The Hookup

It was three years ago in the beginning of July, only a handful of minutes past 4:00 a.m. when Tom (not his real name) replied to my ********** personal ad that I had posted in the T4M section. I posted the ad along with a few clean but sexy pics an hour earlier, asking if anyone was awake and horny. I had begun to think that nobody was up at this ungodly hour when a few replies came dribbling into my email. I rarely posted ads looking for sex. When I had tried before, they would get flagged and deleted within minutes of posting them, possibly by someone who I had turned down in the past, or perhaps flagged by one of the working T-girls who saw me as threat to their finances. I was hopeful that the late hour would let me slip by unnoticed by whoever was flagging my ads. And I was desperately horny.

The first reply I got was from a young mixed race guy. He wanted to hook up, he said, but it turned out he was not willing to come to me or meet in a neutral, safe place. Instead, he insisted that I show up at his place, and I did not feel comfortable doing that. Certainly not after only a few brief few exchanges with him. He also wanted my mobile number, which I never give out, and I still hadn’t got a face pic from him. I was rather annoyed.

The next reply to my ad was from Tom. He had sent a face pic! He was a cute, very fit 26-year-old living in the next town over, about 20 minutes away from me. So few men are willing to send face pics when they reply to your ad -- it is almost always a dick pic, even when you specifically ask them not to send dick pics. He had a confederate flag with flames tattooed on his chest, but honestly I didn’t even notice the tattoo because I was staring at his yummy six-pack abs. I was a little impressed by his openness to send a face pic right off, too, so another reason I failed to notice the flag on his chest. If I had been paying proper attention, things would have gone differently. (If anyone is wondering if he was racist, he wasn’t. I will get to that later.) I recognized Tom’s pic from an ad that he had posted in the Men Seeking Women section. I recalled that his ad said nothing about him being into T-girls, so naturally I did not reply to his ad when I saw it earlier that night -- I am always considerate of others’ preferences. Evidently, his search for a cis girl had not turned out well, so here he was replying to my ad.

By this time, I was already in my jammies and thinking about taking off my makeup and going to bed. It was getting late -- just past 4:30 a.m. I told him as much, and he wrote, “Ah damn I figured you'd still be looking. I've been horny as fuck all night and could really go for a great BJ right now lol.” I could certainly relate; I really wanted to give a great BJ. I have a huge oral fixation, and giving head is my absolute most favorite thing in the world -- guy or T-girl, it is all good! So I asked him how quickly he could get to me. Perhaps, I told him, if he could get to me by 5:15 a.m., I could see to helping him out. I told him where to meet me, a safe neutral place very close to my house -- a church. I laughed at the idea of this. There is a certain degree of irony asking a guy to meet you in the parking lot of a church. Tom wrote back that he was on his way. He said he would email me when he was almost there.

I changed out of my jammies and put on some jeans, a top and some flats. I checked my makeup and wondered what to do with Tom when he did arrive. I really hadn’t thought this out. My wife was sleeping. She has no problem with me hooking up with men or T-girls for sex, and I usually let her know what I’m up to when I’m being a naughty girl, but I didn’t want to bring this guy inside my house and risk waking her up to have her find me blowing this dude in my basement. That would be rude. Don’tcha think? I felt confident that my wife would be unimpressed by this should it happen. But where to take Tom? I didn’t want to risk anything public either, although the idea of giving him head in the church parking lot appealed hugely! By the time I got his message saying he was two minutes away, I had finally come up with something. I got into my car and drove the short distance to meet him at the church.

It took almost no time to get to the church where Tom had parked, but a hundred different things that might go wrong had crossed my mind during the short drive. I usually take a few days or more vetting someone before deciding on meeting them. I like to get to know people a little bit first, to sort of ensure they are sane and safe. But I hadn’t done that this time, and I was a little concerned. It’s not like I worried that I might get murdered, although, yes, that thought occurred even if it is unlikely. Instead I worried that the person I was about to meet was not the person he said he was, not the person in his photos. And if he wasn’t, then I was prepared to get the fuck out of there before anything could happen. This is why I chose a public spot to meet, in an area that I knew well.

Of course, Tom was taking the same risk as I was. He could not know that I was who I said I was. I have no doubt that was on his mind. Oh, what fun these anonymous meets! Right? But I also worried that he would see me, decide I wasn’t attractive enough, or feminine enough, or that I didn’t look enough like my photos, and leave. Had he been with a T-girl before? Had he even fantasized about it? I didn’t know the answers to any of these questions, and usually I did. I really didn’t know him at all. But he didn’t know me either, so at least we were on relatively equal footing there.

I arrived at the church and saw the only car in the parking lot and pulled up alongside. Inside the car next to mine I could tell it was the Tom from the photos. We rolled down our windows and I said, “Hi. I’m Lena.” He smiled and said hello, nervously. I knew at the moment that it was going to be all right. “Do I look OK?” I asked. Tom nodded. So I told him to follow me.

“Where are we going?” Tom asked.

“We are going to my house.”

I drove back home, Tom following behind me, and opened up my garage door and pulled my car inside. He parked in the driveway and got out of his car as I got out of mine.

He was shorter than I expected, maybe 5’7”, and he wasn’t a large guy, quite slender in fact, but I could see he was very fit, just like his photos. His beard was a bit scruffy, kinda patchy in places, but it was also cute and it suited him. I wondered for a moment if he was into kissing. I love kissing! I motioned to him, inviting him into my garage. As he came over to me, I told him that I couldn’t bring him inside, but that the backseat of my car was more than big enough if he was good with that. Even before he answered that he was fine getting into my car, I could see the bulge in his pants was growing. I bit my lip just a little, and gave his bulge another look, held my gaze just long enough so that he knew that I was looking, then I looked him straight in the eyes and I smiled. I knew he wanted me. And I wanted to get my hands on his body. “C’mon,” I said to him. I pressed the button to close the garage door, turned, and opened the door to the backseat of my car.

Tom got into the car and slid across the back seat to the other side of the car. I got in next to him, put my hand on his thigh and gently traced my fingers back and forth. In my other hand was my phone, and I had a plan for using that, but first I needed to know a few things.

“Have you been with a T-girl before?” I asked.

“Sort of,” he said. “Well, not really been with.... Not all the way. I’ve never done that.”

“OK. What have you done?”

"There was a pretty black trans girl I knew a couple of years ago. And…” He paused, unsure what to say.

“And what? Tell me about her.”

“She was a friend of a girl I hung out with. I never saw her alone, those two were always together when I saw her,” he said. “But one night we were all partying and her friend dared her to suck my cock. I didn’t think she would, but she did. It was like for 20 seconds... and I then kinda freaked out about it. I didn’t want them to think I was gay.”

“All right,” I said, still tracing my fingers on his thigh.

“But I thought about it a lot afterwards. So I’ve kinda had a thing about trannies -- can I say that? Trannies?”

“Yeah, sure. To me you can. I like being called a tranny, but some girls hate it. It’s cool. Don’t worry,” I said in a whisper, and I moved my fingers to the bulge in his pants and gently caressed him until he was hard again. I let out a little moan in anticipation, pleased that our short conversation hadn’t killed the mood for him. “Can I help you out with this?”

I did not hear Tom’s answer to my question, if he answered it all. I didn’t need an answer; he didn’t need to reply. We both knew exactly why we were together in the backseat of my car and what was going to happen. He wanted a great BJ, he had said in his email, and I knew that I was just the girl who could deliver it. I set my phone down onto the seat to free up my hands.

As I slowly unbuttoned his pants, I rested my head lightly upon his chest and drew in his scent. He smelled good to me, the tiniest hint of sweet manly musk, his natural odor. Carefully, I slid the zipper down, my fingers lingering on his bulge for a moment, then easing up to the waistband of his underwear. Don’t rush it, I said to myself. I love this part, the slow reveal. It’s part of the seduction, part of the pleasure. It’s so hard not to rush and so important to take your time. Those precious few moments before mouth meets flesh. I slid a finger under the waistband, then a second and third finger until finally my whole hand was fully inside his underwear. Tom let out a quick gasp of air as I reached my target, and I gave him an approving moan. I could feel the heat from his hard cock as I wrapped my fingers around it. No toy can ever come close to the feeling of a man’s warmth.

He had sent me pictures of his cock in his emails. From those, I already knew he wasn’t huge, and I’m definitely not a size queen, but as I gently squeezed his cock still hidden inside of his underwear, I could tell that he was quite a bit smaller than me. My erection was pressing uncomfortably inside my skinny jeans, begging to be freed from its tight, denim prison, but I ignored that. This wasn’t about me or my cock. I was here to sate his desires, to please him as he required. After all, I am a pleaser. My truest pleasure is derived from knowing that I’m pleasing my lover, getting lost in that moment where the rest of the world fades away into nothingness and there is only the two of us, together, connecting, becoming...

I tugged at Tom’s pants, and he eased his bottom off the seat so I could slide down his pants and underwear with less effort. I slid his clothing down to his ankles and adjusted my position so that my knees were on the floor of the car. Slowly, I ran my hands up his thighs to his crotch, one hand cupping his balls and the other holding the shaft of his dick. I inched my face closer and closer to his erection, and I paused for the briefest of moments to look him in the eyes. As our eyes met, I made my tongue lick the entire length of his cock, from the bottom up to its head, getting it wet.

Tom moaned quietly and closed his eyes, and I took him into my mouth, feeling that first glorious warmth and silky flesh against my lips. He put his hand on my head and forced me to take him in all at once. I hadn’t expected that, and I nearly gagged, not from his size but from the surprise of his cock hitting the back of my mouth before I was ready. I must admit I really fucking love it when a guy does that. Take charge. Make me your cocksucking bitch. I needed this as much as he did. He held my head down for a few seconds, and I forced my tongue out past my lips to give his balls a good lick or two as the head of his cock lingered just past my tonsils.

The pressure from his hand on my head eased up, and slowly I began to withdraw his cock from my mouth, sucking him as hard as I could so that when I had finally released him completely there was a sloppy, wet popping sound from the suction. I darted my tongue all around the head of his dick and took him into my mouth again, squeezing his balls gently and carefully.

I like sucking cock best when it’s wet with lots of saliva, so I raised my head a bit and spat on his erection, watched it dribble down his length and then used my hand to moisten all of his manhood, gently twisting my hand around the shaft as I worked it up and down.

I suddenly realized that I had forgotten something very important.

“So,” I began, “I have this fetish...”

“What fetish?” he asked.

I found my phone on the car seat and held it up. “I like to be filmed when I’m sucking cock. It really turns me on. Would you film me, please?”

“I can do that,” he said.

“Let me turn on the camera.”

I’ve been photographing or filming much of my sex life since I first got access to a digital camera from a job I had back in 2001 or so. That camera used a 3.5” floppy disk to store images. Things have certainly improved since then. Once I started taking pics, I was hooked. I have gigabytes and gigabytes of my homemade stuff, going pretty far back, some of it with me in boy mode with men or women, a lot of it with me as Lena being a very naughty girl. Really, the Internet changed everything and I know it’s partially responsible for my drive to make my own amateur porn. I never watch professional porn. I only watch real amateur porn, which is not very often. But when I do, I love, love, love to watch blowjobs the most. It must be my oral fixation, or maybe it’s that I truly think that nearly every girl, cis or trans, looks sexy as fuck with a big cock in her mouth. And, yes, like many others, I also love it when it when that big cock a girl is sucking is black. So while I haven’t filmed every sexual encounter (because sometimes I forget, or sometimes my lover doesn’t want to be on camera), if I’m sucking anyone’s cock, you can count on me asking to have it filmed so I can watch it over and over again.

Returning to the backseat of my car with Tom, I was delighted that he agreed to film me with my phone while I gave him head. I turned on the camera on my phone and toggled it to video mode. I knew the lighting wasn’t great, with only the car’s internal dome light illuminating the scene, but it would have to do. I gave Tom the phone as soon as it started recording video. He held it on the arm rest of the door as I resumed sucking his cock.

I spat out more saliva and worked it all over his dick with my mouth and tongue while I kept his balls firmly cupped in my hand. I could easily take all of him into my mouth, so I did that often, bobbing up and down on his silky and wet flesh. Then I would change it up and focus on the head, sucking it, using my tongue all around it while my hand would slowly twist around his wet shaft.

“Oh, I do love cock,” I whispered to him. And that is certainly true. For me, there is nothing better. I can suck a cock for hours and not get tired of it, and I’ve done that before. But we didn’t have time for long blowjob session in those early morning hours. The sun had begun to rise, and I had already been awake for almost 20 hours by this point. I went back down on him with vigor, softly moaning as I licked and sucked him. It didn’t take long at all. We had only been filming for just over two minutes when he told me that he was gonna cum.

“Mmm… c’mon, baby,” I said, still working his cock with my hand. I could feel it building up in him, his body getting tenser, and I brought my open mouth to his cock and held it there as my tongue darted out and licked the head. I gave the head another quick suck and jerked him off for a few seconds more. Oh, I needed his delicious cum so bad...

“Ready?” he said.

“Oh, yeah.” I made sure my mouth was open.

He came. His first blast shot all the way to the back of my mouth and coated my tongue, giving me that first yummy taste of his sticky hot cum. His second squirt shot up onto my face, covering my upper lip and a bit of my nose. His cock had slipped just a few inches from my face and there was a trail of semen from the head of it to my lips…

“Oh, yum,” I said, watching more cum ooze out of the tip and down along his shaft. His cum really did taste fantastic, and I wanted all of it, so I immediately put his cock back into my cum-filled mouth to slurp it all up like a truly filthy girl while listening to Tom moan in ecstasy. People might say “cum slut” like it’s a bad thing, but I say it with pride. There’s a real, honest liberation of the self in understanding who you are, accepting it, and ultimately enjoying your true nature. I love cock. And I love everything about cum, whether it’s a messy facial, or having it all in my mouth, sharing it with a kiss, or cum shooting deep into my ass. There is no shame in this, no guilt… no remorse. None of this means I’m a sissy. I’m really not.

I had finished cleaning up Tom’s cock with my tongue and mouth and I leaned back close to him and said, softly, “You taste very good.” He was still moaning a little, and I squeezed the last of his seed out of the head. My mouth returned to his now softening cock to get that last little bit. Waste not, want not.

There was cum all over my fingers, so I licked them clean, enjoying every last drop. There was little more cum still on my face, so I cleaned that up and sucked my fingers clean again. And when I was done, I held Tom’s shrinking cock in my hand, gently massaging it before I once again put it back into my mouth. He shuddered a bit from the post-orgasmic sensitivity. “Oh, you’re sensitive,” I said with a smile, and I eased off him.

We switched off the camera, he pulled up his pants, and we then sat in the car for another 15 minutes and chatted and smoked a few cigarettes each. Occasionally, I would rest my head upon his chest, and I even dared to stroke his patchy beard a few times as I spoke to him. He was quite sweet about it all, and wanted to understand more about t-girls and general trans issues, asking various questions. I answered them as best I could.

We talked a little more about sex, too. He mentioned that he didn’t think he could do anal with a T-girl. While he liked to fuck his girlfriend in the ass, when she would let him, it was a step too far for him to fuck a T-girl. “I’m not gay,” he said. “I don’t know. It doesn’t seem right, I guess.”

I told him that it wasn’t any different than fucking a cis girl’s ass. And I tried to explain that he wasn’t gay if he found feminine T-girls attractive. “You’re attracted to women, to femininity,” I said. But as we got out of the car and left the garage, I was thinking, OK, mission on, Lena! If I see this guy again, I would bet the farm that he would end up fucking me. I just knew it.

Two weeks later, I was at his house, where I would get the chance to find out whether I was right about him fucking my ass.

.... To be continued ....

Pics are from that night...