How in the world do I get myself in these situations? I guess I really can’t say ‘these’ situations because this certainly isn’t something that happened to me before, let alone often. I do have to wonder if it's ever happened to anyone before!  I can honestly say I made some choices that … didn’t work out the way I had thought they would. It started out simple enough, I met a girl!

Although, since then she has told me to refer to her as a ‘gurl’ because she is trans. Maybe that would be obvious to you, but it wasn’t to me.  I thought it was strange when she spelled it out, because it sounded the same to me.  But once I understood what she meant, it made perfect sense.

I've also learned a few things like never, ever use the term ‘shemale’ or I might find myself missing an appendage that I really liked. She preferred ‘trans’ or ‘transsexual woman’ or simply refer to her as a woman and she was happy. In fact, she said one of the reasons she was attracted to me was I treated her like a lady and, aside from peeking down her top when given the opportunity, I was a gentleman.

We met at lunch in a small pub. It was crowded and she asked if she could share the table I was at with a work buddy. We, of course, said yes. I mean what guy isn’t going to want to share a table with an attractive girl! She was certainly attractive, a real knock-out.  Tall, well-built, gorgeous dark hair, phenomenal butt, and really long legs.  The cleavage she showed didn't hurt our feelings either.  I saw a few glances from other people and all I could think at the time was they were jealous she joined us.

The three of us had a great lunch. Not only was she seriously beautiful, but she had a wicked and raunchy sense of humor. I know my friend was trying to extend lunch as long as possible, but he had to return for a meeting. I called out the rest of the day and … well, long story short, we ended up back at her place where I discovered her ‘difference’ and with a bit of coaxing on her part, I did some things I never thought I would ever do.

Seriously, we were kissing so hot and heavy in the elevator I was afraid I was going to stain my slacks. She was wonderfully aggressive and certainly knew what she wanted. Once we got in the door of her apartment, she had my shirt off before I could blink. I’d never had a girl suck on my nipples before, but between that and her rubbing me through my slacks I was as excited as I think I'd ever been, that’s when she slowed down. She took off her top, showing off a great set of breasts, but then she hesitated to take off her pants, I thought she was having second thoughts. Turned out she had a little something to show me, well not so little a something.

I didn’t sit there like an idiot gibbering, I just stared at it while she stroked it and it slowly got hard. Some part of me did say "Run!" at least I tell myself now that it did.  But I wasn't listening to that mental voice.  I think my penis was also shouting to drown that voice out.

I know she was talking, but for the life of me, I can’t remember exactly what she said. When I didn’t go running from the room, she pressed against me again and started kissing me with much more ardor, if that was possible. When her hand grasped me and she found I was still stiff, she smiled and pulled me into her bedroom.  She all but threw me on the bed and her pants disappeared along with anything else she had on.  She looked like the perfect woman, just with something a bit extra.  I was still trying to get my head around it, but she wasn't waiting.

While the feeling of her cock against me was weird, we actually made love like it didn't matter. She went down on me and teased me to the point of cumming, although instead of handing me a condom or asking if I had one, she pulled one from her nightstand drawer, opened it, and put it in her mouth. One quick head-bob and it was on my cock. I had a feeling she certainly had done that a few times. She pulled me on top of her, her legs spread and her knees were pulled up almost to her chest. With one hand she guided me to her ass and I sank into the warmest, tightest … well … pussy I had ever felt. I know intellectually it wasn't her pussy, but it felt like one, a real tight one.  I once made love with a virgin and this girl was even tighter!

I’d done anal before too, but no one ever felt like her. When she tightened her muscles, I couldn’t believe the feeling. She didn’t talk anymore, there was nothing left to say. I knew what to do from here, and you might call it making love, the reality is we fucked! We fucked for as long as I could hold out and I swear I thought about some of the least sexy things to hold out. I wanted it to never end, no one ever felt like this, so sexy, so aggressive, and even so experienced. She was nothing short of amazing. I came in several shudders that went through my entire body. When I collapsed on her, I could still feel her own still hard cock against my belly.

We took several minutes to recover and she even removed my condom and took it into her bathroom for disposal, much like a girl would have done to clean herself if we hadn’t used one. But that’s when things took another strange turn and we both heard a voice through the bedroom door.

“Honey, I’m here before heading home, are you decent?”

My new — well I guess I can’t call her my girlfriend, although I had been thinking along those lines because she really was amazing — my gurl-friend called out, “Give me a minute. You should have called, baby.”

The voice, a deep one that seemed to be coming from the bottom of a very large barrel, said, “I know, but this was a last-minute thing and I wanted to see you.”

“Alright, just give me a couple of minutes.”

She held a finger to my mouth and whispered, “Just go with it. He’ll freak if he finds me here with another guy. It’ll be okay if you keep your head on straight.”

I was reeling from the mental punches I had already taken when she tugged on a pair of her panties, the ones she had been wearing. But she tugged them on me, not herself. She sat me down at her make-up table and slapped a wig on my head and took a few seconds to paint both of our lips with some reddish lipstick. It felt really weird, like a thick layer of lip balm.

“Just stay here no matter what happens. I’m going to tell him you are a friend of mine transitioning and needed some help.  He'll be okay with that.  Just stay right here and everything will be fine, he’s really a decent guy as long as he doesn’t know you are a guy.”

I froze there, not sure if I should just jump out the window or not, but being five stories up made that very silly idea. She shrugged into something very thin and a bright pink and opened the door. In the mirror, I saw a guy, but he wasn’t as big as I was expecting because he didn’t fit the deep voice.

“Hi, baby. I said you should have called because this is Tina, she’s a friend of mine and she came by for some tips and tricks. She’s just starting out.”

He came over to me and put his hand on my shoulder, “Tina, it’s a pleasure to meet you.”

I mumbled some sort of a response, to which he laughed. “A shy one I see, Tess.”

“Well, as I said, she’s just starting out. You’re probably the first guy to see her even partially dressed, let alone sitting in panties.”

He laughed a booming laugh and then turned his attention to Tess, which wasn’t the name she had given me, but who cared at that point. I was frozen stiff, scared, and felt my heart going about a thousand miles an hour. I mumbled something like I would go wait in the other room, but he stopped me.

“Sorry, Tina, a couple of my guys are out there. They might get the wrong idea. You are safer in here with us. You can join in if you want?”

Thankfully, Tess killed that idea, “No, she’s not that far along yet.”

His eyes lit up, “A virgin?”

“Exactly! When I said she was just starting out, I really meant it.”

He looked at me, I could see his face in the mirror. “Well, honey, when you are ready to take things a step further, I would love to be your first.”

Tess smacking him on the shoulder, “You aren’t going to have any energy left for her once I get done with you!”

With that, they tumbled on the bed and … not to go into details, but with me, Tess was the leader, with him she was definitely the follower. I could see some of the activity in the mirror, but I tried to just sit there and remain as inconspicuous as possible. It sure sounded like the two of them had a good time.

What felt like hours, but was only about thirty minutes or so, the couple finished with a loud groaning flourish and he kissed her and got up.  He came over and patted me again on the shoulder again, his cock limply hanging there in the mirror. “Don’t forget me, Tina.” He looked down and then said, “I think you are closer than you think.” My eyes followed his gaze and I saw a cum stain spreading on the front of the panties. I hadn’t even touched myself!

“I don’t think I ever could forget this,” I said as honestly as I could. No, there was no way I would forget, this was weirder than having a husband come home early — which only happened to me once. I didn’t even know she was married. I count that as the weirdest thing ever — before today anyway.  It was weird because they planned it and he wanted to join in.  The unexpected swings caught me off guard.  I mean one second you are really enjoying yourself, then you are in a panic when you realize not only she's married by husband came in the room, and then you discover he's bi and wants to join in.  I panicked and left! 

As I was remembering that Tess' boyfriend got dressed, I simply prayed like hell to get out of there with my sanity and my nuts intact, but I was still having doubts. He smiled at that and went on his way. Tess breathed a deep sigh of relief when she heard the outer door close. She came over and hugged me while I tried to get my body to unclench. “You did great, baby! He never suspected a thing.” Then she too looked down and grinned. “I think you must have enjoyed that more than I thought you would. Guess I’ll have to wash those panties out.”

I finally stood on shaky legs and she stripped them off of me, then balled them up and stuffed them in my mouth. “God, having you here was such a fucking turn-on. I was so scared and also fucking excited I thought you were going to give everything away, but you are a kinky little slut like me. She pulled me back to the bed and put me on my hands and knees and started eating my ass.

That was new, no one had ever done that. It felt weird but no weirder than everything else that happened this afternoon. She didn’t ask, she just went at it and it started feeling really good really fast tonguing my ass and stroking my cock like she was milking me. She got me all wet, spit on my asshole, and then I felt her shift.

“He’s great and even pays for this place for me, as long as I am available. But he hasn’t made me cum in months and right now I am so turned on!” She put her cock to my ass and slowly pushed it in. “That’s it, my kinky baby, you are going to love this.”

I was expecting it to hurt, but it really didn’t. I just felt like I needed to take a ... well you know what that feels like.  It was uncomfortable, but it really didn't hurt.  Her body was so warm against me, but shortly it started feeling even better. I actually felt her cock get harder and felt my own respond. Today was a lot of firsts! I came again, spurting on the sheets that smelled like her and, I guess, him. Then she pulled out and I felt empty.

“Turn over!”

She started jerking her cock and shortly came on my face, something I never did with a girl myself and certainly never had it done to me. Yet another first in a day loaded with them! She laid on top of me and started licking her own cum off my face while kissing me. It should have been gross, but it was about the sexiest feeling I ever had. Her body was sliding all over me while we kissed and licked each other’s faces. It was the weirdest yet most incredible experience of my life, but I knew it was a one-time thing.  I couldn't even think about repeating it, especially the scary part about her … boyfriend.

So, after I left, I did what any ‘normal’ guy would do and tried my best to put it all behind me, that was until today…

“Andrew, can you bring in the Harris account file.”

That’s me, Andrew.

I’m an executive assistant who gets treated more like a glorified secretary, but it paid well. I had the Harris file on my desk because it was a new client and I knew they were coming in. The meeting was scheduled for one, so I made sure I was back before then, but I guess they were early because they were already in my boss’s office when I got back from lunch fifteen minutes early.

I knocked once and went right in. That was the normal protocol. As I opened the door I heard a sound that nearly made me piss in my pants, a big booming laugh. Sitting there was Tess’s boyfriend, chatting with my boss. I brought the file in and gave it to David, my boss.

“Carl, this is Andrew, my assistant.”

“Pleased to meet you, sir.”

As we shook hands I knew he couldn’t possibly recognize me. He mostly saw me from behind and in a mirror while I was almost naked with a blonde wig and a garish red lipstick. I slowly let the breath I didn’t know I was holding as those thoughts finally percolated through what was left of my brain. I think I just did a complete cardio workout in about ten.

I left the office knowing David would have me handle any details later. I sat back at my desk and tried to regain my sanity. After about half an hour, Carl Harris came out. He and David shook hands and as he turned away, David gave me a high sign and five fingers which told me to give him five minutes and then come in to deal with the paperwork.

As Mr. Harris passed my desk, he slowed and looked at me, then my cardio workout started all over again.

In a quiet voice, he asked, “So how is the transitioning going, Tina?” He actually seemed curious, but my panic rose again. “Tess told me you had second thoughts, but I think that’s a shame. I believe people should never back down from something just because it’s hard. Go visit Tess again, we both would love to see you. Tonight about six.” He smiled sympathetically, but his tone broke no argument. My cardio workout went into overdrive. Then he patted my shoulder for the third time and headed out.

I sat there at my desk, trying to figure out how things got so out of control.  My head was spinning, then without realizing it, I found I had to adjust myself because my traitorous penis was hard as a proverbial rock!