It was 1984, I was 18 and had just quit college. School just wasn't where my head was...never was. It's not that I'm dumb, just too restless for classes and instructors. Having always been a musician, I thought I'd try my hand at just gigging full time.
Needless to say, the money wasn't too great playing in bar bands but it kept money in my pocket, a roof over my head and food & beer in me! I had found a cheap apartment in the downtown section of the small Ohio town I lived in. There was a little corner bar and a convenient store just two blocks away. The street between there and my apartment was where the local "gay bar" was located. I had passed there many times en route for cigs or a 6 pack (or 2 or 3 haha). I often noticed a lot of black "transvestites" would be out and about as soon as the sun went down. I had secretly had a "thing" for the "third sex" ever since I was 10 and had seen pictures from the Rocky Horror Picture Show in a copy of Newsweek. And here they were! In my little small town in Ohio! And what the...? They were coming up and propositioning me!
OK...a little about me (at the time! LOL). Like I said, I was 18, about 5'8'', brown hair cut kinda spikey (as was the look at the time)...usually wearing black t-shirts and tight Levis straight leg jeans. I was in good shape with broad shoulders and a good sized chest and arms. I worked construction in the daytime too...the music biz was never too hot in Ohio!
Well, one night, after way too many beers, I'd gone out for a walk. It was a warm Indian Summer night. Probably in the mid to upper 70s at damn near midnight. I'd been just walking around...drunk and bored and finally just plopped down on a bench near the bus stop. I just sat there, smoking cigs and watching the cars and occasional pedestrians go by.
At one point, this tall, long legged GODESS in high heels and a short, white open backed dress comes walking along. I musta looked like a hungry dog staring at a butcher's window because this vision caught me staring, turned and came back! UH OH!
Turns out I was sitting 2 doors up from the gay bar! Well, this gorgeous hunk of womanhood introduced herself as Tiffany and asked me if I'd like to join her for a drink. Well, being an all American red-blooded lad of 18, I thought, HELL YES! We went into the bar but the wouldn't serve me as I was obviously a bit wasted already and since I didn't have my ID with me, they weren't gonna take the risk. Ohio always had some weird liquor laws!
I figured that my chances of scoring were zero-nil at this point when all of a sudden, Tiffany suggest we go back to her place for a drink instead! Well, ya coulda knocked me over with a feather! Hell yes I'd be more than happy to join her at her place for a drink! I have to admit, that I was, as usual for me, horny as the day is long! And having always been a leg man, I was just about in heaven!
Tiffany's legs were about the sexiest I had ever seen! Long long long brown legs, shaved smooth, toned and very shapely. They rose up to one of the most perfect asses I'd ever seen! A lot of black gals have either too much butt or it just sags...not Tiffany though! This was perfect! Just the right amount of bubble (if ya know what I mean!)! I'll never forget the way it swished back & forth walking up the stairs to her apartment. She was just absolutely gorgeous! Long black hair, beautiful face with these big brown eyes that NO MAN could've said no to. I still wasn't 100% sure if she was a man or a woman but I really didn't care at this point.
We got up to her apartment, which was small but comfy and clean. Living room, kitchen, bedroom & bathroom. We sat down on her leopard print sofa (how cool was that I thought) and we made a little nervous small talk. She asked if I'd like a glass of wine. As nervous and parched as I was, I woulda drank just about anything! We talked a little bit and started kissing. I thought I was gonna explode! These were the most amazing kisses I'd ever experienced, and at 18, I'd already been with quite a few women (being a musician and all). I ran my hand up her thigh...it was so soft and smooth yet sooooo firm.
Tiffany asked if I'd like to give her a massage. Hell yes I thought! She asked me to wait for a moment. She went into the bedroom and about a minute later called me to come in. She was laying there, face down, naked as the day she was born. And there was that beautiful black ass! I realized I was in uncharted territory for this white boy! I went over to the bed and she told me to take my clothes off as she wanted to feel my skin against hers as I gave her a massage. There was a bottle of lotion on the night table, so I squirted some into my hands and started massaging her back and ass and legs. She was so firm...almost muscular. After a few minutes she said she had a surprise for me and asked me to lay on my back and close my eyes...which I did. At this point, she could've got me to do just about anything!
Next thing I know, I feel her warm hands on my raging woody! A soft yet firm grip. Squeezing and gently tugging. WOW! was all I could think. White girls weren't too crazy about jacking a guy but Tiffany seemed like she was familiar with the territory! She then placed my cock in her mouth and started licking and kissing it. I thought I was going to explode! She started going down on me...faster & faster! I begged her to slow down bet she just shot me a sly little look like she knew what she was doing...and man, DID SHE EVER! She then laid on her side and grabbed my cock and pulled it towards that perfect black ass! She had what felt like vaseline on her hands and man did it feel good as she squeezed me. Without too much effort, she slid me into her ass and started thrusting against me! MAN! This was heaven! I started to feel her front as we fucked. Her tits seemed really small...almost non existent! As I felt that hot smooth brown skin, I work my way down. I figured it was definitely time to find out one way or another if I was fucking a man or a woman! Like I said, at this point, I really didn't care. It felt soooooo good!
All of a sudden, my hand came upon a huge and I mean HUGE penis! And this puppy was rock hard and greased for action! Oh shit! What have I got my self into??? It didn't matter....this all felt toooooo right! We were fucking on our sides, like champs! It was almost like a precision team in action! We just instinctively knew what each other wanted. As I was still kinda drunk, my hard on lasted for about 2 hours...all of which we spent fucking! Every position imaginable! I noticed while we were fucking doggy style that Tiffany was jacking herself off (aaaaaahhhhh! so that's why she was greased up! whew!) so I reached around and "lent a helping hand" so to speak. We fucked and fucked until we were both spent! Tiffany came about 3-4 times to my one big orgasm. I came so much and so hard that she was leaking like a sieve! When we were done, she had to change the sheets...which was the 1st time I got to see a full frontal view of Tiffany. Much to my surprise, I was still really turned on! She was really a he, with a thin yet muscular build, kinda like a swimmer. And that cock! Even soft, it had to be at least 7"! I was kinda glad that she wasn't pushing to pop my butt cherry but I have to admit that I was curious...and still am to this day!
We wound up laughing and joking and finally fell asleep. When I woke in the morning, there was a note saying to help myself to the shower, that coffee was brewing and that "T" would be back in a few...had to run an errand. I got up and took a shower and was still marveling over the previous night when I heard the apartment door open. I hurried and got dried and dressed to go see my beautiful Tiffany! I walked out to the living room and there was "Tony" (her real name)...dressed in his everyday "guy" clothing. It kinda brought it all home. Tony asked if I was surprised or disappointed and much to my surprise (and I think his too) I said that I wasn't and went on about how much I enjoyed myself and when could we do that again??? Tony said he'd call me (he never did) and that we'd have to do this again soon (we never did) but I knew that from that day on, my life would never be the same again...and here it is, 19 years later, and I still think of Tiffany from time to time. Tony too! Even as a guy I would've fucked him!
Copyright 2003 MCM