How A Good Girl Was Turned Bad free porn video

My name is Tamara and I am a twenty-eight-year-old male to female transgender.  I won’t bore people with my background growing up and all that because the story I want to write starts when I was twenty-seven.  I will write a little about me because I was far from the girl you are about to read about and the images in my photo gallery on my profile will imply.  I was a good girl until I started my relationship with Justin.  I grew up in an upper-middle-class family, my mother is black and my father is white.  I knew I was supposed to be a girl ever since I was young and with the great support of my parents, I was able to start transition when I was sixteen and have been on hormones for years.  I live openly as a female and have for a long time. 

I am petite, genes I suppose since my mother is small and my father stands only five feet seven inches.  I am five four and my weight fluctuates between one ten to one hundred pounds.  I am cute I think and have been often told I am pretty by my friends, men I have dated, people I just met, or even strangers.  I have small A-cup breasts due to the hormones and no intention of getting implants or having my penis removed.  I liked my penis; it’s a lot of fun.  It’s average size but due to my small body, it looks larger.  Being kind of into a semi-punk style of clothes and look I had been dying my long black hair a bluish shade for years.

I am a rather prissy type of girl.  I like frilly clothes, nice shoes, manicures, and pedicures and I don’t do fake fingernails.  My voice is very feminine and not to put my trans sisters down, but it’s not at all like a lot of transgender girls I know.  The type of high feminine voice that has that hint of maleness to it that transgender females can achieve by voice training or surgery, but my voice is soft and sweet and feminine sounding.  I have always had a girl’s voice.  I was born with an abnormally small larynx and vocal folds. 

It was not known until I started to go through puberty and my voice never changed and I sounded like a pre-teen or teen girl.  It could have been fixed with easy surgery, but by then I knew I was a girl and I did not have the surgery.  With my voice, my petite stature, my feminine mannerisms, and my sexual attraction to males I thought it was God’s way of telling me He made a mistake with my gender.  As I entered adulthood my voice remained that of a female.  I have been told by many people I meet that they cannot believe I am transgender.  Not that I care what people think about my sexual gender. 

I have a great personality but I can be rather shy, always have been, and while I have friends I don’t have a lot of them due to my shyness.  I hate getting out of my comfort zone.  I am a nice girl in all aspects of my life.  I am kind, caring, sweet, and a good girl with a great sense of humor and very polite.  I was raised to say yes sir and no sir and yes ma’am and no ma’am.  I had always been a rule follower for as long as I could remember.  My parents would tell me to clean my room and I cleaned my room with no back talk, when I got older and started going out with friends I was always home at least fifteen minutes before curfew, and I never went through a rebellious stage.  As an adult, I was still that type of person. 

Not to say I was perfect and I had my faults as everyone does.  One of those faults is that I am not very authoritative and can be a pushover and people have always taken advantage of that.  I don’t blame them for it; it’s my fault because I allow them to.  I never really felt it was much of a fault or weakness until I was passed over for a supervisor job in the IT department and my manager was very candid about it and told me that was the reason I did not get the job.  I tried to change, but it never took.   

I also never had any luck at romance.  It was not that I was transgender or not attractive but I have a couple of problems or issues when it comes to relationships.  I only date white men or boys, not that I consider that a problem or issue.  I have nothing against men of other races, but it’s just who I am attracted to.  I fall in love too easily.  What few guys I have been with have seen me as just sex while I see them as relationship potential.  My other issue is that I end up doing whatever that person wants me to do to please them.  Even in a relationship, I am very easy to take advantage of.  You would think knowing that I could change, but so far I end up in my same pattern. 

I am a very affectionate person and sensual person and I do love sex.  I am not a cold or dispassionate lover at all.  I love to kiss, hold hands, cuddle, love long foreplay, and having sex.  I am a bottom-type girl, but I hate using that term to classify myself.  I do not like to top a male at all and have only penetrated two people in my life.  I masturbate often even when I am in a relationship and having sex.  I would not call myself a prude at all, but there are things I have never done before and the kinkiest thing I do and enjoy is having my butthole rimmed and rimming a man’s butthole.  One guy I dated in a semi-long term relationship, I never know how long a relationship should be to call it long term, liked me to fuck him in his butt on occasion. Other than those things, I was rather “vanilla” when it came to sex. 

I gave my first blow job to a boy I had a crush on in high school when I was sixteen and he was seventeen and gave him oral sex on several occasions.  That was all he wanted from me and after a while, he got bored with it or scared someone would find out and ended it.  I was heartbroken because I thought we were more than just that.  I did not do anything sexual with another boy until I was eighteen and it was just oral sex and just the one time.  He was someone I knew and again I was hoping for more but once again I misread the signals.  I did not lose my virginity until I was nineteen to a boy I was actually dating.  We dated for about eight months before he ended the relationship and told me he liked me but could never get serious with a transgender girl.  Between then and when my story starts I have only had three other sexual partners with two being a one-night thing. 

The first was another transgender girl who was a roommate I had in college.  I was a junior and she and the other transgender girl we shared an off-campus apartment with both worked and did not go to college.  I met them when I answered an ad off Craigslist about looking for a transgender roommate.  Aurora was a cute white girl, much taller than me, and had an athletic-toned body.   She had B-cup breast implants and would tease me about getting implants myself.  We were alone and getting drunk one night and having a self-pity party about how men sucked and why can’t we find love. 

One of us, I forget who, joked about we should become lesbians and one thing led to another and we had sex.  We had sex several times and it was the first time I ever penetrated someone with my penis.  She fucked me first and later that night I fucked her.  It felt very good of course, but I did discover I would much rather be the one getting penetrated.  The next morning we agreed to never let it happen again or discuss it and we didn’t.     

The next time was years later and with an older, married man I met in a club and I was drinking, we were dancing and I got horny and the alcohol and my sexual desire overwhelmed my judgment.  We went to a cheap motel and had sex just the one time.  After he fucked me and orgasmed he started to feel bad about having sex with a transgender girl, bad about touching my cock, and got homophobic like a lot of straight men get after they have sex with a transgender. 

At least that’s what my transgender friends told me happens often.  He quickly got dressed and left me in the hotel and I had to call Uber to get a ride back to my car.  I felt like a prostitute and cried on the way to my apartment I was living in at the time.  I cried because of the way he treated me when he was done fucking me and the fact he was married.  It bothered me he was married.    

My story starts when I was twenty-seven, had not had sex with a person in almost four years.  Yes, you read that right.  Almost four years since I had sex!  Not that I did not get asked out, I did often even when I told the person I was transgender.  I just did not find any of them interesting and some were black men I had no interest in dating.  I know I could have gone out and hooked up or now with Covid rampaging the world I could have gone on a transgender dating or hookup website.  As cute as I was and as petite as I was and as feminine as I was, I knew I could have been very selective in the men from a transgender dating site.  But that was not me or who I was.  I did not do random hookups or meet people just for sex.  I was still a good girl and even after my poor luck with relationships, I still believed in romance and love, not meeting some guy in a seedy motel room.

Being a sensual girl and having what I thought was a healthy and often overactive sex drive I just relied on my hands and the few sex toys I had to get myself off.  My story is how I got myself in a relationship with a then seventeen-year-old boy.  He is now eighteen and I am now twenty-eight and as much as I hate to admit it because of the age difference, I have fallen in love with him and fallen into my pattern of doing anything to try and please him. 

I am well aware that he takes advantage of that and to him, I am just a sex object for him to use and play with, but I can’t help how I feel and I allow it and while I did wish he loved me back I cannot deny the arousal and debase sexual pleasure I get from the things he does to me, what he has me do to him, and the things he has me do for him.  Things I never thought I would allow to be done to me or allow myself to do in a million years.   

I work as an IT person for a large international company based in Atlanta that is known worldwide that pays very well and is LBGTQ friendly.  I started with the company right out of college in the IT department.  I live in the Atlanta area and own a three-bedroom, two-bath house in a nice middle-class neighborhood.  My home has a pool surrounded by a privacy fence.  The pool was just a bonus.  I was not looking for a house with a pool since I can’t swim but the house I liked just had one.  I do use it and enjoy laying out by the pool and relaxing and do wade in the shallow end to cool off on hot summer days in Georgia.

Besides not dating anyone, my life was going great.  Work was going very well, I worked with a great IT team of eight who respected me and had no issue I was transgender.  We would go out to eat and have a few drinks after work on occasion.  Then Covid hit the world.  We were locked down in April.  Due to my job I was able to work from home.   At first, it was not much of an issue and we kept busy since we had to help set up company computers and systems in the homes of some of the employees who were now working from home; the sales reps, customer service, complaint department reps, and so forth.  I was shy and introverted at times and working from home was nice.  I lived in the Atlanta area and if I wanted anything I could pick up the phone or go online and have it delivered. 

Sex was not a problem because I was not having sex anyway so I just kept using my hand, my anal plug, my anal beads, and my penis-shaped dildo to get myself off.  I did look at Fleshlight masturbation toys online but thought they were much too bulky and saw they made another toy called a Fleshskin so I ordered that.  It is freaking great and when it arrived I used it four times the first night while fucking my ass with the penis-shaped dildo.

I was not afraid of Covid but did practice social distancing, wearing a mask, and washing my hands constantly, so I did get out of the house about once a week just to get out.  I would go to the grocery store or just drive around, but I was getting cabin fever.  The weather was warm and I was able to open my pool, although it took me weeks to get someone out to clean it and get it ready for the summer due to Covid, by the end of May I was able to lay out by the pool.

I was wearing a new bikini that I ordered online.  It was advertised as an African print, but it wasn’t really but I liked it.  I had my iPad with me and was going to read a book I downloaded.  I had a weakness for erotica stories.  This one was about three people, two men, and a woman shipped wrecked on an island inhabited by Polynesian shemales and futanari women.  I know, cheesy as everything but it looked sexy and had different kinks in it.  I figured I would lay out by the pool for a while, read and get aroused if the book was good, masturbate, take another shower, and fix dinner. 

“Hey, Tamara.  I knocked on the door but no one answered and thought you may be out here,” a male voice interrupted my reading.

I quickly grabbed my towel and placed it over my lap.  I was already well into the three hundred-page book and it was very erotic and hot.  The characters in the book did things I would never do; multiple partners, bondage, orgies, and other kinky things.  While I would never do such things in my life it was arousing to read about and my penis was hard.  I had also been idly rubbing it over my bikini bottom while reading.  Don’t judge me, I could not help it.  I had gotten horny reading the book.  I looked toward the gate to my backyard and saw Justin walking toward me.  He was wearing a white swimsuit, had his shirt off and holding it in his hand.  Damn, I forgot I told him he could use the pool anytime he wanted and had an open invitation.

Justin lived two houses down and across the street from my house and I am good friends with his mother and father.  I had known Justin for the past two years when I moved into the neighborhood.  Justin’s mother Julia and his father Frank had been the first and only ones in the neighborhood to welcome me when they bought a cake over when I moved in. 

Other neighbors did not welcome me not because I was black or transgender, which at the time they did not know and some still don’t; but because things like that are not done anymore by most people.  I am friendly with all my neighbors and them with me, but I became very good friends with Julia and Frank.  Both of them and I suspected their son Justin know I am transgender.  The cake Julia baked sucked and we shared a laugh when the day I met them when I offered to cut them a slice and Frank declined and told me the cake was going to taste like shit because his wife could not cook. 

“What are you reading?”  Justine asked as he now stood over me.

I quickly closed the story and blushed. “Just… Just a book… A mystery novel,”  I lied.

I looked up at Justin and he smiled.  Justin was seventeen and brilliant.  I don’t mean just smart, but genius-level IQ brilliant.  He skipped the ninth grade in school and went into high school and at seventeen was a senior and about to graduate.  He had a full academic scholarship to Georgia Tech in Atlanta but was offered full scholarships from many other schools including prestigious Ivey League schools.  He chose Tech because it was close to home I guess.  I never asked.   Justin was sometimes difficult to talk to because he was so smart.  Hell, at seventeen he knew a ton more about computers than I did and I thought I was pretty damn intelligent when it came to computers.  But he was no nerd and did not look like one either.

Justin was six feet tall, naturally well built with a swimmer-type body.  You could see his muscles hiding under his skin and if he worked out the boy could easily have a nice muscular-toned body, but he still had very little body fat on him.  He was one of those white people who had a natural light tan body that would bronze so well in the summer just like his father.  Justin had sandy blonde hair that he wore cut and styled just past his ears and his long bangs swept down to the right of his forehead.  I called his hair cute an emo style, but Justin would call it a skater style.  Justin was into skateboarding and hung around with a skater crowd. 

His eyes were a sky blue color just like his mother’s.  He had the beginnings of chest hair on his chest.  It formed a small spot in the center of his chest and a line of the hair ran down to his belly button.  It was a shade darker than the hair on his head and looked fine and soft.  I would not say Justin was super good-looking or movie-star handsome or even ruggedly handsome, but he was very cute and from knowing him for the past three years I knew he had no problem getting girls to date him.

Justin was very outgoing, had a great personality and from being very good friends with his mother I knew Justin was rather a bad boy type.  Not that he did anything criminal or anything that would get him in trouble with the police, but he was sort of rebellious and liked to push the limits of his parent’s authority.  I suspected Justin did do some criminal activities but just was too intelligent to get caught.  He was both book smart and street smart. 

His mother blamed the peer group he was friends with but I did not agree with her.  Justin was a leader, not a follower and if anything he influenced his peers, not the other way around.  He could also be rather arrogant and sometimes could be just a downright asshole.  For about the past year he flirted with me and I had to admit I would mildly flirt back, but to me, it was just harmless and making comments like, “only if you were older”.  Of course, I would never do anything with Justin.  I was ten years older than him and considered his mother a dear friend. 

Since Justin was now closer to me I could see he was not wearing a bathing suit at all, but a pair of white shorts and besides the tee-shirt, he was holding his cell phone in his hand.  On his feet was a pair of Vans skateboarding shoes and no socks. 

“Is the book good?”  Justin asked. 

I blushed as I reached over and grabbed my sunglasses off the small table next to my pool lounge chair and put them on.  I blushed because Justin’s eyes moved up and down my body.  I had no idea why he looked at my chest like he did.  Laying on the chair I was about flat-chested and had zero cleavage. 

“It’s ok.”

Justin sat down in the chair next to mine.  “What’s it about?”

“Just, well, just about a group of people shipwrecked and a murder happens and how everyone suspects everyone else.  Typical mystery,” I lied.

“Ah.  I hope you don’t mind that I came over for a swim.  You did tell me I could come over anytime even when you were not home.”  The way he said it sounded like he did not care if I minded or not.

“No, it’s fine.”  Again I lied.  I did not mind him coming over uninvited because I did give him an open invitation to use my pool.  What I minded was he came over when I was aroused and had an erection I was desperately trying to hide from him.

Justin stood up and placed his tee-shirt and cell phone on the chair and kicked off his shoes and walked to the edge of the pool and dove into the deep end.  I was going to get up while he was underwater and walk quickly into the house but Justin came above the water and held himself afloat by the edge of the pool before I had time.  As he started talking to me I was mentally willing my erection to go down but it wouldn’t. 

Justin talked about how Covid sucked, about how he hated they canceled his high school graduation, how he hoped by the fall schools would be open and he could go to Tech and not have to do online classes, and other inconsequential topics.  He asked about me and how I was doing but mostly talked about himself.  Like I mentioned, Justin was very arrogant.     

Go down, go down, go down!  I screamed in my head to my penis but it was not working.  I could not get rid of my erection and if I was honest with myself, Justin was not helping.  He was very cute and I had always been attracted to arrogant men or in his case boy.  Not that I would do anything with Justin.  He was too young and my friend’s son to boot and I don’t just jump into bed with a guy anyway.  I just needed him to go underwater so I could get up and cover my erection and get in the house so he won’t see it.

I picked up my iPad and saw it was almost one in the afternoon and I had an excuse to go into the house only if Justin would stop looking at me.

“It’s about time for me to fix lunch, Justin,” I told him hoping he would stop talking to me and go back to swimming.

“That’s cool. I haven’t eaten either so maybe I can join you.” Justin then lifted himself out of the pool.

The first thing I noticed was he was not wearing any underwear and his now wet, white shorts were transparent.  The next thing I noticed was he had an erection and unlike me, he was doing nothing to hide it.  The last thing I noticed before I adverted my eyes was how big his penis was.  That surprised me.  It didn’t surprise me that he was large because he was white, one of the men I had dated for a short period of time was very well endowed and he was white.  It just surprised me because I was not expecting it from a seventeen-year-old boy I guess. 

I turned my head to look away as Justin walked to me but I cut my eyes to look at his visible penis and thankfully Justin could not see I was looking because of my sunglasses.  I tried to look away but I could not help it.  It had been a very long time since I had seen a real penis besides my own.  Now my cock was very hard.  The achy erection you can get for being very aroused and erect for so long and needing relief.  I could feel it pressing against my bikini bottom, straining to be released and aching to be touched, to be pleasured, and to be given that blissful relief of orgasm. 

Justin now stood over me and I could have sworn in a court of law that he posed his body so that I would see his large, erect, visible, penis.  He was standing over the middle of my wooden Chaise lounge chair; so close that water dripped off his body and fell on my thighs and knees.  I didn’t even move because my eyes were so focused on his hard cock.  I knew I should not have been looking and I tried to look away and my mind screamed to look away but I didn’t. 

“I forgot a towel,” Justin said.  “Mind if I use yours?”

Before I could say no or even react, Justin grabbed my towel off my lap.  I made a girlish eking squeal and instinctually brought my hands down to my crotch to cover my erection.  My hands didn’t make it.  Justin grabbed them and held them by my wrists with one hand.  I tried to twist my hands free but Justin held them tight as he dried his hair and face with the towel.

“Seems we both have the same problem,” Justin teased and threw the towel on the ground.

“I… What... I don’t know what you mean,” I stammered out.

Justin let go of my wrists and sat down on the lounge chair even with my midsection.  My pool furniture was plush, expensive, and very roomy.  The lounge chair was oversized and with my petite body Justin could have laid down next to me with plenty of room.  I placed my hands by my sides and drew my knees up and placed my feet flat on the cushion of the chair and turned my lower body slightly away from the boy. 

“Yes, you do. You know exactly what I mean,” he grinned at me.  “We can help each other out.”

I was frozen by his bold and implied suggestion.  My mouth was dry and I found I could not speak.  Justin placed a hand on my upper thigh and lowered my legs back down flat and even spread them apart slightly.  I couldn’t move.  It was like one of those nightmares you have when the monster is chasing you and your body is frozen.  As much as your mind tries to will your body to move, you can’t. 

My mind was screaming at my muscles to move but they wouldn’t.  I was not afraid, I just couldn’t move.  Justin leaned down to my face and raised his other hand to my cheeks.  I actually pursed my lips, God help me, I did!  I thought he was going to kiss me and my body acted on its own accord and readied itself to kiss him back.  I told myself not to but my body once again would not obey.

Justine grinned at my obvious willingness to have him kiss me and took off my sunglasses, folded them closed, straightened back up, and placed them on the ground on top of the towel.

“You have such a pretty face and your sunglasses hide it,” he told me and I felt his hand run a little further up my thigh.

“Justin, you need to leave now,” I told him but there was no conviction in my tone.  No authority for him to obey me.  No movement of my body to push him away or get myself up off the chair.

Maybe it was my lack of pushing him away, my lack of not getting up myself and going into my house, or my lack of telling him to take his hand off my thigh that encouraged his boldness.  I don’t know what it was or what I lacked or did not do that gave Justin the audacity of his next move, but it had to be something I did or did not do.  Justin placed his other hand on my bare stomach and lightly ran his fingertips over my skin.  There was a slight tickle from his caress, but damn it felt nice and sensual.  A whimpering moan escaped my mouth.

“I have known you for what, two years?” Justin asked and I nodded.  His fingers kept running over my stomach and now he started moving his hand gently up and down my thigh.  I just laid there.  “You know, I did not know you were a tranny for the first year I knew you?  All the times you came over to the house to visit mom or to my dad’s cookouts and their parties I had no idea. Who would?  You are so pretty and sexy.  I had a crush on you from the first time I saw you.” 

I swallowed hard.  I knew I should have got up and run.  I knew what he was doing was wrong.  I knew that my not moving was wrong. But I didn’t. I listened to his confession and had to admit his caresses on my stomach and thigh felt very nice.  My cock felt like it was going to explode with just the lightest touch.

“It was my dad’s Labor Day cookout,” Justin continued, “when I first saw you.  You were wearing a light blue sundress with white polka dots but what I liked was that you were wearing blue Converse high tops and white socks with blue stripes and how it matched your hair.  I thought you looked so pretty and sexy and thought from your outfit that this girl must be so cool.”  I let out another involuntary whimper of pleasure as Justin’s hand on my thigh moved up to my inner thigh near my hard penis.  The entire time he was talking I kept watching his fingers trace over my stomach.

“I had never been attracted to a black girl before until I saw you that day.  So small and petite and how polite and friendly you were to everyone and how your laugh was so musical. I even got jealous when Mr. and Mrs. Williams’s son flirted with you and you flirted back.  Do you think he suspected you were a tranny?  I don’t. No one would have.”

Mrs. And Mrs. Williams lived in the neighborhood and were one of the few black families that did.  Their son Andre was around my age and he did indeed flirt with me.  I suspected because I was the only black girl our age there. 

I looked up and looked Justin in the eyes, “I… I didn’t mean anything by it.  My flirting.  I was just being nice.”  I finally found my voice.  I had no idea why I felt I needed to justify my actions to Justin.  It was none of his business who I flirted with! 

“Did he ask you out on a date?” Justin asked; his fingers still tracing over my body.

“Yes.  He called me the next day.  I didn’t go out with him.  He is not my type,” I admitted.

“Why?  Were you afraid he would find out about you?”

“No. I would have told him.  I don’t trick guys like that.  Never have.  Also, I don’t hide who I am but I don’t advertise it either.  Someone knows then they know.”  God his fingers felt so good on my stomach and thighs!  I needed him to leave.  I needed to go into my house and jerk off.  I needed the wonderful physical relief of an orgasm so bad.  “I… I didn’t go out with him because I don’t date black men,”  I confessed.

Justin smiled, “Good to know.  I found out you were transgender about a year later when I overheard Mrs. Habersham mention it to my mother.  She was rather upset by it; Mrs. Habersham was not my mother.  My parents already knew and my mother was rather angry at Mrs. Habersham and told her off as she defended you.”

Mrs. Habersham was my next-door neighbor.  She was in her seventies.  I don’t know if she was more upset about having a transgender girl for a neighbor or a black girl for a neighbor.  Regardless I am still very nice to her and she is very nice to me to my face.  Of course, I don’t agree with her slight racist attitude and the fact she thinks I am a perverted person for being transgender, but honestly, I can understand her.  I can understand her views on me because of her age and the time she grew up in.  Older people like her, I just ignore their prejudices and lack of understanding.  It’s the younger people who have those beliefs that make me angry.

Justin’s fingers caressing my stomach moved higher up and he started tracing his fingertips up and down; up to my bikini top and back down to my stomach.  I knew my nipples were erect; I could feel their tautness.  When I looked down at his fingers I saw they were poking out under my bikini top.  I blushed when Justice’s looked at them also.  Still, I felt frozen and was enjoying his touch.  I knew I should not be but I was.  I had not been touched like that for a long time. 

“At… At least knowing I am transgender stopped your crush on me,” I said.  I was hoping that was true, but what the boy was doing to me I knew it wasn’t.  “What young white boy wants to have a crush on a black transgender girl?  His friends would think he was a pervert and tease him relentlessly,” I added hoping to deflect his attraction to me.   

Justin chuckled, “Quite the contrary, Tamara.  I found it sexy.  Yes, it surprised me also.  But I found it erotic and I was turned on about it.  I would masturbate thinking of you; you’re small body, your small breasts, and what your cock looked like.  I would get off imagining you giving me a blow job and then fucking your tight, little, black ass.  Thinking of you jerking your cock and seeing it shoot its cum when you orgasmed.  I even started watching tranny and shemale porn.  Hell, I even started going to websites that catered to men who were dating trannys.  Looking at the bulletin boards, the forums, joining in the chat rooms, and learning all I could about it.”

“Justin, that’s enough,” I said and tried to sound harsh.  Maybe it was how he admitted what he thought about doing to me as he masturbated and his crudeness in the way he admitted it, but whatever it was I knew this had to stop.  “Frist I don’t like the term tranny or shemale.  I find it offensive and if you did all you said you did about learning about how to date and treat transgenders like you said then you would know better.  Second, this is going to stop now.  Ok, sure I am flattered and yes it felt nice because I have not dated anyone in a long time and I liked the attention.  I let it go too far and for that I am sorry.  It’s my fault.  I should have stopped it sooner.”

Justin laughed, he actually laughed at me!  I know why he did.  I tried to sound harsh and authoritative, but I didn’t.  My voice sounded like it was pleading.  I sounded more like I was begging and not harsh or commanding at all.

“Don’t laugh, Justin.  I am sorry you think you are in love with me.  You really aren’t.  Maybe, well, umm, maybe it’s that since you found out I was transgender that it’s something new to you,” I tried to play amateur therapist.  “I am sorry I made you feel that way.  I am sorry I let this happen.”  I had no clue why I was apologizing but that was me.  I always apologized for things that were not my fault.

Justin laughed harder at me.  “Love you?  Let’s not get carried away, Tamara.  I never said I was in love with you.  I said I had a crush on you and yes you being a tranny girl opened up a new world for me and I admit I find that world sexy and I find you sexy, but no I am not in love with you.”  Justin still ran his fingertips over my body and I still let him. 

He sounded like he was lecturing me.  His entire talk to me sounded as if he was lecturing me.  It was nothing new.  That was how the boy communicated.  He sounded as if he was talking down to me, but he talked to everyone that way including his parents.  In normal conversation, Justin used words that one would only find on an SAT exam.  I once confessed to his mother that after a conversation with Justin I had to use my phone and google the definition of some of the words he used.  His mother laughed and said she had to do the same thing sometimes.  Justin was used to being the smartest person in the room. 

“Let’s call it a crush or lust,” Justin continued his speech.  “Maybe an infatuation but certainly not love.  I told you we can help one another out.  Your cock is hard so I know you are horny.  It’s been hard since I came into the backyard.  I am horny and I want you.  I have always thought you were very pretty and incredibly sexy and when I found out you were transgender I wanted you even more.  I know you are not dating anyone to help you with your sexual need and…”

“How do you know that?”  I asked defensively.  “Maybe I am seeing someone.  You don’t know,”  I lied.  “What do you do?  Stalk me?”  I then cried with pain.  “That hurt,” I whined.  Justin had pinched my inner thigh very hard and damn it did hurt.

“Don’t interrupt me anymore,” the boy told me.  “No, I don’t stalk you.  I know you're not dating anyone because you already said you have not dated anyone in a long time.  Also, I know you are not because last week when you came over to talk to my mother and had too much wine you mentioned to her that you had not had a relationship in years or had sex in years.”

“Oh,” was my only reply.  He was right; I did confess that to his mother after being tipsy.

“We are going to help one another.  I am going to get you off and in return, you are going to get me off,” Justin told me.  He did not ask, he did not suggest it, and he did not try and seduce me.  He just bluntly told me what we were going to do.

“I… I don’t think so,” I muttered and then took a deep breath to try and get some type of control over the situation.  “Justin, you need to stop now.  What you want to happen is just not going to happen.  You are only seventeen and I am twenty-seven and if you don’t stop I will tell your parents.  I think you should leave now.”  I took another deep breath. “Don’t you have a girlfriend who can take care of your umm, needs anyway?”

I should have felt more confident in telling Justin no, but I didn’t.  Once again there was no conviction or confidence in my voice and once again Justin laughed at me.  “Yes I do and she does a fine job with it but who takes care of your needs?  Aren’t you tired of jerking yourself off?”

For some reason, I felt jealous Justin admitted he was having sex with his girlfriend.  I had met Kathy a few times at his parent’s social gatherings and she was a sweet, pretty girl who I never even considered being jealous of until that moment. 

“That… That is none of your business.” I blushed at the thought of him assuming I masturbated.  “This is going way too far, Justin.  You really should leave and I promise I won’t say anything to your mother.”  I had hoped by invoking the mother card Justin would stop.  He didn’t.     

Justin’s reply was to run his fingers that were caressing my chest and stomach down past my belly button, my pelvis, and then he slipped them under the waist of my bikini bottom.  At the same time, he slid his other hand up my inner thigh, brushed my erect penis which caused me to make a gasp of pleasure and whimper, and then he slid the fingers of that hand under the waist of my bikini bottom.

“Justin, please… Please don’t,” I whimpered.  I then did a strange thing and I don’t know why I did it or maybe I knew why and just did not want to admit the reason to myself.  When I pleaded for Justin to not remove my bikini bottom I moved my body flat on the lounge chair and spread my legs slightly apart.  The new position allowed Justin to remove my bottom easier.

“Hush, Tamara, I just want to see your cock and to touch it,” Justin told me.  I would say that when I moved my body for him it encouraged him more and gave him more confidence in what he was about to do, but Justin did not need more confidence. 

I closed my eyes and took a deep breath as Justin slid my bikini bottom down. “No, please,” I begged again.  Even though I told him no I put my feet flat on the lounge chair and lifted my butt to allow the bottom to slide off easily.  Justin pulled them down to the top of my knees and my hard cock sprang up.  Having it exposed in front of the seventeen-year-old boy and allowing him to see it embarrassed me.  I tried to cover myself with my hands, but Justin grabbed my wrists again and lifted my arms above my head.

“That’s sexy, Tamara, seeing your hard cock on your feminine figure,” Justin told me.  He was still holding my arms. 

I tried to cross my legs at the thighs and turn my body to hopefully hide myself from his stare, but Justin used his other hand to prevent me and spread my legs apart.  I didn’t beg for him to stop.  I didn’t say a word.  I just blushed and whimpered.  Justin let go of my legs and I flinched when he used the back of his hand to glide up my shaft and made a whimpering moan when it touched the head of my cock.  I flinched and made the same whimpering moan when the boy ran the front of his hand touched the other side of the head of my cock and down my shaft. 

“Felt good, didn’t it?  Feels good to have someone else touch your cock for a change doesn’t it?”  Justin taunted me.  I just stared at his hand as he repeated running the back of it up my penis and the front of his hand down my penis.  It did feel good.  It felt damn good.  I could not seem to take my eyes off of Justin’s hand gliding up and down my penis and watched as the boy’s hand close around my hard cock causing me to whimper in pleasure.

“It looks bigger than it really is,” Justin told me.  His hands were larger than mine of course and while he had large hands compared to mine they were average size for a man of his stature and his hand covered almost my entire shaft just below the head of my cock.

Justin was right, I have an average size penis when fully erect, about six and a half to almost seven inches, but because I am petite and that it’s hairless it looks larger than it is.  When I am flaccid my penis shrinks to be very small.  That is great for me when I am in my bikini or just panties because you can’t tell I have a penis when it is flaccid.

Justin started to glide his hand up and down my shaft slowly, putting very little pressure on my cock.  I watched as his hand went up and down and made these soft whimpering sounds of pleasure I always make when my cock is being played with and caressed so gently.  Justin let go of my arms and I kept them above my head as I watched him caress my cock.  He had me now and he knew it.  The pleasure I was feeling was too great to make him stop now.  I did nothing to stop him when he lifted my bikini top to expose my small breasts and erect nipples.

“You have such small, sexy tits,” Justin told me as he played with me.  “Your nipples are so dark and perfect size for the size of your breasts.” 

Justin ran his other hand up my stomach and over my breasts and I let out a moan of pleasure when the boy took his thumb and forefinger and rolled my hard, left nipple between them.  Justin ran his hand to my right breasts and again I moaned when he took that nipple between his fingers. 

“Your nipples are rock hard, Tamara,” Justin teased and I gave a louder moaning cry when he pinched my nipple hard.  It felt good.  I liked my nipple played with and pinched like that. 

As Justin pinched my nipples, going back and forth to each one, his hand on my cock tightened its’ grip and he started jerking my cock harder and faster.  I started moaning louder from the pleasure he was giving me.  I was a very affectionate, sexual, and sensual person in an intimate relationship and highly enjoyed sex and all kinds of sexual physical contact.  I enjoyed masturbating myself, but having someone else do it to me was so much better!  I had almost forgotten how great it felt to have someone else jerk me off.      

“Oh, God… Ohhh… Uhhh… Justin… Ohhh, my God, that feels so good!”  I cried out as he worked my cock and nipples with his hand and fingers. 

I have always orgasmed rather quickly when I masturbate, have a guy masturbate me, having my cock sucked, and even quicker when I have my cock jerked when I am getting fucked.  Normally I will orgasm in about five to seven minutes at the most.  But that day with Justin jerking my penis and pinching my nipples I lasted all of about a minute and a half tops.  

“Oh, God… Ohhh, baby… Uhhh… Justin, I… I am going to cum!”  I moaned out very loudly.  “Ohhh, God… Please… Please don’t stop!  Oh fuck I’m cumming... Uhh… Ohhh… God… Uhhh fuuuck… Uhhhgh!” 

At the time I did not care due to my pleasure, but later when I thought about it I hoped Mrs. Habersham was not in her back yard working in her garden because surely she would have heard me as loud as I was moaning and screamed out I was about to orgasm.  I was always very loud when I was having sex.

My body jerked and spasm as Justin kept stroking my cock hard and fast and I moaned and grunted and shouted to God and Justin as I orgasmed.  My thick, milky white sex fluid exploded out of my cock and the first load of it shot up far and splashed all over my chest and some actually landed on my chin.  Justin kept jerking me and I kept moaning as I kept cumming.  I was no longer shouting any words because the blissful relief of my orgasm was so intense I could not form words.  The cum now sprayed out of my cock in an erratic spray and splashed over my stomach, my pelvis area, my upper thighs, on the lounge chair, and as Justin milked my cock for every last drop of cum my fluid leaked over his hand.  My orgasm was intense and wonderful and my cock expelled a large amount of the sticky, warm liquid. 

“Stop, please, Justin, please stop now,” I gasped out as Justin kept jerking my penis until it became very sensitive.  He stopped. I lay in the lounge chair with my eyes shut and panting for air as my chest was rising and falling, my stomach muscles twitching, and my legs were shaking.

“That was fucking great,” Justin told me and I opened my eyes and looked up at him.  “You came so fucking hard and so much and so fast.”

“I am sorry,” I apologized for no reason and Justin chuckled.

“Don’t be.  That was incredible seeing you cum.  I liked seeing my first tranny shoot her cum all over the place.”  Justin grinned at me.“My first shemale and my first black girl all in one.”

Justin brought his hand to my mouth and I started licking his hand and fingers clean and then I scooped up as much cum off my body as I could and licked my fingers and hand.  I loved the taste of cum whether it was mine or that of another man.  I looked Justin in the eyes and licked his fingers and hand and licked my own and ate my cum in a sensual manner.  I knew how to be sexy when I wanted to be and the way the boy looked back at me I knew he liked what he saw.  After I could get no more cum from my fingers, Justin picked up my towel and handed it to me.  I wiped myself off, pulled my bikini top-down, and my bottoms up. 

Justin stood back up and his shorts were still damp and I could still see his penis through the thin, white cotton material.  I reached up with my left hand and ran my fingers down his stomach and then over his hard cock.  I was still amazed he was so large.  I don’t know why it surprised me he was.  I was just not expecting it.    

“Do you want to lie down next to me while I jerk you off?”  I asked Justin in an enticing tone as I continued to rub his cock through his shorts.  I wanted him to lie down and I wanted to kiss him and suck his nipple as I jerked him off.

Justin ran his hand caressingly over my cheek. “Jerk me off?  No, Tamara, you are going to suck my cock not just give me a lousy hand job and I’m going to cum in your sexy black mouth,”  Justin told me. 

I did not hesitate or protest and sat upon the edge of the chair as Justin unbuttoned his shorts and pulled them down.  I wanted to suck his cock.  I wanted to feel it in my mouth.   Wanted to feel him shoot his cum in my mouth and taste it.  I knew it was wrong for several reasons, but after what I just allowed him to do to me and how good it felt I had the need and desire to pay him back in kind.  I looked at Justin's hard cock and swallowed audibly.  He was even larger than I had thought seeing his penis under his shorts.  He had to be eight and a half inches as I thought but it was his girth that I did not get a good judgment of until I saw his naked cock.  He was thicker than I had previously thought.  I took his cock in my hand. 

“It’s so big, Justin.  I have not done this in a long time so please be patient,” I said in a tone more whiney than I intended.  I had not had a real penis in my mouth since forever.  The only thing I had sucked the past four years was my penis-shaped dildo and it was only six inches long and not near as thick as Justin’s penis.

Justin reached down and caressed my face and then moved his hand to the back of my head.  “I am sure you will do a fine job,” he assured me and nudged my head to his hard penis.  “I am horny and need to cum so don’t tease me with your tongue.  You can do that another time.  Just put my cock in that sexy black mouth.” 

I didn’t bother mentioning there would be no other time and this was a one-time thing.  I could tell him that later.  I parted my lips and took Justin in my mouth.  I had to stretch my mouth open wide to accommodate him but I did fit him in my mouth.  Lucky I had a wide mouth which gave me a great smile and also helped giving blow jobs.

I loved sucking cock!  I know that sounded blunt but it’s just a fact; I love sucking cock and I was damn good at it if I do say so myself.  I loved the way a man’s penis felt in my mouth, down my throat, my whimpering sounds as I sucked him, his masculine moans of pleasure, and when he would spray his cum in my mouth.  I knew girls who said they did not enjoy it as much or married women who would say one of the best things about being married they did not have to give blow jobs anymore.  Not me.  I intended to suck my man’s cock all the time. 

I did as Justin told me to and did not tease his cock with my mouth or tongue even though I wanted to.  I started slow and when I took him deeper down my throat I gagged a few times until I found the right spot of how far I could go without choking.  On an average-sized penis, I was very good at deep throating the man, but Justin’s penis was too long.  Maybe if it had not been so long since I gave a blow job I would be able to deep throat the boy or maybe if he allowed me to take my time I could, but at that moment I did not try.

I could hear my whimpers and Justin’s occasional grunting moans of pleasure as I started bobbing my head back and forth faster and sucking harder.  He had his hand rested on the back of my head but was not forcing me down, just resting it there and allowing me to control the tempo.  Soon his shaft became slick with my saliva and I started jerking his cock in rhythm of my mouth. 

“Fuck, girl, you suck a good dick,” Justin told me.  “Like riding a bicycle isn’t it?”  He teased me.

I did not answer what I knew as a rhetorical question and kept sucking his cock and looked up at him.  I was highly enjoying myself.  I had to take my mouth off his penis a few times to catch my breath.  I would look up at Justin and smile while I kept jerking his now slick shaft and then once I caught my breath I would put my mouth back on him and once again bob my head back and forth as I gave him a blow job. 

“Fuck, Tamara, I’m going to cum… Fuck, keep going.  Uhhhgh… Don’t stop,” Justin grunted out.

I could feel his body tighten and Justin held my head tighter to him and started thrusting his hips forward, forcing his cock deeper down my throat.  I gagged a few times and a gob of thick saliva poured out of my mouth.  I started using both my hands to jerk his shaft and Justin gave one hard thrust and made a series of grunting moans as his cock exploded its cum into my mouth.  I gulped and swallowed all of it as I milked his cock for more.  I loved the taste, smell, and texture of his orgasm fluid.

When he was finished, Justin told me I gave a great blow job and pulled up his shorts.  I wiped my mouth with the towel.  He then picked up his cell phone and told me he wanted to take some photos of me.  Now I don’t like my picture taken because I can be rather shy about things and I never did selfies and I thought it was rather silly he wanted to, but I let him. 

He started just normal pictures and then told me to pull up my top and show my breasts.  I protested but he promised he was not going to show anyone.  I let him.  He took a series of photos of me and it was not long before I found myself naked and posing in ways that exposed all of me.  I did find it arousing and my penis became erect again, which Justin seemed to like as he took more pics of me with an erection.  When he wanted me to bend over and spread my ass apart I again protested.

“Don’t be such a prude, Tamara.  I won’t show anyone, I promise.  Besides, soon I am going to be balls deep in that sexy black tranny asshole anyway.”  Justin used his arrogant and commanding tone and I allowed myself to be photographed.  Little did I know that was just the start of many photos he was to take of me posing in various positions for him. 

“That’s great, Tamara.  Now put your bikini back on.  I think earlier you said something about making lunch.  I’m hungry.”  Justin then walked into my home through the sliding glass doors as I got dressed. 

I did not follow Justin immediately but stood by my pool stunned and thinking of all that had happened.  How he jerked me off, how I gave him a blow job, the pictures he took of me, and his arrogant assumption he was going to have sex with me.  I picked up the towel and my iPad and marched into my house with a purpose as I mentally prepared a speech.  I was going to send him home and tell him this was not going to happen again!  There were no ifs, ands, or buts about it!  Little did I know that when I walked through my sliding glass doors into my home my life was going to change.  Little did I know I would soon be doing things I never thought a good girl like me would do in a million years.