tagTransgender & CrossdressersA Love For All Time

A Love For All Time


Jamal Boyd is my name. I'm just one of the guys, as I like to say. I'm a young Black man living in the city of Boston. I'm a student at Suffolk University, studying Criminal Justice. I'm around six-foot-three, with light brown skin, fine features and a well-defined, muscular body. I'm a fine-looking man, if I dare say so. And I do dare. I'm like a younger version of Denzel, with a little Lee Thompson Young thrown in. Ok, now that you've got an idea what I look like, I'm going to let you know who you're dealing with.

I'm a native of Georgia and I came to Boston mostly to get away from my family. Talk about drama, right? Yeah, I come from a rather dysfunctional family. My dad Francisco is a firefighter from Atlanta who likes women of all races. My mother Ellen is a tall, square and loud Black woman. She talks a lot and shouts even more. Think Oprah without the wealth and power, but the same talent for whining. I've got a little sister named Lucy. She's a psychotic bitch with a mean streak the length of the Atlantic ocean. She hates my guts and tried to mess me many times, but I defended myself. I'm the kind of guy who doesn't take crap from anybody. I don't care if you're male or female, straight or gay, Black or white. You mess with me, you're going to get it. That's just how I do things. So, yeah, where was I? I came to Boston on an academic scholarship. I decided to become a police officer. It's the best job in the world if you ask me. I've seen the power that cops have and I wanted that power for myself. I don't want to be a low-ranking patrol officer. I can see myself as the captain of the Boston police department someday. Yeah, a police captain or even a chief of police. Black people are underrepresented in the field of law enforcement. This brother is representing!

When I came to Suffolk, the first thing I noticed was the females. There were a lot of pretty girls at the university. I saw all kinds. Tall, short, skinny, chubby, athletic or downright fat. Whatever you're into, they had it in this place. I was living in the dorms and my roommate was this guy named Michael Lander. Michael Lander was a tall, good-looking guy with Caramel-flavored skin and curly black hair. He was half Black and half Puerto Rican. A good-looking biracial brother. Michael Lander played football for Suffolk University. Like me, he came from Atlanta, Georgia. We had a lot in common. I loved the game of football but an injury during a high school game ended my career.

After football was over for me, I hit the books and became one of the best students at my high school. I maintained a GPA of four point two. That wasn't easy but I had the smarts to do it. I'm no slouch in the brains department. I'm probably the first former athlete in my school's history to become its valedictorian. There aren't that many male valedictorians anymore but I was one. Heck, I was the first Black male valedictorian the school had ever seen. Wasn't that nice? That's the way I am, I guess. I wasn't about to be outperformed by no man or woman. I'm supposed to be on top, no matter what. That's my motto. You don't have to like it, just don't get in my way.

Michael Lander and I became pals and we regularly hung out. He had a girlfriend named Jennifer Albright. She was a tall, slim girl with long blond hair and pale blue eyes. I guess Michael liked the white chicks. I don't have anything against white chicks but they don't often have what I like most in a female, and that's a really nice ass. Still, there are some exceptions. Michael Lander had a white girlfriend and that pissed off so many of the fine-looking Black girls at Suffolk University. Naturally, I decided to pick up the pieces. That's how I met Larissa. Larissa was this girl who had a thing for Michael but gave up on him when he picked Jennifer to be his lady. Personally, I think Michael is dumb for picking Jennifer over all of them fine-looking Black and Hispanic girls but hey, what can I say? Michael Lander, Black athlete extraordinaire had fallen in love with Jennifer Albright, a female softball player who happened to be the whitest person on campus. Can't stop love, I guess.

Larissa was at a party where the football players were having some fun after winning twenty of the games they played so far against teams from around the state. I immediately noticed Larissa. It would have been hard not to. She was a chocolate-skinned girl with long braided black hair and slightly angular features. At around five-foot-ten, she was curvy in all the right places, especially the rear. Larissa had what the boys from the hood called a "bubble butt". The kind you can't help noticing a mile away. I noticed, and approached her.

Larissa was standing in the living room, talking to some of her girlfriends. Every female I know always goes out surrounded by her pals. They travel in packs, for support I guess. I'm not a pack animal. I like flying solo, for the most part. Sometimes, I hang out with the guys but their games has to be tight, just like mine. By game, I mean that the dude has to be at the same level as me. He can't be an ugly dude. He also can't be broke all the time or even worse, stuck with a seriously ugly girlfriend.

I started talking to Larissa, and learned a little more about her. Larissa was eighteen years old and wanted to become a journalist someday. She was also a native of Texas. Black girls from the countryside aren't usually my cup of tea but I make exceptions when they looked like Larissa. She asked me plenty of questions about myself, and I told her what I felt was necessary to satisfy her curiosity. I'm a firm believer in never telling anyone more than they need to know. It's an ancient rule of mine and it has never failed me. As the night went on, we started dancing. Larissa had some good moves. Her sexy body followed mine nicely as we danced to the beat of an Eminem song. When she turned around and started bumping her sexy ass against me, I started to really feel this girl. If she wanted me excited, well, it was working. We danced the night away. There were plenty of other couples dancing at the party but none of them looked half as good as we did. I have to hand it to Larissa. The girl had it going on.

As the night went on, it became clear to me that Larissa was really feeling me. I'm an equal-opportunity lover if there ever was one. I'm freaky like that. I'll do anyone if I get horny enough. A hot chick or a good-looking dude, it's all cool with me. We went upstairs. Some people looked at us. A dude smiled at me. I winked at him. Yeah, I was going to get some. We went into a room and started making out. Larissa put her arms around me, and then it was on. I really wanted her and I could tell that she wanted me just as badly. We kissed and began to slowly undress each other. Pretty soon, we were both naked as the day we were born. Larissa had a really sexy body. The girl had a bit more flesh on her than I previously thought but she still looked sexy. I'm kind of fond of Big Beautiful Women, to tell you the truth. She wasn't far from being one. I looked at her, and grew quite aroused. She had a set of large, firm-looking breasts and a pretty face that lit up when she saw my naked masculine form.

I touched that sexy ass of hers and she purred. I made her lie on the bed and spread her legs. I looked at her pussy. She didn't shave but I didn't care. I'm freaky like that. I started to lick her pussy and finger her clit. She closed her eyes and enjoyed what I was doing to her. As I licked and probed her, she began to moan softly. I could tell that she liked it by the way she was responding. I made her cum that night, and she screamed so loud that I'm pretty sure everyone in the frat house heard her. But I didn't care. When I was done, she lay there, looking at me with wide eyes. Yeah, I could tell that she was surprised by my oral skills. I'm one of the best out there, if I do say so. I stood up, and gestured to my dick. I was hard and saw her eyes grow even wider when she saw it. I'm a rather well-endowed man. Eight and a half inches long and quite thick. I'm an uncircumcised brother with a big one. I watched as she took me in her mouth and began to suck my cock. I pumped it into her mouth very slowly, letting her get used to its girth. Larissa had skills. She flicked her tongue over my cock head and licked my balls. I was almost shaking with pleasure and hard as a rock. I was ready for the main event.

When she had gotten me as hard as I could possibly get, Larissa told me to give her the treatment. The treatment is what every willing and attractive young lady who comes to bed with me gets. I was ready to enter her in the missionary position but she had something different in mind. She simply got up and went back to her clothes and bag, which lay in a heap on the floor. I thought she had changed her mind. It wouldn't be the first time that I took a hot girl to bed and she changed her mind. I didn't like it but I accepted it. Larissa came back, with a bottle of hand lotion in hand. My eyebrows were raised but when she winked at me, I knew what she had in mind. She took some of the lotion and applied it between her sexy cheeks. Then, she got on all fours, and spread her cheeks, exposing her brown little hole. I smiled at her. I couldn't believe my luck. I've had anal sex before but I've never had a girl volunteer for it. Damn, this girl was something else.

As she handed me the bottle of lotion, I put on the condom I kept in my wallet and then applied some lotion on my condom-covered cock. I was ready and so was she. I positioned myself behind her and pressed my cock against her rear entry. She urged me to continued. Slowly, I slid inside her. There's something about anally penetrating a woman that really gets me. No matter how many times I've done it. Not many girls like it but I thank Heavens for those who do. I was gentle as I slid into her. Her ass was tight but yielding, thanks to the lubrication. I placed my hands upon her hips and thrust into her. Slowly but surely, I fed her rear five of my eight-and-something inches. She took it, and loved it. I could tell, judging by the way she backed up against me and urged me to fuck her harder. I did. Her anal canal felt warm and tight around my cock, and gripped me like steel. It wasn't long before I came. Slowly, I pulled out of her. We lay on the bed, both of our bodies covered with sweat. Larissa smiled at me and gave me a kiss on the lips. I grinned and looked at the ceiling. I had finally found my fuck buddy at Suffolk University.

After that memorable night, Larissa and I became regular fuck buddies. The girl was very hot and our sex life was vigorous and spicy. She had it going on! Larissa had another guy on the side, a swimmer named Keith Brown. The only Black male on the swim team. I didn't mind that Larissa had other guys. I always used condoms with her and I wasn't interested in a relationship at the moment. I was a young Black man in college. The last thing I needed was a girlfriend who was a jealous hussy and made me feel trapped or worse, smothered. I continued my studies. I had to maintain my grades otherwise I could kiss my scholarship goodbye. Nobody can last long without money in the city, so I found myself a job. I worked as a security guard inside one of the biggest shopping centers in the city. Prudential. It's a really cool place where all the rich people do their shopping. What I like about it is that regular people go there often too. So, yeah, I was a security guard and my manager was this woman named Nicole Taylor. Nicole Taylor was a tall, good-looking Latin woman with short red hair and pale blue eyes. A very attractive broad, if you ask me. What I liked about her is the fact that she had a wicked sense of humor, and a great ass.

For the most part, I enjoyed my job. Eighteen bucks per hour for doing basically nothing sounds cool to me. The scholarship paid for room and board as well as tuition for me, so I was cool. On the weekends, I had plenty of money to spend. One time, I ran into Nicole Taylor at a club. She was there with her girlfriends. When she saw me, she came over to talk. She was looking really good in a low-cut dress. I noticed her great legs and curvy form. Yeah, she definitely had my attention. She asked me to dance and of course, I agreed. We started dancing, and later bumping and grinding on the dance floor. The way Nicole was moving with me, I could tell that she was feeling. When she asked me to come to a back room with her, I didn't resist. We went inside, and that's when I got the surprise of a lifetime. Nicole was kissing me and I started feeling her up. That's when I noticed something that was definitely out of place. Something was poking against her underwear when I tried to give her a feel.

What in hell? Nicole stared at me with wide eyes. I demanded an explanation. She told me that she was a transsexual. I looked at her. She was so good-looking. Usually, I can spot transsexuals because something of their former nature remains with them even after surgeries but with her, I couldn't tell. Nicole Taylor looked like a cross between Anna Kournikova and Jennifer Garner. A tall, sexy woman. The last person you would ever suspect of being a transsexual. Yet she was. I was surprised. She asked me if what she was disgusted her. I scratched my head. I'm not a bigot, alright. Even though I hate labels, I consider myself to be bisexual. I'm the last person who should reject someone because of their sexual identity.

I shook my head and told her that I was cool with her. I also asked her why she thought she had to lie to me. She told me that had felt attracted to me ever since I came into her office for an interview. Heck, that's the reason why she hired me in the first place. I was rather flattered. She shook my hand, formulated an apology and headed for the door. I looked at Nicole's hot butt while she walked away. Her butt looked fine enough to make Jennifer Lopez jealous. I couldn't believe what I was considering but there was no way that I was going to pass up on an ass like that. I hurried after her and she turned around, looking at me. I looked into her face. She was so beautiful. Unless she had told me, I never would have guessed what she was. And I felt attracted to her. Powerfully so. Guess what happened next?

Nicole Taylor took me home. She lived in a nice apartment in the Back Bay. A really nice place. I found out more about her. We sat on her couch and sipped some wine. Nicole Taylor was born Nicolas Taylor. Nicolas Taylor was once the star of the swim team. Nicolas had never felt right in his own body. He always felt like he was truly a woman but acted in a macho way around people so they wouldn't suspect. He was tall and slender, good-looking and attracted lots of women. For some time, Nicolas had both male and female lovers. He thought he was only bisexual, but began to dabble into cross-dressing. Nicolas eventually got so confused that for his own sanity, he began to see a shrink. The psychiatrist he saw told him that he was a girl in a man's body. A mental health professional confirmed what Nicolas had known his whole life. He decided to finally be himself.

He worked hard in college and graduated with a degree in Business Management. He began working for a Bank and worked his way up the corporate ladder. Eventually, he made enough money to pay for gender-reassignment surgery. Nicolas Taylor was transformed into Nicole Taylor. Nicole Taylor, the tall, big-bottomed, large-breasted, sexy woman who sat next to me. Nicole told me that she left the business world and began working in security. She founded this security agency that catered almost exclusively to the needs of gay, lesbian, bisexual and transsexual people. A lot of wealthy GLBT people didn't exactly feel safe at work or at home, since there were so many homophobes out there. They were willing to pay top dollar for great security. Nicole Taylor wasn't only the founder of Taylor Security Agency or TSA. She was also the first transsexual CEO in America. Featured in the book of records and also on the cover of the Advocate. I was impressed. Nicole was a living legend. One of the GLBT community's big success stories. I was curious as to why the CEO of a growing company would try micro-managing it, but Nicole told me that she loved keeping tabs on her workers. Smart plan, if you ask me. I was really impressed with her.

I told her a bit about myself. For some reason, I felt really comfortable talking to her. I told her my story. The story of a young Black man who went to a small high school in Georgia. I was a football player and academic super star whose athletic career got cut short. I devoted myself to become one of the greatest academic luminaries in my town's school system. I was the first Black male valedictorian the school had ever seen. At the same time that I was dealing with all that, I also had an internal struggle that nobody knew anything about. I had to deal with my emerging sexual feelings for members of both sexes. Now, in Boston, there are so many gays and lesbians that it may seem the norm to see a same-sex couple kissing and holding hands. It's not like that in Georgia. A man seen holding hands with another man in Atlanta will get ridiculed or even physically assaulted by virtually anyone they encounter. Homophobia runs rampant down there, and the Black community is a lot more homophobic than any other. That's why I kept my business to myself. I chose to go to school in Boston because Massachusetts was hundreds of miles from Georgia, so I would be free to live however I wanted there. Now, on the surface, I appeared heterosexual and led a heterosexual lifestyle but beneath it all, I was a bisexual Black man who often longed to be with a member of his own gender. I wasn't about to take chances with my college career, so coming out was not an option.

Nicole Taylor calmly listened to me while I told her my story. I told her of the time I developed a crush on my friend Anthony Smith. Anthony was a tall, good-looking brother with jet-black skin and a shaved head. He looked like an ebony god and I almost salivated at the sight of him. Anthony Smith was also a five-time state champion in wrestling. He was respected by all the boys and desired by nearly all the girls I went to high school with. He was a good-looking, smart young brother at the top of his game. I was his buddy and I secretly desired him. I didn't think anything would ever come out of it because Anthony had a girlfriend named Rachel Jenkins. Rachel Jenkins was a tall, good-looking light-skinned Black female. The kind who made heads turn anywhere she went. Yet, somehow, I got to be with the guy I loved, even if it was only for a little while.

One day, I saw Anthony in the boy's locker room after gym class. It was in late April, just a couple of months before the senior class graduation. I had recently turned eighteen and so had he. There he was, a spectacular Black athlete. So handsome that he made me feel weak in the knees. We were the only ones in the locker room. Everyone else had left to go home. I looked at him. I couldn't help it. He was simply gorgeous. He turned around, looked at me and smiled. I grinned and waved. He walked toward me, and almost stilled my heart with the words that came out of his mouth. He told me that he had seen me checking him out and knew that I was at least bisexual. I was shocked. Anthony had caught me checking him out? What was I to say? Deny it? He already knew. Would he tell people? We still had a month and a half of school left. I really didn't want people around school calling me names or harassing me. Anthony smiled and said that he wasn't going to bust me. I asked him what he was going to do. He looked me in the eye and told me that he was going to give me what I always wanted. Then, he kissed me. In that moment, I left the straight world behind.

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