I am currently thirty-four-years-old and this story took place when I was thirty-two and had an affair with an eighteen-year-old boy. The affair started because of him blackmailing me for sex but it quickly escalated to me not just desiring the young boy, but becoming obsessed with him and how he treated me.
His idea of sex was more perversion. He treated me like his personal whore. The sex involved things I had never done before, and I enjoyed it a great deal.
I am not going to do the whole origin or background story of my life or when I started transitioning and all the boring stuff, but just a little about my past, I will include a little that has to do with the story. I started my transition when I was a teenager and had supportive parents.
When I was nineteen, I moved to Miami to live with a friend of mine who was also transgender. I needed money to continue college and also to save up to get breast implants. My friend told me I could make more money working in Miami than where I lived.
With tips, I was making decent money as a waitress for a Michelin Star restaurant, but not enough. My roommate worked part-time as an escort, yes prostitute, and I decided to give it a try. I worked as an escort for about eight months and the money was great. Being transgender, men would pay a nice sum of money for an hour to fulfill a fetish of fucking a transgender girl. Some even paid for an entire evening with me.
I then got into the adult film industry. I only did four porn scenes. The first was a casting scene for a first timer and the director liked what he saw in me. One thing he liked was that when I get very aroused, I orgasm from just having my ass fucked. I can cum from just anal sex without having my small cock touched.
I have a small cock. When erect, it’s thin and only six inches long. When not erect, it is extremely small, and doing the tuck thing is rarely required. I didn’t care and like that my cock was small and thin, makes me feel more feminine.
The next two porn scenes were transsexual babysitter porn scenes. Being only nineteen and the fact I had braces, I fit the part as a teenage babysitter well and the director would have me put my hair in pigtails.
The last porn scene I did was with a black male actor who was famous in the industry because of his thick, twelve-inch cock. God, did he fuck me with his monster cock! The scene lasted close to an hour, and he brutally fucked me almost non-stop with his enormous cock. I had to call out for a break two times because he was so big. I had three orgasms during that scene. The first two were from him just fucking me and the last one was when I was on my back and he was relentlessly pounding my asshole with his massive dick and I jerked my little cock until I came.
That was my period in the sex business, and I went back to school and was able to get my breast implants. I graduated with a degree in computer science and took a job with a well-known company in Atlanta.
When I was thirty, I bought a house in one of the nice Atlanta suburbs, and after the Covid pandemic; I worked mostly at home. I only went into the office about three or four times a month. I also met a man, and we started dating.
People may think that with my past in the adult sex business, I would be a sexual freak or into some kinky sexual things, but I was not. I was a typical girl who believed in romance and love. My personal sex life was vanilla. I did just the normal things a girl does when being intimate with a man. Giving blowjobs and having intercourse. I never even had a one-night stand before, well, besides when I was an escort.
I am strictly a bottom girl and don’t enjoy topping a man. I have when I was working as an escort when my client wanted me to fuck him and he paid extra for it, but I didn’t enjoy it. Sure, it felt good, but it didn’t turn me on and sometimes I had a hard time keeping an erection when fucking a man.
I was happy. I had a nice three-bedroom, two-bathroom house with a swimming pool I used often, I was dating a man I was in love with and thought things were going great. I had a great job that paid extremely well, and I was somewhat active with the neighborhood community.
Yes, my neighbors knew I was transgender. I never hid that, but also never flaunted it either.
After a little over a year of dating Tim, my love life went downhill. I found out he was cheating on me almost ever since we started dating and that I didn’t mean to him what I thought I did. He didn’t love me and was just using me as a fetish. The day he broke up with me, Tim told me he had just gotten engaged to the woman he was seeing.
About four months after my relationship with Tim ended, I was still heartbroken and did one of the worst things I could have done. I had sex with my married neighbor, who had two kids.
No one took the initiative to plan it. His wife was with the kids visiting his in-laws. Jerry came over to fix my clogged garbage disposal. I was still sad and lonely and asked him to stay and talk. The next thing I knew, we were kissing on the sofa and then I started sucking his cock and let him fuck me on my sofa.
After he was done, we both felt terrible. Jerry left immediately after we both promised it would never happen again and we would not tell anyone. I felt so guilty and I knew he did as well. I also think he felt guilty about sucking my small cock and fucking a transgender woman. No one ever knew, or so I thought.
It was about five months after that night and I was feeling much better and I rarely thought of Tim at all. It was around the first of June; the weather was getting hotter, and I decided it was time to have my pool cleaned for the summer.
I wore a skimpy bikini and since no one was going to see me so I decided on my red thong bikini and admired myself in the mirror. Even without makeup, I thought I was attractive.
I stand five foot, seven inches tall with smooth skin that is hairless from the neck down and great legs. My long, dark brown, straight hair came down to the middle of my back. I have thirty-six C breasts. They are nice and firm and cost a pretty penny to have done, but I wanted them done right, so I paid a great deal for them. I had seen too many botched breast jobs. You get what you pay for.
I have an amazing ass. It is a nice bubble butt shape to it and it’s well, fantastic!
I stay in shape by going to the gym and practicing yoga, but my favorite form of exercise is riding my bike and hiking. I enjoy the outdoors.
Besides being attractive, I have an outstanding personality. I am a kind, caring person, and sensitive. I cry at movies and even TV commercials. While I don’t get easily offended, I do cry when someone hurts my feelings. I am a nice person.
As I mentioned, I was not into much kink sexually, but I am a sexual and sensual person who enjoys sex a great deal as well as intimacy. I love kissing and cuddling and appropriate public displays of affection. Even though I am a bottom girl, that does not mean I am a submissive girl when it comes to sex, but not a dominant lover either. I love wearing sexy underwear and lingerie and outfits and teasing and initiating sex with my lover.
When I worked as an escort when I was much younger, some men wanted to call me a whore and a slut while they fucked me or when I sucked their cocks, but I would have none of that and told them not to call me such names. I didn’t get into being spanked or having my hair pulled, either. I don’t do pain well.
I don’t mind and enjoy it when the man I am dating takes sexy pics of me in my lingerie, but I don’t do full nude photos of myself or any vulgar poses.
After looking over myself for several seconds, I grabbed my book, my glasses since I didn’t have my contacts in, a towel, coconut-scented suntan oil, and headed out the sliding glass doors in the back to my pool.
I was reading the latest book in a series of erotic novels about a young transgender private detective. I was reading a chapter where the protagonist was following the prime suspect in the theft of a famous painting from a private art collector’s home and she followed him into a fetish sex club.
I was at a passage where she met two handsome men and they took her into one of the private rooms. She was on the bed on her back while one man was fucking her while he was stroking her hard cock and the other man was kneeling next to her face and she was sucking his dick.
My small penis became erect, and I was using my left hand to gently rub it against my bikini bottoms. As I was reading the passage I was thinking how long it was since I had sex, which was when my married neighbor fucked me, and was thinking that soon I was going to have to go inside, get my dildo, and fuck myself while I masturbated.
My reading of the explicit passage and my thoughts were interrupted when I heard the gate to my privacy fence open. I turned my head and saw Derrick walking through the gate. I quickly placed a towel over my lap to cover up my erection. I may have a small penis but the bikini bottoms were skimpy thong cut and didn’t hide much at all.
Derrick lived on the same block several houses down from mine with his parents. I didn’t know his parents well, even though I was always invited to his father’s annual Fourth of July cookout and pool party. The entire block was always invited. It was a big event in the neighborhood. I can’t even remember saying more than a few words to Derrick in the years I lived in the neighborhood.
What I did know of the boy was that he was seventeen or maybe eighteen then, and that was about it. What I found out later about him when he started fucking me was quite a lot.
Derrick was not a handsome boy at all, or even cute. He was eighteen at the time, tall and lanky. He was skinny, had long limbs, narrow shoulders, and not much muscle tone. He must have been about six feet, one inch tall at the age of eighteen. The boy had thick, black hair that came down past his ears and always looked like it needed to be brushed or combed.
Derrick was wearing a pair of baggy cargo shorts and a tee shirt. I noticed he had hairy legs. Much hairier than most boys at age eighteen, and the same black hairs covered his arms as well. The boy had an acute case of black head breaking out on his forehead. No, he was not an attractive young man at all.
The things I learned about Derrick were that he was smart, extremely smart, with an IQ that was at the genius level. He had just graduated high school that year and was going to MIT in the fall. He loved anything to do with math, computers, and all types of electronic gadgets. He was a geek and a nerd.
Now, there is nothing wrong with being a geek or a nerd. I was a huge nerd when I was younger and in high school. I was not a math nerd, though. My nerdiness was that I was into theater and fantasy and even belonged to a Dungeons and Dragons group.
I imagined Derrick was bullied in school and rejected by girls. I could relate to and even sympathize with him being bullied. Being transgender and growing up in Louisiana, I was bullied as well.
Maybe him being bullied and rejected by girls made Derrick the way he was and affected his personality. Derrick had very little social graces, and he was cruel and a bully himself. He was not a physical bully, but an intellectual bully and used words to bully people.
I also discovered the boy was a sexual pervert and had deviant ideas about sex, and that he watched a great deal of porn. The genre of porn he enjoyed the most was the more taboo type and where the female actresses were abused verbally and physically.
Of course, that day when he walked into my backyard, I knew nothing of that, but I was about to find out.
“Hi, Bella,” Derrick said as he walked towards me.
Bella is not my real name, but the name I will use in my story. It was the name I used when I was an escort and in my short stint in porn.
“What are you doing here?” I asked. “It’s rude to just walk into my backyard uninvited.”
He didn’t answer and sat down in the lounge chair next to the one I was lying on. The boy then pulled out his phone from the pocket of his shorts.
“I want to show you something,” he told me and was grinning. “I think you will find it very interesting.”
Derrick turned his phone around so I could see the screen. On the phone screen was a younger me on my knees, having my mouth stretched apart by a huge black cock. It was the porn scene I made when I was nineteen.
I was stunned for a moment but quickly recovered. “Why are you showing me this? I don’t enjoy porn,” I told him.
Derrick laughed. “I think it’s sexy and amazed you could handle such a gigantic cock in your mouth.”
“Me?” I asked as if I was confused. “That’s not me.”
The boy laughed again and then used his finger to fast forward the scene. He stopped it and I saw myself riding that enormous dick in a reverse cowgirl position and my face was contorted in pleasure. My loud moans and telling my scene partner how big his cock was and how deep it was inside me could be heard. Despite my younger age, shorter hair, smaller breasts (I hadn’t gotten implants yet), and a face contorted in pleasure, it was clearly me.
“That’s not me,” I told him again, but this time with less conviction in my voice. “Now turn it off.”
“Not yet. It’s getting to one of the best parts.”
I looked back at the phone. A younger me was crying out and making loud, moaning grunts of pleasure. Tears were running down my face, not from pain but from the pleasure of such a gigantic cock in me.
“I’m cumming, oh God, I’m cumming,” I cried out and clear pre-cum leaked out of my cock and ran down the shaft.
The black man fucking me grabbed my wrists and held me tight as he started to thrust up into me hard. With each thrust as his huge cock hit my prostate, thick cum squirted out of my penis. The pleasure caused me to throw my head back and cry out again and again.
When I came from getting fucked, it was always like that. Clear, thin precum leaked out of my cock like a faucet turned on low. When I had my orgasm, my thick cum would spurt out of my penis with each thrust of the man’s cock into me.
“That’s not me,” I repeated, but with much less conviction. It was easy to tell it was me.
Derrick grinned. “Yes it is, but I think we are both going to know that this next video is you,” he told me.
The boy then pulled up another video on his phone and showed it to me. This one was of me five months ago and I was on my knees once more, this time in front of my sofa and sucking my married neighbor’s cock. The video was shot from my backyard.
“How did you get this?” I asked, once again stunned.
“I made it, stupid,” he told me. “I made it when Mr. Jenkins fucked you that night. I like this part.”
I looked back at the phone and Derrick once again fast-forwarded the video. He stopped it and it showed me on the sofa with my legs up over my head, and Jerry was fucking me hard. You could hear my loud moans. I am loud when I get fucked and Jerry’s masculine grunts and me telling Jerry to fuck my ass harder.
“You…you…that’s illegal to spy on me and stalk me and…I could call the police,” I told the boy.
Derrick laughed again. “You could, and I could send this video to Mrs. Jenkins. I have lots of videos of you, Bella. You really need to close your curtains in your bedroom when you get undressed,” the boy gave me a sly look, “and when you fuck yourself with your dildo and jerk off.”
I swallowed hard. “You fucking pervert. I should call the police or at least tell your parents,” I threatened, but I knew it was an empty threat.
“But you won’t,” he told me, and he was right.
I didn’t want the porn scene put out there for my neighbors to see. I didn’t want any videos of me masturbating sent to anyone, and I certainly didn’t want Jerry’s wife to see him fucking me. I didn’t want to ruin a marriage.
I don’t know why the boy waited so long to confront me with the videos. Maybe he needed to work up his courage to blackmail me.
“What…what do you want?” I asked in a defeated voice. “I have money.”
Derrick shook his head. “I don’t want your money, Bella. I want what Mr. Jenkins got that night. I want it for as long as I want to get it,” he told me. “I want you to be my whore, Bella.” Except he didn’t just use the word whore, he used the derogatory term for a transgender that I can’t use in the story, but it rhymes with the word nanny.
“That is not going to happen,” I told Derrick sternly. “You need to go home Derrick and don’t ever come here again.”
I moved the towel from my lap. My erection was now gone, and started to get up and go into the house. Derrick grabbed my arm and pushed me back down on the lounge chair. I made a whimpering, grunting sound. I was calling his bluff.
“Don’t leave yet, Bella. I want you to see me send the video to Mrs. Jenkins. My dad has everyone’s email address for his party invite,” the boy told me.
He started pressing his thumbs on his phone screen, looked at me, and grinned. “Do you want me to CC you, Bella? You may want a reminder of the night you whored yourself out to a married man with kids and wrecked a marriage.”
“You…you wouldn’t,” I said.
“I would and I am going to unless you give me what I want,” he told me.
I knew then that the boy was serious. He would do what he was threatening to do.
“I’ll…I’ll use my mouth on you, but that’s it and just this one time,” I offered as I gave in to his blackmail.
Derrick grinned but shook his head. “No, you are going to suck my cock and then I am going to play with you for a while.”
I nodded. How bad could it be? It was just one blowjob. I had no idea what he meant by “play with me” though, but it couldn’t be bad and he didn’t say fuck me.
“Ok, but just this once,” I told him.
Without a word, the boy stood up while I sat up on the lounge chair with my feet on the ground so I was close to Derrick’s crotch. I was ninety-nine percent sure Derrick was a virgin, and I highly suspected this was going to be his first blowjob, so I knew it would be over quickly. I was going to put him in my mouth and suck his cock as fast and hard as I could to make get the ordeal over.
“Take off your top, Bella. I want to see your tits,” the boy told me.
I slowly reached behind my back and unhooked my bikini top and removed it to expose my breasts. Derrick inhaled sharply.
“Nice,” he told me. “They look so real.”
The boy then pulled down his baggy cargo shorts and his white briefs at the same time. I gasped when I saw his cock. He was huge! Derrick was a lot bigger than I thought he would be. His cock was already erect and it must have been eight or eight and a half inches long and thick. It jutted out from his thick mass of black, coarse pubic hair. I even found his cock ugly. It was not the type of penis I thought was sexy. It had a huge, mushroom, bulbous head that was thicker than his thick shaft.
I was going to make him cum quickly and get this over with. I looked up at Derrick. “Don’t cum in my mouth,” I told him. He just grinned.
I put my right hand on his cock, moved my head down, parted my lips, and took the boy’s huge tip in my mouth. As soon as his cock entered my wet mouth, Derrick let out a masculine moan of pleasure. I then started moving my head back and forth rapidly as I sucked his cock.
After about twenty seconds of me sucking Derrick’s cock, he reached down and grabbed a handful of my long hair, and pulled my head back hard. It hurt, and I whimpered from the pain.
“Not so fast,” he told me as he kept pulling my hair. “I want my first blowjob to be a good one. Use your whore mouth slower.”
“I’m not a whore,” I told the boy.
Derrick laughed at me. “You did porn, and you got fucked by a married man, Bella. You are a whore and now you are my whore,” he told me and pushed my head back down to his cock.
When I opened my mouth to suck it again, Derrick pulled my head back once more and held it still. I whimpered again. Derrick then took his large penis in his right hand and started slapping my face with it.
“Stop,” I whined out.
I didn’t like that and found it humiliating, but something strange started to happen. My cock started to get hard, and I was getting turned on. As Derrick slapped my face with his cock, I tried to fight it, but I was getting aroused.
“Don’t,” I whined out, but my voice held less conviction and I sounded as if I didn’t mean it.
Derrick picked up on the tone of my voice and laughed at me again. “Now suck it again,” he told me and shoved his cock in my mouth.
I took the boy’s large penis in my mouth a second time, but this time it was different. I didn’t want to suck it fast and hard and to make him cum quickly. This time I wanted to suck his cock the way I enjoyed sucking cock. I wanted to make love to his penis with my mouth.
I dropped my left hand down to my small, erect penis and started rubbing it through the bikini bottoms, and placed my right hand on the boy’s thick shaft. I then started moving my head slowly as my tongue ran over the large tip of his cock that was in my mouth. I began to appreciate the large mushroom head. I tasted his pre-cum and let out an involuntary moan of pleasure at the taste.
I not only made love to Derrick’s cock with my mouth, I worshipped it. I love giving slow, sensual blowjobs as well as wet sloppy fast ones, and I started to give the boy a slow sensual blowjob. I made sure my saliva ran out of my mouth to cover his shaft and work his cock with my hand as I sucked him and ran my tongue up and down his shaft.
I was making sensual moans of pleasure as I sucked Derrick’s cock and then made a whimpering sound as the boy reached down and started pinching my nipples hard. I did enjoy my nipples played with and pinched, but not as hard as the boy was pinching me. But I didn’t tell him to stop because it aroused me even more.
Derrick was making masculine moans of pleasure as I sucked his cock and I pulled my bikini bottom to the side to free my cock and started stroking it hard.
“Don’t touch yourself,” the boy told me. “I don’t want you to cum yet.”
I ignored him and kept stroking my small penis. Derrick pinched my nipple harder and twisted it, causing me to give a muffled whimper of pain, and grabbed my wrist tight and pulled my hand away from my cock.
“I told you to stop, you whore,” he said in a harsh and commanding tone. Derrick didn’t just call me a whore but used derogatory language.
I pulled my head back and the boy’s cock slipped out of my mouth and I looked up at Derrick. “I’m sorry, I’m sorry,” I told him as I whimpered still.
I could not believe what I just did! I was apologizing to an eighteen-year-old boy who was blackmailing me to suck his cock, who was hurting me, and who was calling me a whore and using a word that was a derogatory term for a transgender.
“Put it back in your mouth,” the boy commanded me, and I did.
It didn’t take long before I heard Derrick’s moans of pleasure become grunts of pleasure and felt his body tense. I knew he was going to cum. I started sucking his cock faster and harder as I stroked his shaft rapidly. I know I told the boy not to cum in my mouth, but now I wanted him to. I wanted to feel his warm cum spray into my mouth and down my throat and taste it.
Derrick’s cum shot into my mouth and my eyes opened wide because of the abundant amount of warm, thick, sticky fluid that sprayed into my mouth and down my throat. I managed to take all of it and swallowed the boy’s cum as Derrick made loud grunts of pleasure.
I kept sucking and milking his cock for more cum until he grabbed a handful of my hair and pulled my head back.
“Fuck, that was awesome,” he told me. “You sure like eating cum like a good whore, don’t you.” It was not a question.
I didn’t respond. I wiped my face and looked up at Derrick. I did enjoy sucking his large cock and eating his cum, but I didn’t want him to know that.
“You…you got what you wanted,” I said.
Derrick laughed at me again. “Bella, I didn’t get even half of what I want from you,” he told me. “I’m still hard and you are going to do that again.”
I looked down and saw the boy was indeed still erect. Before I could say a word, Derrick pushed my head back to his cock, and I opened my mouth once more. I did want to suck his cock again, except this time I didn’t suck the boy’s cock. Derrick fucked my mouth.
Derrick held my head still by my hair and then placed his other hand under my chin. The boy then started thrusting his hips and driving his cock into my mouth hard and fast. I placed my hands on his thighs to push him away, but he told me to keep my arms down at my sides and not touch my small, hard cock.
It was not long before I started gagging and choking as the boy kept thrusting his hips and driving his cock down my throat. My saliva soon turned thick and mucus-like and was pouring out of my mouth, down my chin, and onto my chest. I was making loud gulping sounds as he fucked my mouth and tears formed in my eyes.
After several minutes, Derrick pulled my head back by my hair again and took his thick eight-inch cock out of my mouth. I gagged and coughed as I caught my breath and once I did, he again started fucking my mouth.
I was surprised at how hard my cock was. It was aching, and I was aroused by how the boy was treating me and abusing my mouth with his cock.
“That turns you on, doesn’t it? You like being my cock sucking whore, don’t you, Bella?” he taunted me.
“No,” I lied. It was turning me on.
“Bullshit,” Derrick told me and chuckled and once again started fucking my mouth with his large penis. Derrick repeated that process several more times and then grunted out he was going to cum again. I eagerly for him to cum in my mouth again, but he pulled back, let go of my chin, and rapidly stroked his cock.
I knew what he was going to do. I closed my eyes and then felt his cum splatter on my face. It was once again a large amount of cum and it landed on my closed eyes, forehead, nose, cheeks, and mouth. I ran my tongue around my mouth, licking up what I could. I did enjoy having a man cum over my face and body.
When the boy’s orgasm ended, he once again laughed at me and called me a cum slut; no he called me his cum slut. I reached over to grab my towel to wipe my face, but Derrick grabbed my wrist to prevent me.
“Not yet. Lie back and put your hands above your head,” he ordered me.
I did as he told me, except I put my hands over my hard cock. I didn’t want the boy to see my erection and to know what he was doing to me turned me on.
“Can…can you at least let me wipe my eyes?” I asked, my voice timid and even a little frightened. I knew from experience that a man’s cum would burn my eyes if I opened them.
I could not see but felt my towel being dabbed on my eyes and then wiped. Derrick was wiping my eyes for me. I opened them and looked up at the boy. Derrick was frowning.
“I told you to put your arms above your head,” he said, grabbed my wrists, and pulled my arms up. He chuckled as he looked down at my penis. My bikini bottoms were pulled to the side, and my cock was exposed.
“You sure have a small she-dick, don’t you, Bella? It looks even smaller than in the videos,” he told me.
“I’m…I’m sorry,” I apologized. I could have kicked myself! I never apologized for the size or lack of size of my penis and I felt ashamed of myself for apologizing to this mean eighteen-year-old boy.
“Don’t be sorry. I like it small. It suits a whore like you,” he told me. “Now, don’t move.”
I watched as Derrick grabbed the suntan oil from the table and he poured a generous amount of the lotion over my breasts, stomach, and erect cock and started to rub over my body.
The boy started at my breasts and nipples and I let out an involuntary moan of pleasure. He then rubbed the oil over my stomach and when he got to my hard penis, I flinched.
“It’s hard, Bella. You must have enjoyed sucking my cock,” he taunted.
“No,” I lied, and he just laughed and knew I was lying.
I flinched again as the boy wrapped his hand around my small erection and I looked down. His fingers were long and bony. I then moaned out in pleasure again as the boy started slowly stroking my slick cock.
Derrick continued to stroke my cock slowly with his right hand and then started playing with my nipples with his left. While it felt great, I wanted him to go faster so I could cum, but I was not going to give the boy the satisfaction of telling him that. Instead, I started thrusting my hips up, hoping he would go faster. My fingers dug into the soft pad of the lounge chair.
He didn’t and just teased me. The need to cum soon became unbearable. “Please, Derrick, please go faster,” I asked. No, I didn’t ask, I pleaded with him. The boy laughed again.
“Not yet, Bella,” he told me. “Only good whores get to cum and you haven’t shown me you are a good whore yet,” he kept taunting me.
I didn’t say anything. I was not a whore! Derrick let go of my cock and I let out a whimper of disappointment. The boy then started to run his index finger over the tip of my cock. He ran his finger through my pre-cum and spread it over the head of my penis. I moaned out again.
The boy once again started to stroke my cock slowly, and I was moaning and whimpering with the desire to orgasm, but he didn’t let me. He would stop when I was about to cum. He was teasing me and edging me.
I had a love/hate relationship with being edged. I hated it because I was denied an orgasm, but loved it because it aroused me a great deal. Once, when Derrick stopped, he straddled my chest and put his large erect cock to my face and I immediately put him in my mouth again and started to suck it. He pulled out after about a minute and went back to slowly stroking my cock.
“Please, Derrick, please let me cum,” I was begging him now. With my need to orgasm, all the pride and stubbornness I had was now gone, and I was pleading with the cruel boy.
“What are you, Bella?” he asked.
“I’m a whore,” I told him.
“Whose whore are you?” he said after he chuckled.
“Yours. I’m your whore. Oh God, please let me cum,” I begged again and had tears in my eyes. Derrick had broken me and done it quickly.
He let go of my cock. “Turn over and keep your hands above your head and lift that ass for me,” he ordered me.
“No, Derrick, please. Not…” I started to protest. I suspected he wanted to fuck me.
“Do it, Bella, or I swear to God I will send that video to Mrs. Jenkins,” he interrupted me.
I knew he was serious, so I did as he told me. Derrick also interrupted me before I could finish. God help me, but I did want this ugly, eighteen-year-old boy with a large ugly cock to fuck me. I was too aroused to deny him that pleasure, and I wanted it. I was trying to tell him not here outside by the pool but for us to go inside. I was so aroused that I knew if he fucked me, I would cum.
I turned over and put my arms above my head, brought my knees up so my ass would be lifted for the boy. I looked over my shoulder. Derrick once again picked up the bottle of suntan oil. He poured a great deal of it over my ass and then more down my butt crack.
“You have a great ass, Bella,” he commented as he admired my butt.
I did have a great ass. It was a nice bubble shape, and I exercised to keep it firm and shapely. I was proud of my ass.
Derrick pulled my bikini bottoms down to my knees. “Spread your ass apart for me,” he commanded.
I immediately put my hands on my ass cheeks and spread myself open for the boy.
“You have a sexy pussy, Bella,” he commented. Again he used the word that derogatory word before the word pussy. Derrick would always refer to my asshole as that.
I moaned out when the boy pushed his long finger into my asshole. It felt good. I kept moaning as Derrick finger fucked me and then gave a louder grunting moan of pleasure when he put a second finger inside me.
“Fuck me, Derrick, please fuck me,” I begged.
“So now you want it?” he asked.
“Yes, please, yes I do,” I admitted.
Derrick laughed once more and took his fingers out of my ass. I felt him kneel on behind me and then the tip of his cock pressed against my tight hole. I once again gave a grunting moan as he entered my asshole which was lubricated by the suntan oil. I could feel my long neglected asshole stretch as the large mushroom tip entered me and then closed around his thick shaft. Derrick started to fuck me.
He started slow at first, but soon he started to go harder and faster. God, it felt amazing to have his thick eight-inch cock in my ass. The only thing I had fucked my ass for the past several months was my dildo when I masturbated. A real cock felt wonderful.
I was moaning loudly and calling out to God as he fucked me and enjoyed his masculine grunts of pleasure. Derrick then reached down, grabbed a handful of my long hair, and pulled my head off the lounge chair. I whimpered loudly, but I didn’t care that it hurt. The pain seemed to make the pleasure of getting fucked even more intense. The boy kept calling me a whore and a slut as he fucked me and pulled my hair hard.
“Oh, fuck… oh God, I’m going to cum…oh God, Derrick, you’re going to make me cum!” I cried out.
Just from getting fucked, I had an orgasm. My pre-cum started to run out of my cock, and then I started to orgasm. I kept moaning loudly as the boy thrust into me hard and with each thrust I ejaculated my thick cum in spurts. It felt amazing. I loved having an orgasm that way. It was always much more intense.
Unlike most transgender women, my cum or my erection was never affected by hormones. Well, that’s not true. When I was sixteen and first started my HRT treatment, I never had a problem getting an erection, but my cum was thinner and clear. By the time I was in my late teens, around eighteen, that changed and my cum was now thick and abundant when I orgasmed.
I never had a problem not having an orgasm. Quite the opposite; I always came rather quickly and when I was younger, I suffered from premature ejaculations. The first time I made out with a boy when I was sixteen, I had an orgasm from just him kissing me and dry humping me. Three days later when I gave the same boy my first blowjob, I had an orgasm from just sucking his cock. I didn’t have premature ejaculations anymore, but I do orgasm quickly.
As my cum splattered on the lounge chair, Derrick grunted out he was going to cum.
“Cum inside me, please cum inside me,” I pleaded. I enjoyed the feeling of a man cumming inside my “pussy.”
The boy did. He gave a series of loud grunting moans as I felt his cum shoot inside my ass. It felt so good.
My orgasm ended before he did, and after Derrick was finished, he pulled his cock out of my ass. I did not move and was panting and enjoying the euphoric feeling of my after-orgasm and just having my ass fucked.
Derrick got off the lounge chair and walked around to where my head was resting and stuck his cock in my face.
“Be a good whore and clean it off,” he told me.
Without hesitation, I lifted my head and started cleaning his cock. I licked it clean and then sucked it into my mouth and sucked it clean.
“You like tasting your pussy, don’t you?” he commented.
“Umm, yes,” I admitted.
Derrick laughed and called me a slut and told me he had to go but would come visit me again. He told me I was his whore now, and he planned on taking full advantage of me being his slut.
Derrick left me lying on my stomach, cum on my face, and Derrick’s cum was starting to leak out of my asshole. When the bliss of the after fuck wore off, I started to cry. I felt humiliated at what I had just done and allowed to be done to me. Worse, I felt shame that I enjoyed it and that it had turned me on.
After I cried for several more moments, I pulled my bikini bottoms back up, grabbed my top and towel, and ran into the house to take a shower. While I was in the shower, all I could think about was what Derrick and I had done.
Once again, the shame of it started to make me cry, but it also aroused me again. I tried to think of something else, but as I started to wash my private areas, my cock got hard again. I thought about the names the boy called me, how I begged him to make me cum and fuck me, and how wonderful it felt.
It was like a situation I could not win. The more I thought about how humiliated he made me feel, the more shame I felt but the more aroused I got as well.
I then started slowly stroking my penis slowly, then faster and harder as I slipped a finger into my ass. I jerked off in the shower while I finger fucked myself and thought about the cruel, ugly boy with the ugly cock debasing me, sucking his large cock, and fucking me. I jerked off until I had another orgasm and once again I felt the shame of it. Honest to God, I was crying from shame as I masturbated and had an orgasm. The orgasm was intense and felt great.
After the shower, I tried to keep my mind off of Derrick. I did some housework and then went for a long bike ride. It seemed to work. That was until I went to bed.
Lying in bed, I kept tossing and turning as I thought about that afternoon. I tried not to, but could not help it. Disgusted with myself and my thoughts, I took my six-and-a-half-inch, pink, vibrating dildo and lubricant from my nightstand and fucked myself, and masturbated once more until I had another orgasm.
As I masturbated, I tried to fantasize about something else. I tried to pretend it was my ex Tim fucking me, but Derrick kept coming into my fantasy.
While I fucked myself with the vibrating dildo and jerked my cock rapidly, I started calling out aloud.
“Oh God, fuck me, Derrick, fuck me with your large ugly cock!” I cried out. “Fuck me and make me your whore!” Just as Derrick did I used the derogatory term for a transgender before the word whore.
As in the shower, the orgasm I had was intense and powerful.
Once more I felt such shame that after I had another orgasm, I cried myself to sleep.
