; Mia was a tall, slim, sexy Hispanic cross dresser. She was also a registered nurse like the last TS I had sex with so I felt comfortable with her. She lived extremely close to my apartment at the time but just far enough that I'd never have to worry about running into her; a solid 15 - 20 minutes away, it was perfect.

Much like every encounter before this one, I told her I'd never been with a CD and it was a done deal. She invited me over late one night and I rushed to the car; it was probably 1 AM already. She lived East of LA, a good distance; it wasn't even considered LA county anymore. When I exited the freeway I took one long 2 lane road which is odd for California, it was essentially the middle of nowhere; almost like a country road.

I made a right and proceeded down a long dark road a good distance until I came to a stop sign; I went left down a gravel road, again pretty rare for California (LA at least). As always, I felt the rush of adrenaline; a certain sense of fear. This one was far out away from the city and very dimly lit and secluded, though there were still houses right beside each other; very suburban. Mia was easy; as easy as all the rest so I wasn't too worried, it had become quite common for me now to be in this situation.

"I'm here." I texted her.

"Okay, park a little down from my house and close your car door quietly." She instructed, "Make sure you're open and close the gate slowly and quietly, it's very loud." She continued.

I followed her instructions carefully; she wanted to be as discreet as I was and didn't want her neighbors to potentially see me. I quietly closed my car door and proceeded to the gate which I opened and closed slowly behind me; when I turned around she was poking her head out of the front door. I entered her house and she grabbed me by the hand; she was wearing high heels and was towering over me. She on black fishnet stocks that rode all the way up to just under her ass and a tight solid black silk thong.

She led me by the hand through the living room, through the hallway, and into the bedroom at the front of the house. The living room was extremely dimly lit and the bedroom was pitch black; I don't believe either of us really ever clearly saw the other's face in person. She was extremely nurturing and caring; she believed it was my first time and always asked if I was alright and if I was enjoying myself and so on.

We walked into the room and as usual I dropped my shorts and she dropped to her knees; she took her time making her way up my thighs until she reached my cock. I've never had anyone: girl, TS, CD, boy, sissy, whatever worship my cock the way this girl did. She kissed it, she held it tightly in her hand, she rubbed it against her face and could not stop fawning over it. I felt like a king; she started to gently suck my cock unlike the rest, she didn't barely suck it or lick it instead she took it all the way down her throat slowly as possible. She slid my cock down her throat until it couldn't go any further and began flexing her throat muscles to massage my cock.

Once she was warmed up she placed both hands on my thighs and started to rock me back and forth so that my cock would slide in and out of her throat just a little faster and harder each time. Once we were both comfortable, I placed my hand on the back of her head and shoved it down all the way; once my cock was completely in her throat I started thrusting my hips forward and began fucking her face. Out of everyone I've ever throat fucked I gave it to this girl the hardest.. And she loved every minute of it.

She prided herself on her deep throating abilities so much that in my mind I nicknamed her "Mia the throat fucking slut." It was seriously that good; she loved when I'd fuck her throat as hard as I could for minutes at a time until she couldn't handle it any longer. She wouldn't pull back or try and take my cock out of her mouth; no, she would just let me keep fucking her throat until she coughed very hard and gagged on it. Spit would erupt from the corners of her mouth and completely soak my cock and balls and she'd take a breath and go back in to clean it up.

She also kept a towel on deck for when things got a little too messy and loved to clean my cock before making another mess. She sat flat on her ass and put her back against the wall and signaled for me to come closer; she shoved my cock down her throat and then pulled me by the thighs closer to her until her head was pinned against the wall with my cock in her mouth. She LOVED for me to fuck her throat like this; she gave me both of her hands and placed them above her head as I continued to fuck her throat pinning her hands against the wall so she couldn't move; again, until she would cough and gag.

The first night I went over to her house I must have been there for an hour; it was strictly throat fucking. Once I was done fucking her mouth against the wall she instructed me to lay down on the bed; she climbed up on all fours and arched her back pushing her ass in the air. The silhouette and the outline of the stockings and thong were so hot in the darkness; she had a fat ass. I laid back relaxed while she absolutely worshipped my cock; doing exactly as she pleased with it.

"I love this cock, you have to come back." She'd constantly tell me.

When I was ready to cum she removed both hands from my cock and started swirling her tongue around the tip as she moved her mouth further down the shaft and slowly fucked my cock with her throat; she moved slower and slower teasing me until I finally couldn't take it any longer. I focused on her fat ass that was stuck in the air while she pumped my cock in her mouth and imagined what it would be like to fuck her in the ass; the sensation of her mouth felt just like a pussy and I came for what felt like a lifetime while she gargled and swallowed down every last drop never stopping once from her slow throat fuck.

I laid there in complete ecstasy; I have a very high sex drive and my cock almost never goes soft after I cum so she continued to play with it and suckle on the head of it. She started using her hands again and completely revived my cock if there was any chance of it softening (there wasn't). She started to increase the twisting and stroking with her hands while taking it in her mouth; again at a decent pace, never too fast. (I personally can't stand super fast handjobs/blowjobs, I like to feel every last inch of my cock going down the throat)

"Fuck, you're going to make me cum again." I told her.. And this was only about five minutes after my last orgasm.

My cock was still hard after the second orgasm and she attempted to continue; I was exhausted and opted to call it at night at that point. She gladly cleaned all the spit from my cock with her towel and allowed me to wash up in the bathroom before I was on my way. I was nervous to return because I actually enjoyed it so much but deep down I couldn't wait to come back.

It took about a week or two before I was desperate for a good throat fucking so naturally I hit Mia up again; it was late like the last time and our second encounter was much like the first except this time when I arrived at her house she met me outside the front door. I opened and closed the gate behind me quietly as instructed and turned to find her right there on the front porch on her knees; I walked up to her and she yanked my shorts down right there outside her house.

My cock was rock solid before my shorts hit the ground; I grabbed the back of her head and shoved it down, holding it there until she gagged on it. She continued to throat fuck herself on my cock and pinned me up against the side of the house as she used my cock for her pleasure; she informed me that she had someone visiting and staying over night so she snuck me in through the window of the room in the front of the house.

Once we were inside it went almost identical to our first encounter; just a few solid hours of some good old throat fucking. I've still to this day never met someone who enjoyed gagging on cock for literal hours at a time except for her. I laid there with my arms behind my head, kicked back and relaxed yet again; Mia was on her knees between my legs with her back arched like a good girl and her ass in the air for me to admire. I started to fantasize about how good it must feel to have her tight ass wrapped around my cock; her fat ass cheeks bouncing off my thighs every time she pushed back on me.. I soon came to climax not long after.

"Next time.. When I have more time to prepare." Mia would tell me as I was leaving her house. She knew just how badly I wanted to get inside of her tight little hole.

Only a few days later I got the text; tonight would be the night. She was ready and waiting for me to come through with my hard cock one more time. I left my house around midnight as usual and anxiously drove to her house; she met me outside again and sucked my cock on the porch. Mia took my by the hand and led me inside, she was wearing high heels again and a tight black thong with her fishnet stockings.

Into the bedroom we went; she climbed up on the bed on all fours and looked back at me as I stood behind her. She pushed back and rubbed her ass against my hard cock; I began slapping her ass and gently biting it, she shook her big ass in my face back and forth teasing me. Before I knew it she had flipped upside down and was laying with her head hanging off the side of the bed with my cock lodged in her throat.

I grabbed a hold of her bra which held her fake breasts (not breast implants, more like a fake breast/bra set) and started moving my hips back and forth as if I was fucking a nice wet pussy. Her mouth was leaking spit all over the place and she did her best to please me by not gagging and allowing me to have my way with her throat as roughly as I pleased.

"Are you ready?" She asked.

Of course I was ready; it was time for the main event, my heart was pounding and my blood was pumping. I was ready to tear that sweet ass up! That's when she pulled out the condom and my excitement started to fade.. But only a bit. Mia was also a nurse so I was sure she was clean and I was looking forward to fucking that ass raw but as always, better safe than sorry!

She rolled the condom over the tip of my cock and then used her mouth to roll it all the way down my shaft; she turned around on all fours and sat on the edge of the bed just as she had earlier when she was teasing me. She pulled her thong down just under her perky ass cheeks, keeping her cock and balls covered; she began lubing her ass and my cock. She grabbed my cock with one hand and pulled it close to her asshole and lined it up with the entrance; slowly I pushed forward until the head of my cock breached her tight little hole.