Have you ever been so infatuated with someone that you would do almost anything for them? Not in love with the person but a deep sexual, lustful infatuation? The infatuation is so strong that you would act uncharacteristically with that person? You would allow that person to manipulate you, take advantage of you, and do whatever that person told you to do? I had that type of infatuation with someone once and it lasted for about eight months before I got over it.
My name is Bella and I am a thirty-four-year-old female transgender female. I started my transition when I was eighteen. This story is about the time a couple of years ago when I had just such a sexual infatuation with an eighteen-year-old boy named Derrick.
To put our relationship in perspective, Derrick made me his willing bitch for almost a year and I enjoyed it immensely. Our relationship lasted from the spring of 2022 until he went to college in the fall of 2022. We even hooked up a few times when he would come home from school until I finally got over my seemingly uncontrollable lust for him.
I am not going to go into full detail about my past or my transition, but some past I need to tell because it pertains to how I got involved with Derrick. When I was nineteen, I left home and moved to Miami to live with a friend who was also transgender. I didn’t run away from home, I just was young and trying to figure things out and what I wanted to do with my life.
My roommate was an escort and after working as a waitress and not making enough to pay rent, bills, and other expenses, I asked her to set me up with the agency she worked for. I worked as a transgender escort to pay for my breast augmentation surgery, other transition expenses, and everyday expenses.
My favorite clients I had when I was an escort were the ones who wanted the girlfriend experience and I enjoyed providing just that, regardless of how they looked. Trust me; it was not like in the movies or TV where the clients are handsome and rich. I never had a handsome client, but when I was with them I made them feel and treated them like they were princes. It helped with tips afterwards or they would request more time with me because I made them feel so good.
Other clients would just pay for an hour, have me suck their cocks for a while and fuck me hard and rough and tell me to leave when they were done. Those weren’t too bad because they were normally done before the hour was up, but still had to pay for the entire hour. The worst times were when the men wanted me to fuck them or the time I had an appointment with a couple.
I am a bottom type girl and don’t enjoy topping men and the thought of it does not turn me on. I could not even get an erection when I had that request to do so the first time. The next time I learned to take a Viagra before I met with a client that had that fetish.
The couple was the same because I was expected to fuck the wife also. Just like topping a man, women do not turn me on sexually. The Viagra worked well in that situation. She wanted me to go down on her pussy, but I had to draw the line somewhere. The mere thought of going down on a woman’s pussy makes me ill.
During the same time, I did four different porn scenes while in Miami.
The first porn scene I did was one of those casting couch scenes. The second was the so-called reality porn, but they were not reality and were set up. The type of porn where two men are going around with a video camera and hooking up with a girl and then taking them back to their apartment. While in the apartment, they find out the girl is transgender and she convinces the one man to fuck her.
The third was part of a series of transgender babysitter porn where I played the babysitter who seduces the father. The last was a porn scene with no plot where I was fucked by a black man. At the time I did the scene, he was popular in the industry for the size of his cock.
He was cock was so large that when he was fucking me I had to call out for a break several times because of his size, how rough he was fucking me, and because of how long he fucked me. They edited the scene to make it look like it was shot in one take.
The edited scene was over forty-five minutes long but with the breaks I needed from getting fucked by such a huge cock the recording of the scene was well over an hour. After the man shot his cum into my ass, my insides felt like mush and my asshole felt as if it would never recover. I did have three orgasms during the shoot and it was a great fuck. Of the four porn scenes I did that one was the most pleasurable sexually.
What I did as an escort and the short stint in the porn industry does not reflect my personal life. As the saying goes, it was not personal, only business. I am not a prude sexually and enjoy my kinks and fetishes. I do enjoy getting a nice hard fuck on occasion, my hair pulled, and my butt smacked while getting fucked. I also enjoy dressing up in lingerie for a man I am seeing or other sexy outfits for him.
That being said I don’t just jump into bed with someone as soon as I meet them. I have had a few one-night stands or dated a man for a few months just for sex, but normally that is not who I am. I enjoy romance, intimacy, showing and receiving affection, kissing, and cuddling. I believe in love and that one day I will find it, but I am not going to be celibate before I do. I like sex a great deal.
I have dated men who I wanted to have something more long-term with, but they didn’t. They just dated me for a while to fulfill their “transgender fetish” and when satisfied until it rose in them again, they stopped dating me. I have only had one serious relationship since I started my transition.
There were several things about my infatuation with Derrick that I could not make sense of. One of course was his age. I did not chase after young boys and preferred men even when I was younger. I had not had sex with an eighteen-year-old boy since I was sixteen. Then there were his looks.
I consider myself an attractive woman and have been told I was many times. I am feminine, have a nice body, and am pretty. I don’t consider myself a narcissist, but I can be somewhat vain about my looks. I am not tall, standing only five foot six inches, my breasts after my surgery are thirty-four C and I have long dark brown hair. I have always dated masculine, attractive men. Derrick was not that.
While not feminine in looks, personality, or mannerisms, Derrick was a nerd and looked like one. He was tall, skinny, not attractive, and had a mild case of acne on his forehead that never cleared up while we were together. It was not at the point where it was gross-looking, but it was noticeable. He looked like the classic nerd from movies and TV minus the nerd glasses.
The boy was exceptionally intelligent and had a love and fascination with science and anything electronic, robotic, and computers. His intelligence made him a very arrogant young man who liked to correct people when they were wrong just to embarrass them.
By the time I started my affair with the boy, he had written a Mod for a particular computer game he played. The Mod became so popular for the players of the game that the company who created the game paid Derrick around thirty thousand dollars for the Mod. He put the money aside for the college he was going to attend after he graduated high school. Derrick had been accepted to MIT. Yes that MIT, The Massachusetts Institute of Technology in Cambridge, MA. The boy did have a reason to be an arrogant asshole.
As our affair progressed, there were the things I not only allowed him to do to me and I did for him but highly enjoyed doing them and made my suggestions of ways we could do kinky things.
I am not a submissive woman for the most part and not at all subservient to the men I date. Yes, I have enjoyed submissive activities such as being tied up and fucked and played with and having sex toys used on me, but I never considered myself a submissive person sexually. I certainly am not submissive or subservient in my non-sexual life. With Derrick, I was both sexually submissive and subservient to him non-sexually.
I am an affectionate and passionate woman and I love sex and being sensual, but when I don’t want to have sex, no means no. With Derrick, however, I could never say no to him and I could not keep my hands off the boy. I constantly wanted his cock in my mouth, to taste his cum, and for him to fuck me. I could never resist him even though I often tried at the beginning of our affair.
I still don’t understand why I was like that with him and not like that with other men I have dated or had sex with. Well, at least where I was not getting paid to have sex with them. When I was an escort and the men paid me to be submissive, I was.
When we first started having sex, Derrick was a virgin, which I was not surprised by. I soon learned that he must have gotten his sexual education from watching certain porn genres. The type where the men were rough and dominant and controlling with the women they fucked. The unbelievable type of porn where the woman is telling the man no, but as soon as she sees his cock she can’t control her sexual desires.
Derrick liked to plan things out before he acted on them and he did so with the thongs he did to me and had me do with him. I could imagine him lying in his bed before he went to sleep thinking of what he would do to me or have me do the next time we were together. He was also a bully.
Derrick didn’t physically bully people, but did so with his intelligence and his words. He bullied me and the nerd friends he had. I suspect he did so because he was bullied at school and not being able to physically bully people. He used words and brains to bully people he could. Derrick seemed to be the leader of his small group of nerd friends he hung out with.
Derrick could be cruel and a little sadistic and enjoyed humiliating people with his intelligence and also, as I found out sexually, as well. He had other fetishes and kinks, some I had done before and others I had not. I not only helped him satisfy them, but enjoyed helping him satisfy them.
My infatuation for the boy was so strong that not only did I tolerate him to treat me in such ways, but going against my personality and character, I thoroughly enjoyed him treating me that way and got off on it. He treated me in a way I had never let a man treat me unless being paid for it when I was younger. I came to get a great deal of pleasure from it that after my affair with Derrick ended, I not only allowed other men I dated to do some things to me Derrick had done, but I encouraged it and suggested it.
It even got to where when Derrick would not see me for a week or even longer I got scared he was getting bored with me and would send him text messages begging for him to come over and see me. I would promise him he could do anything he wanted to me if he would just come over and at least let me give him a blowjob and taste his cum.
The boy quickly started to consume my thoughts, and he was all I could think about. I would spend money on him; buy any sexy outfits he wanted me to buy to wear for him, and any type of sex toy he wanted to use on me I purchased.
I even took the boy on three out-of-town trips for a few days and paid for everything. On one three-night and four-day trip, we went to the mountains, where I rented an isolated cabin. Derrick bought a friend with us. The two boys fucked me almost constantly, played with me, had me dress certain ways for them, and acted out kinky sexual games with them.
I enjoyed our trips, not just for the sex, but because on the trips we didn’t have to hide our relationship and could go out in public together. We would go out to eat, walk along the beach, hold hands, and show other public displays of affection.
I knew Derrick had a transgender fetish, and he watched transgender porn. I knew that from how our sexual trysts began. He liked fucking my ass pussy, as he liked to call my butthole. The eighteen-year-old boy treated me like his personal porn star and whore, and I allowed him to because I had become so infatuated with him.
I was thirty-two when I started my sexual relationship with Derrick. My past as an escort and working in porn was way behind me. I had graduated college and was working as a supervisor in the IT department for a large well-known company. I mostly worked at home since Covid and most of our meetings were done on video calls.
I had transferred to another city in another state when I took the supervisor job and that ended the relationship I had been in for almost two years. We tried to make it work, but neither of us was good at the long-distance thing so we agreed to end our relationship; him more than I was. I was sad about it but I could not pass up an opportunity to advance my career.
After living in the new city for almost a year in an apartment, I decided to buy a house. I was making enough money and could financially afford my first house. I did my research and bought a three-bedroom and two-bath home in a nice middle class neighborhood in the suburb of the city. The main selling point to the house for me was it had a nice pool in the back; the only home in the neighborhood that had a pool. It was eleven years old when I bought it but in great condition.
The house I bought was in a neighborhood that was originally developed to be an upscale, self-sufficient, gated community. There were plans to have a grocery store chain to build a store in the community for the residents, a convenience store, and a gas station. They planned to have tennis courts, hiking trails, and other amenities for the homeowners.
That all fell through before a single home was built. Investors pulled out and one developer embezzled millions and left the country. Another developer purchased the land and built a nice middle class community. There was still a clubhouse, we had a homeowner association, and the community was gated, but the gate was never closed. They never did build the tennis courts or the swimming pool they planned.
Being a new homeowner and wanting to embrace it I became active in the community. I went to the homeowner association meetings, mingled with other homeowners, went to neighborhood parties at the clubhouse, and met some of my neighbors. I was even considering running for a position on the association board.
My neighbors know I am transgender. I don’t go around advertising it and I am not some LBGTQ+ activist and don’t fly a rainbow flag from my house, but I don’t hide the fact I am transgender either. If asked, which very few people do, I tell them I am. When at a bar or club and a man is flirting with me, I tell them I am; most of the time they lose interest in me after that.
The reason my neighbors knew I was transgender is that my real estate agent has a big mouth. She told a few people who then told a few people, etc. No one seemed to care and everyone was friendly with me. I will confess that I did get some not-so-innocent looks from some of the husbands who seemed to like staring at my ass and breasts.
Some of the husbands harmlessly flirted with me when I would see them in the gym at the clubhouse and their wives were not around. Based on some looks they gave me when they didn’t think I could see them, they liked me in my yoga pants and sports top. Sometimes I even saw them looking at my crotch, hoping to get a peak.
I have an average size penis but when not erect or semi-erect, I am what people call a “grower not a shower”. It looks like one of the nude statues of men from Ancient Greece. I was flattered by their looks and flirtations. Of course, I would never act on it. It was not because they were married. I had been with married men before, but because I knew and liked most of their wives.
How did my affair with the eighteen-year-old boy start? It started with blackmail. I soon embraced it even if I did often use being blackmailed as an excuse for letting Derrick fuck me in the beginning.
I admit, I sometimes would refuse to do what Derrick asked so he would bring up the reason for the blackmail again to make me do things for him, and it turned me on. I started to get off on the thought of being blackmailed.
It was a Saturday afternoon in early spring and I was excited to use my pool for the first time since I moved into my house. I put on a rather skimpy bikini with thong bottoms. I liked to sunbathe and get an all-over nice tan and I would remove both the top and bottom as I lay out in the sun. Because of my natural skin complexion, I rarely sunburned unless I was out in the sun for hours at a time. I knew the limit of how long I could sunbathe before I started to get sunburned.
I was not worried about anyone seeing me since I had a tall privacy fence in the back and there were no two-story homes next to my house. The only way someone could see me was if they stood on a ladder and looked over the fence.
Not planning on anyone seeing me that day, I didn’t bother with makeup and didn’t style my hair long brown hair. I just put it in a ponytail. My hair is naturally curly and frizzy, so I normally straighten it if I am going out or having company.
Wearing my thong bikini and a sarong style wrap around my waist and carrying my towel, sun tanning lotion, phone, earbuds, and my Kindle, the latest book in a series I was reading, I went outside to the pool. I was out for about twenty minutes when I removed my bikini, listening to some music on my phone, and reading the next book in a series of erotic fiction on my Kindle.
It was the fourth book in the series about a four-hundred-year-old, beautiful nymphomaniac, hermaphrodite vampire, and her masculine male human lover. It was about the adventures they get into while trying to stay a step ahead of a group of vampire hunters. The storyline was not that good and was predictable, but the erotic scenes were great and detailed.
I was reading a particular scene where the vampire and her mortal lover were having a foursome. It was with a powerful male vampire and his male fairy servant, a fairy as in supernatural fairy, not a feminine male gay fairy; the cost of protection they needed from the vampire. Julian, the hermaphrodite vampire, was getting her ass fucked by the older, more powerful vampire while his fairy servant was fucking her pussy. Her lover was standing on the bed and she was sucking his cock. She was having a wonderful time.
I was running my hand sensually up and down my hard cock. I was not jerking off but enjoying the sensation of my fingers gently running up and down my average-sized penis. I had not had sex since I moved into my new house just over eight months before that day.
Before then I was having sex occasionally with a divorced, forty-two-year-old man who lived in the same apartment building I did. We met in the building’s gym. We didn’t go out on dates and he would fuck me about once or twice a month when he felt the need to satisfy his fetish of having sex with a transsexual. I would have preferred more and even dated him, but as they say, beggars can’t be choosers and I took what I could get to satisfy my sexual desires.
I masturbated, of course, and fucked my ass with a dildo on most occasions when I did, but I sure missed the real thing. I missed the touch of a man’s hands on my body, kissing him, sucking his cock, tasting his cum, lying next to him and cuddling after we fucked, and the overall human contact of a lover. I enjoy being romantic and affectionate with my lover.
After I finished reading the erotic passage in the book and touching myself, I was sexually aroused and was tempted to use my coconut-scented suntan lotion and jerk off. I didn’t because I was suddenly startled when I heard a loud knocking on the gate of my privacy fence. I removed my headphones and looked over at the gate and heard and saw someone trying to open the locked latch.
“Fuck,” I said aloud. “Just a moment,” I called to the person trying to open the gate.
I got up from the poolside lounge chair, put back on my bikini, wrapped the sarong around my waist, looked down to make sure my erection was not noticeable, and walked to the gate. I now wished I had worn a different bikini. The sarong covered my bottom, but the bikini top was revealing and didn’t cover much. I opened the gate and Derrick was standing there with a grin on his face.
“I knocked on the front door but no one answered,” he told me. “I came by to ask if I could use the pool. You told my mom I could.”
I had officially met the boy once when his mother introduced us. Derrick’s mother was the president of the homeowner association and she introduced us at one meeting. Derrick attended most of the meetings with his mother, making me think he was a momma’s boy, but besides the time I was introduced to him, he had never spoken a word to me. Trying to get into her good graces, I did tell her that she and her husband and her son could use my pool provided they ask me first.
“Today’s not a good day,” I told Derrick as he was staring at my chest. “I was just about to go in and get dressed and run some errands,” I lied.
“Sure it is. It’s a nice day,” he told me.
Derrick then walked past me and into my backyard. I sighed and was annoyed by his audacity. It didn’t dawn on me at the time but I thought about it later that day. I don’t think he came by to swim by the way he was dressed. Derrick was wearing a pair of white basketball athletic shorts, not a swimsuit. The shorts came down past his knees. He was wearing a tee shirt and his socks were white calf-high socks.
“Derrick, I think you should leave,” I told him as I followed him to the pool. “I told you I had things to do today.”
The boy ignored me and walked to the lounge chairs and sat down in the one I was previously using. He pulled his phone out of his front pocket and started using it. He looked up at me and gave me a mischievous grin.
“I want to show you something, Bella. Why don’t you sit down,” he told me. He patted the area on the chair next to him.
“What is it?” I asked.
Derrick chuckled. “I have to show you and you may want to sit down for this,” the boy told me.
I shrugged and sat down as far as I could from him. He moved closer to me. Derrick held up his phone, and I looked at it. He had opened to a video, and he used his finger to press the play option. As soon as the video started, I blushed. I knew what it was.
The video started and on his phone screen was a twenty-year-old me standing next to a bed and wearing red lacy panties and a matching bra. It was the porn scene I did with the black man. I did some modeling moves and pulled aside my bra to show my then-small breasts. It was before I had my implants and my breasts were small, natural breasts from the hormones I was taking.
I did some more poses and then turned around and bent over slightly to show my butt. I pulled aside my panties to show my ass more, turned back around, and then pulled aside my panties to show my erect penis. I then sat down on the bed as the black man came into the shot.
“I don’t want to see your porn,” I told the boy and tried to stand up, but Derrick grabbed my arm and pulled me back down.
“My porn? This is your porn, Bella. You’re the one in the video,” he told me.
“That’s not me,” I lied.
Derrick laughed at me. “Yes, it is.”
The video was over ten years old and I was twenty at the time. I was thinner and my butt was skinnier and I did not have breast implants then. My boobs were small from the hormones I was taking. Still, there was no way I could deny it was me in the video, even though I tried.
“How did you get this?” I asked as the video continued to play.
“I saw it about two weeks ago when I was on my computer looking at porn,” Derrick answered. “Imagine my surprise when I came across this one.”
I was surprised he came across it as well. The video was shot over ten years ago and I used a different name in the porn videos I made and when I was an escort. It had to be a one-in-a-million chance someone I knew would come across it.
“Why are you showing me this?” I asked.
“I don’t know how you fit that big black cock in your mouth and then in your ass,” Derrick said as he ignored my question.
I looked back at his phone and in the video; I was now down on my knees sucking the man’s cock. He was holding my head still and fucking my face and I was gagging and choking on it and spit was pouring out of my mouth.
“You can stop it now?” I told the boy.
“I like this part,” Derrick told me and used his thumb to fast-forward the video.
I again looked at his phone and Derrick was now showing the part of the video where I was still on my knees, but my porn partner had turned around and was bent over. I had my hands on his black butt cheeks to spread his butt apart and was licking, rimming, and then putting my tongue into his asshole.
“Fuck, you sure are a nasty whore,” Derrick commented as he watched the scene.
I again didn’t say anything and turned my head. I didn’t need to watch it play out on the video. I knew what was next. I licked my partner’s asshole for a while as I used my hand to stroke his large black cock. After several moments, we got on the bed and I started riding the man’s penis in a reverse cowgirl position. My porn partner was jerking my cock as I was moaning loudly and telling him how big he was and how deep inside my ass he was.
“Are you always that loud when you get fucked or was it just an act for the video or was it because he was so big?” Derrick asked.
“That’s enough, Derrick,” I again ignored his question.
The truth is, I am that loud when I get fucked, even if my partner in the video had not been so big. I was not acting in the video and highly enjoyed getting fucked by my partner’s big black cock.
“Wait, here comes the good part,” he said.
As I was riding my partner, I started to orgasm. Cum exploded from my cock as the man jerked me off. I was making loud, whimpering moans as I orgasmed. The man then brought his hand to my face, and I licked the cum off of his fingers. When I was done, he moved my body to lay me on my back and started fucking me again. What was not shown and edited was after I had an orgasm, I had asked to take a break. They edited that part out.
“Why are you showing me this?” I asked the boy as I crossed my legs to hide my erection.
Before the boy knocked on my gate, I was aroused and hard, but when he invited himself into my backyard I was annoyed and no longer aroused. Now, watching my younger self on the video, I became aroused and erect again.
“We will get to that, but I want to show you my favorite part,” he told me.
Derrick again fast-forward the video to near the end. I was on my back, my partner was on top of me, had my legs pushed up over my head, and was fucking me hard and brutally. I was moaning and screaming out louder from the pleasure of getting fucked so hard by such an enormous cock. My partner fucked me like that for a long time before he shot his cum into my ass and pulled out of me.
“Damn, that black cock sure stretched that ass-pussy out, didn’t it?” Derrick asked and chuckled. “You could fit a football up your ass after he got done with it. I like seeing his cum run out of you.”
I looked down at the video and so myself panting for air. I was holding my legs up as my partner stepped out of the view of the camera. The camera did a closeup and my butthole had gaped wide and my porn partner’s cum was running out of my asshole. I was told to stay in that position for the camera to capture it.
“Why are you showing me this?” I repeated my earlier question.
Derrick chuckled. “It’s called blackmail, Bella,” he told me bluntly.
I laughed at that. “You think I am ashamed of that?” I asked the boy.
While I didn’t want people to know what I did when I was younger, especially my family, I was not ashamed of it. I was young, and I did what I did and can’t take it back, so there was no point in being ashamed of it.
“Maybe you aren’t or maybe you are lying, but do you want the entire neighborhood and the homeowner’s association to know you’re a porn star and a sexual deviant?” Derrick replied.
“I’m not a porn star and not a sexual deviant. I was younger, and that was the only scene I did,” I lied.
“Maybe you’re not, but they won’t see it that way and you want to be on the homeowner’s association board. Do you think they would let you after they saw this?” Derrick explained. “You think everyone is so accepting that you are transgender, but they are not. Some are like my mom and dad, but there are a lot of others who aren’t. They just act like it because they want to be seen as open-minded, but they whisper behind your back and call you a pervert and other things.”
“I…I don’t believe you,” I told the boy. My confidence was starting to decline as Derrick told me these things, and I knew deep down he was not lying.
“Does not matter if you believe them or not,” he continued. “I am telling you what I know and have heard after you leave the meetings or people tell my mom and dad and what other people say about you. They would most likely approve you to be a member of the association because they are afraid not to. They would be scared you would make a big deal out of it and say it’s because you are transgender. But if they see this video, they have an excuse not to only reject you but also ostracize you for being a pervert.”
I swallowed hard as Derrick closed the video on his phone and opened up another video. As much as I wanted not to believe him, I knew he was right.
“Then if I show them this video also,” he told me with a grin. “You really should fix that hole in your fence if you are going to keep doing this in your backyard.”
I didn’t know I had a hole in my fence. I looked down at his phone and saw myself just moments before Derrick knocked on my gate. I was naked, reading the book on my Kindle, and slowly stroking my erect penis.
“What do you want, Derrick?” I asked.
The boy gave me a smile like a villain from a movie whose master plot to take over the world was coming to fruition.
“I think you know what I want,” he told me.
I laughed this time. “That is not going to happen,” I assured him.
“I think it is. I think before we are done, you are going to do whatever I tell you,” he countered.
“I don’t think so. I think you are bluffing, anyway. You show those videos and people, including your parents, will know you’re just a little pervert who likes transsexual porn,” I told him with confidence. “How would your friends like to find that out?”
Derrick chuckled again. “You think they would know I showed them. I made a dummy email account just for that purpose,” he told me.
Derrick again went to his phone and pulled up an email account, typed the email address to the homeowner’s association in the “To” field. I was calling his bluff and waited to see what he would do next. Derrick didn’t taunt me or try to bluff me before he was going to send the email. I now knew he was not bluffing.
“Wait, wait, wait,” I told him before he could press the send option. Derrick looked at me and smiled again. “What…I have some money,” I told him.
The boy shook his head. “I don’t need money. I need something else,” he told me.
I bit my lower lip and thought things over for a moment. I didn’t want people to see those videos, and I knew he was not bluffing. Derrick was right, it would not only humiliate me if people saw them, but they would think I was a sexual deviant and pervert. I knew I already had one strike against me. While people outwardly accepted I was transgender, I lived in a pretty conservative neighborhood.
“I’ll…I’ll give you a blowjob,” I told the boy. “But that’s all.”
Derrick chuckled again and stood up and faced me. He stood about a foot from my face and I looked down at his crotch. I could see he had an erection before I turned my head.
“Yes, you are going to do that, but you are going to do something else for me first,” he told me.
I looked up at him. “What?”
“I want to see your tits and your girl cock,” the boy told me.
I took a deep breath and nodded. I removed my bikini top and then hesitated. I didn’t want to remove my bottoms because my penis was erect and I didn’t want the boy to see me with an erection. I didn’t want him to think he was the one who made it hard. It was erect because of seeing myself on the video getting fucked.
“Lie down in the chair and take off the bottoms,” Derrick told me as he was staring at my breasts.
I took a deep breath, laid on my back in the plush lounge chair, and slowly pulled down the bikini bottoms. I sat up and removed them from around my feet, lay back down, and covered my hard cock with my hands. I looked up at the boy and he was looking over my naked body. I could tell by the look on his face he liked what he saw. Derrick reached down and pried my hands off of my cock and I didn’t resist.
Derrick didn’t say anything about my erection and reached over to the small table next to the lounge chair and picked up my coconut-scented suntan lotion. I was also silent as the boy poured a large amount of the lotion over my breasts and then over my cock.
“Put your hand above your head,” the boy told me.
I did as he told me. I made a whimpering gasp when Derrick reached down and put his hand around my erect penis.
“Don’t, please,” I told him.
Derrick grinned, but didn’t say anything as he slowly started to stroke my cock. I started making whimpering moans of pleasure as the boy slowly played with my cock. I didn’t want to enjoy the sensation, but I couldn’t help it. I had not had anyone touch my cock in months, besides myself, and I always enjoyed it when a man jerked me off much more than when I did it to myself.
“Play with your tits,” Derrick ordered me as he started stroking my cock harder.
I lowered my hands to my lotion-covered breasts and started playing with my nipples. My whimpers of pleasure soon turned into louder moans of pleasure as Derrick started jerking my cock harder and faster as I started to tweak and pinch my erect nipples harder.
“Uh, fuck!” I gasped out loudly when Derrick penetrated my butt with his finger.
“You like that, don’t you?” he asked. “You like getting your girl pussy fingered, don’t you?”
“No…uh God…no,” I lied.
It felt very good and even better when Derrick started twisting his finger inside me, moving it around, and trusting it in and out of my butthole. I started moaning louder as he worked his finger in my ass. I gave another loud gasping moan when the boy placed a second finger inside me and it felt even better.
Derrick jerked me off and fingered my ass until I had an orgasm. When I came, my body jerked, and I moaned out as cum exploded from my cock and landed on my stomach and my breasts. Derrick kept stroking my dick furiously and finger fucking my ass hard even after my orgasm ended.
“Uhhh, stop, please…stop Derrick,” I whined and whimpered as the boy kept using his hand on my cock.
My penis had become sensitive, but the boy kept going and I placed my arms above my head. He kept jerking me and fingering me until I was aroused once more and my cock stayed erect and he finally stopped.
“That was awesome,” he told me as he looked over my body again. “You sure shot some huge loads of cum.”
I didn’t say anything. I was ashamed of myself for enjoying what he did to me as much as I did. I watched as the boy ran his fingers through the cum and gathered what he could on his fingers. Derrick then pressed his fingers to my lips and I opened my mouth without thinking and sucked and licked his fingers to taste my cum.
Derrick chuckled as he watched me eat my cum. “Yeah, you like that, don’t you?” he asked his rhetorical question. “Such a cum eating whore,” he told me as he shoved his fingers deeper into my mouth until I gagged on them. “I got some more for you.”
Derrick pulled his fingers out of my mouth and replaced them with the two fingers that has been in my butthole. I eagerly sucked them as he thrust them in and out of my mouth. The boy chucked.
“Such a nasty, slut,” he told me as I sucked my finger. “You like the taste of your ass pussy, don’t you?” he taunted me.
I didn’t say anything after he pulled his fingers out of my mouth. I had no problem going ass to mouth, and I did enjoy it. I practiced great personal hygiene and knew how to keep my “ass pussy” clean since I first started having sex when I was sixteen.
Derrick pulled the drawstrings on his athletic shorts and pulled them down to his knees. His cock sprang loose. I looked over at his crotch and made a gasp of surprise when I saw his erect penis.
Derrick’s cock was larger than I would ever would have thought. Like how I felt about his looks, I found his penis unattractive. It looked to be about eight inches long and thick. I was surprised such a skinny boy had such a large penis. It jutted out from his black pubic hairs and looked a little comical, being so large and his body as thin as it was.
What made his cock ugly to me was the tip. Derrick had a large, bulbous, mushroom cock head that was thicker than the girth of his shaft. I never cared for the look of a penis shape like that. Still, I wanted him in my mouth. That was another shock for me.
I know the circumstance of why I was about to suck his cock was that he was blackmailing me, but I was sexually aroused from him jerking me off and how he kept doing it after I had an orgasm. I know I should not be turned on, but I was. Even though my erection made my arousal obvious to Derrick that I was aroused, I didn’t want him to know how turned on I was, so I was just going to suck his cock and make him orgasm as fast as possible.
Derrick had other plans, however. “Do it nice and slow and make me feel real good, like you did in your porn video,” he told me. “I want my first blowjob to be a good one and I want you to swallow my cum.” His comment about his first blowjob confirmed what I had already suspected; Derrick was a virgin.
I nodded my head and took his large, hard cock in my hand. It was big, but I had done the porn scenes and the men in them had been about the same size and the black man was much larger, so I knew I could handle it and make the boy feel good. I lowered my head to his cock.
My past had come back to haunt me, as they say. Even though I had told him I didn’t care if he sent the video, I didn’t want people to see it and know of my past. Derrick had me under his complete control with the blackmail, so I knew I had to do as he told me to. I knew I had to give him a seductive blowjob and not just suck his cock and make him orgasm quickly.
I started by running my tongue over the boy’s hairy scrotum and then up and down his shaft and licking the pre-cum off the tip of his cock. I repeated that several times as Derrick moaned in pleasure. Just as I was about to take the boy’s penis in my mouth, he placed his hand on the back of my head and grabbed my ponytail.
“Don’t use your hand,” he told me, “just your mouth and look up at me as you suck my dick.”
I took my hand off his shaft and placed both of my hands on his butt cheeks and looked up at the boy as I took him into my mouth. Since Derrick wanted me to go slow, I only took about two inches of his cock into my mouth and started running my tongue over the large mushroom tip. As I did, I began to rethink how I felt about such a cock head. I was enjoying how the bulbous head felt in my mouth.
After teasing his cock and listening to his low moans of pleasure for several moments I took the boy deeper into my mouth and down my throat and deep-throated him. Even though his cock was above average in size, I could deep-throat the boy. I had deep-throated the huge cock of the black man in the porn scene I did. When my lips were pressed against Derrick’s pubic hairs, I held my head still for a few seconds.
“Uh, fuck, Bella, that feels good,” Derrick told me. “Damn, you like sucking dick, don’t you?”
I didn’t answer him and I knew he didn’t want an answer, but I did enjoy cocksucking a great deal. I was also enjoying giving Derrick a blowjob. While the boy was not very attractive and the circumstances of why I was sucking his cock were because of blackmail, I was still enjoying it. It had been a long time since I had given a blowjob and I was aroused from him jerking me off earlier and my cock was still hard.
I pulled my head back and took my mouth off his penis. “Can…can I touch myself?” I asked.
Derrick looked down and grinned at me. “You’re horny slut aren’t you,” he told me. “Sure, jerk that little girl cock while you suck mine.”
My cock was average and not little, but compared to Derrick’s, it was. I put my mouth back on his penis and started to stroke my cock with my right hand. As I was giving the boy a blow job and jerking my cock, I heard his cell phone chime, but we both ignored it. Both Derrick and I were enjoying what we were doing too much to stop.
I slowly sucked his cock, stroked mine, and deep-throated the boy several more times. His cell phone chimed a few more times and finally Derrick felt the need to check it. He pulled my head back by my ponytail and picked his phone up off the table. As he was checking his phone, I kept running my hand over his penis and using my other hand on myself.
“Shit,” the boy muttered. “I need to go soon.” Derrick put his phone back on the table and looked down at me. “ Well, seems I won’t be able to fuck you today and you need to hurry and finish sucking me off.”
“I…you…fucking me was not part of our deal,” I told the boy. “We agreed to just a blowjob.”
Derrick laughed. “We never agreed on any such thing. Do you think I am going to waste such good blackmail material on just getting my cock sucked by a porn whore?” he told me. “Bella, these videos are worth a lot more than that. You and I are going to have a lot of fun together this summer.”
I swallowed hard and was about to tell him I was not going to let him fuck me ever when the boy pushed my head back to his cock and I again took him into my mouth.
“Go faster this time,” he told me.
I started bobbing my head back and forth as I sucked the boy’s cock faster. Derrick started thrusting his hips forward and soon we synced up our rhythm and I gagged a few times when his cock went down my throat unexpectedly. I stopped stroking my cock and put both hands on his penis and jerked him off as I gave him a blowjob to help the boy cum faster.
It didn’t take Derrick long to cum. He pushed my head down and made a series of grunting moans as his cum shot into my mouth. He came a lot but I managed to swallow all of the warm, thick, sticky fluid. I enjoyed how his cum exploded in my mouth and down my throat. I had not tasted anyone else’s cum in so long besides my own and I enjoyed his immensely.
I enjoyed it so much that after he pulled his cock out of my mouth and let go of my ponytail, I put the tip of his cock in my mouth. I started milking his cock with my hand to try and coax as much of the boy’s fluid I could into my mouth.
I heard Derrick laugh at me and he then pulled my head back and took a step backwards. “Damn, that was great, Bella,” he told me. “You sure like cum, don’t you?”
I didn’t answer, but watched the boy pull up his underwear and shorts and put his phone in his pocket.
“A shame I didn’t get to fuck that ass pussy today. Next time I will and I’ll make sure I can stay longer and we can have more fun together,” he told me.
“No,” I told the boy, but my voice was low and didn’t hold much conviction to it. “That…that was it, Derrick. You got what you wanted.”
The boy chuckled and reached down and caressed my cheek with his fingers. I didn’t pull away.
“No, Bella, I didn’t get all I wanted. I told you we are going to have a lot of fun together this summer,” he told me. “You know you enjoyed it as well. You know you liked how I jerked you off and you liked sucking my cock and eating my cum.”
“I…I didn’t,” I told him.
“Liar,” he replied.
I was lying. I did enjoy when he masturbated me and made me cum; I did enjoy sucking his cock, and I did enjoy swallowing his cum. I felt ashamed of myself for it, but I did enjoy it and part of me was disappointed he was not going to fuck me. I just didn’t want him to know it.
“I will make one deal with you, though,” he told me.
“What?” I asked suspiciously.
“You’ll continue to suck my cock, but I won’t fuck you until you ask for it,” he told me with confidence.
I nodded my head. “Okay. I don’t have a choice about the blowjobs, but I can promise you that I will never ask you to fuck me,” I told the boy with confidence.
Derrick chuckled. “We’ll see. I doubt you can resist because you’re such a slut and I bet you will fuck just about any guy,” he insulted me. “I have to go but I may see you tomorrow. Maybe look better next time I see you. Put on some makeup and I like your hair down.”
After I watched Derrick walk through the gate I picked up the suntan lotion, and poured some on my hard cock and the fingers of my left hand. I was still horny and wanted to cum so bad I didn’t even wait until I went into my house. I masturbated outside by my pool as I used two fingers to fuck my ass. The entire time I thought of Derrick fucking me. I didn’t want to fantasize about him but couldn’t help it. I thought about how his large cock and his large, ugly mushroom-shaped tip would feel going in and out of my ass.
I orgasmed quickly, used my fingers to gather up the cum on my stomach, and licked and sucked them clean. With my sexual desires now sated, I told myself that I was not going to let the boy use me again like he just had and I sure was not going to let him fuck me. I would think of some way to get out of being blackmailed by him.