The photos in my photo albums titled My Pool are the actual photos Justin took of me by the pool mentioned in this chapter and the previous chapter.
When I walked into my house, I found Justin standing in my kitchen looking in my refrigerator. It annoyed me that he was making himself so comfortable in my house. At least he had put on his tee-shirt and the erection I had from Justin taking the dirty photos of me was gone. I was glad about that but highly embarrassed I allowed him to take them. I added that he is going to delete them to my mentally prepared speech. I was holding the cum stained towel and my iPad.
“Justin, we need to talk,” I told him after I cleared my throat, and put the towel and iPad on the kitchen counter. I was nervous and fidgeting and wringing my hands. I leaned against the kitchen counter opposite him.
Justin turned around and let the door to the refrigerator close. “You have nothing to eat.”
“I have plenty to eat. I went to the grocery store yesterday.”
“I didn’t see anything,” Justin sighed.
I then knew what he was talking about. I had plenty of food in the house but I was mostly a vegetarian and had no sandwich meat or any meat but fish. I did eat fish and other seafood and on occasion, I would eat meat. Thanksgiving I would eat some turkey or about once every two or three months I would crave a steak or a good hamburger. I never ate pork though.
“I can make you a veggie burger?” I suggested. The long speech I prepared in my head to tell Justin that he should leave vanished from my mind due to my need to please. My need to please was not just limited to Justin, I had this need to please anyone, to be liked by people I meet. Right then I wanted to please Justin in something as simple as feeding him lunch.
“I can order something?” I suggested. “I can get it delivered or go pick it up?”
Justin walked to me and I flinched when he stood in front of me and he leaned down. Once again I thought he was going to kiss me and once again I pursed my lips and tilted my head up to accept his kiss and once again he did not kiss me.
Justin chuckled in amusement at my expense and leaned closer and moved his head so that his lips were close to my ear. “Yeah, I would like that,” he whispered in my ear and I flinched again. Justin stood back up straight with his body almost touching mine. I tried to back up further but there was nowhere to go. “Order from Baldino’s. They deliver by Grubhub.” Baldino’s was a franchise deli not far from our neighborhood and they had very good food.
“O…Ok,” I stammered and said in a husky voice. I cleared my throat, “What do you want?” I asked as I picked up my iPad.
Justin moved next to me and sat on the counter close to me. He then leaned down and put his head over my shoulder. So close I could smell the chlorine from my pool in his hair. His bare leg touched my bare side. I felt my penis stir to life and mentally begged it not to get hard.
“Open the menu and let’s see what they have,” Justin said and I could feel his warm breath on my neck.
No, no, no! Please not now! I screamed in my head at my penis as I opened the restaurant menu. I could feel my penis growing. Justin put his head on my shoulder as he looked at the menu on my iPad. My breathing became harder.
“Order me the Italian sub. No onions,” the boy said. “And no onions on whatever you get.”
“But I like onions on my salad,” I replied and turned my head and Justin’s face was only about an inch from mine and I felt suddenly dizzy. “I…I umm,” then I realized why he said no onions. He assumed he would be kissing me.
Maybe I wanted him to but I wanted a lot of things that were never going to happen. I should have ordered inions just out of spite but I didn’t. I ordered my salad without onions. I paid for the order on my saved debit card and added the tip. I always added the tip on meals delivered on my card. I felt I got better service that way, when the delivery person already knew how much his tip was or that he was getting one. I was a very good tipper.
“No, use the option for them to wait until you come to the door,” Justin told me as I was about to click the button for the delivery person to just knock and leave the order on at the front door. Covid has changed things. I did. Justin hoped down off the kitchen
“It will take about forty-five minutes. I hope that is okay.”
“Yeah, that is fine. I am not that hungry anyway,” Justin replied and got off the counter. “We can go watch some TV and talk well we wait.” His eyes roamed up and down my body.
I moved the iPad over my crotch to cover my now semi-erect penis. It was just a small bulge in my bikini bottoms but noticeable. Waiting forty-five minutes may have been fine with Justin, but I was rather hungry. I could have made myself something to eat since I had plenty of food in my house I was happy with, but I thought it was rude to eat in front of someone who was not eating also. Plus, forty-five minutes was a long time to wait and be alone with the boy. I wanted him to leave. What I wanted to do was have Justin leave and continue reading my erotic fiction book and get myself off because I was sexually aroused again.
“I need to change and get a towel out of the guest bathroom to put down before you sit. Your shorts are still damp.”
“Yes, dear,” Justin answered in a mocking tone and it made me giggle.
I went into my bedroom and changed. I put on a pair of pink cotton brief panties with a black waistband and the word Spider-Man across the front on the waistband and an image of Spider-Man’s face on the seat of the panties. I had frilly, lacey, satin, or other style panties that were sexier, but I did not wear them often. I went mostly for comfort in a casual, everyday setting and I had a thing for comic book characters on them. Weird I know, but was my thing just as I like to dress semi-punkish attire I would throw together. It was my style I started in high school for myself and never changed it. I felt I was already unique in a way being transgender so why not become more unique in my choice of clothes.
I had other styles of course; sundresses, cocktail dresses, jeans, clubbing outfits, and other styles of clothes including a couple of evening gowns. For everyday casual, I went with what I felt was comfortable. I put on a black strapless bra and a pair of fluorescent pink running shorts. They were short up my leg but baggy around my crotch so my erection would not be too noticeable. I mentally tried to will my penis to go soft, which didn’t work, and put on a black tee-shirt that was a faux vintage concert tee with a Blondie logo on it. Feeling better that I was not as revealing I walked into my living room and found Justin sitting on the recliner, holding the remote to my TV, and flipping through the channels. He did get a towel from the bathroom and put it on the seat of the recliner. He had gotten two towels.
In my living room, I had the recliner, where I usually sat, a sofa, and a love seat that all matched and were nice plush leather. Justin watched me as I walked to the sofa and sat down on the edge with my feet crossed at the ankles, my keens pressed together, and my hands folded in my lap. I was once again twisting and wringing my hands.
“We…We,” I cleared my throat, “We need to talk, Justin. I think after we eat you need to go home.”
Justin put down the remote and looked at me and smiled, “Why are you sitting way over there? Why don’t you come over here and sit on my lap?” He patted his thigh. “We can talk just as well with you sitting on my lap.”
“Stop it, Justin. I am serious. What we did by the pool and what you did to me…”
“You are referring to how I got you off by jerking your nice cock and making you orgasm so quickly and so hard you shot your cum all over the place?” Justin interrupted me. “If I remember correctly you told me not to stop and how good it felt.”
I blushed but nodded my head, “Then what you made me do to you after…”
“You are referring to how you sucked my cock and swallowed all of my cum and even tried to milk it for more?” He interrupted me again. “It was an incredible blow job by the way and I did not force you. You were more than eager to do it so don’t say I forced you. A white man could get into serious trouble in today’s environment if a black girl or any girl for that matter says she was forced to do something she was more than willing to do.” He teased me.
I blushed again, “I am sorry. You are right. I should not have said you made me. Then there are the pictures you took. I need you to delete them, please.”
“You are referring to the photos of you taking off your bikini and posing for me in various, sexual ways? Again, something you were more than willing to do. I saw how hard it made your cock. All you had to do was so no and I would have stopped.”
“I did tell you I did not want to,” I said in my defense.
Justin chuckled and I got the feeling he was mocking me. “No, you never used the word no when I took the photos. You kept telling me how you should not be doing that and how it was wrong and how it was embarrassing when you showed and spread your ass for me, but you never said no or to stop. If memory serves, you took off your bikini rather quickly.”
“I…I was scared you would hurt me if I didn’t,” I lied.
He was right. When he told me to take off my top I did not tell him no or to stop, all I said was “Justin, please.” He was also right that I did take off my bikini rather quickly, much quicker than a good girl like me should have. I could have lied once more to myself and tell myself I did it because I was scared, but the truth was I did it because it pleased the boy, and once again I was falling into my same pattern of pleasing and submitting to my lover’s kinks and fetishes and doing things to them and for them, I knew I should not be doing or that I was not comfortable with.
In the last relationship I was in, I was twenty-three and the man was thirty-four and he liked for me to occasionally fuck his butt. It was not every time we had sex occurrence but there were times he would have me do anal sex to him. I was not much keen on being a top person but I did it because he wanted me to. Yes, it felt good and I would get sexual pleasure from it but I would much rather not do it.
Justin laughed at me, “That is bullshit and you know it. You know I was not going to hurt you and all you had to do was say no. It turned you on and you can’t deny that.” Justin gave me a mischievous smile, “I have pictures of your hard cock remember. You liked it. You liked how slutty it made you feel. You liked doing something so dirty that got you out of your comfort zone and you liked showing your body off to me.”
I opened my mouth to say something, to deny what Justin just told me about myself but no words came out. I sat on the sofa for at least five seconds with my mouth hanging open.
“Answer me this, Tamara,” Justin continued. “What are you going to do? Run tell my parents? Tell them how you allowed their seventeen-year-old son to jerk you off, how you sucked his cock, and how you then posed for some rather risqué photographs for him? I would like to hear that conversation.”
I blushed again, “Well, I would like them deleted, please,” I asked in a whiny voice.
“I don’t think so. I think I am going to keep them. I think you should get used to having your picture taken like that because I intend to take many more of them like that. Maybe even some videos of you posing and jerking off for me, yes I think I would like that. You being my personal, sexy tranny porn model will be fun. I will send them to you so you can have a copy of them,” Justin told me with confidence in his voice.
“Justin, please,” I whined again, “They…they are photos of me and I have a right to ask you to delete them and you should and you are crazy if I am going to pose that way again for you and the hell if I am going to let you make videos of me. I don’t want a copy of them.” I suddenly thought of how I could get him to delete the photos. “Plus, you are only seventeen and if you get caught having photos like that on your phone you could get into trouble legally and…and don’t use the words tranny or shemale. I find it offensive.”
Justin laughed, again making fun of me, “No, Tamara, I can’t get into trouble. True, my parents would be mad but nothing legally wrong with it because you are over eighteen. There is nothing illegal with a seventeen-year-old boy looking at photos like that. My mother would not like it but a teenage boy who likes porn? Hell, that’s considered normal. Now you on the other hand, what would my mother say knowing her friend posed like that for her young son? Tsk, tsk, you should be ashamed of yourself for being such a slut.”
“I am not a slut,” I muttered under my breath.
“Maybe not yet, but we will work on that,” Justin grinned at me. “Now come over here and sit on my lap.”
“No, I told you we need to talk.”
“We can talk while you sit on my lap.”
I looked at Justin and sighed, “No funny business.” I told him.
Justin chuckled, “Funny business? What is this, a nineteen sixty’s romantic comedy with Rock Hudson and Doris Day?”
His arrogance was getting intolerable. “Just promise me you won’t try anything.”
“I promise I won’t make you do anything you don’t want to and if you say stop I will stop. That’s the best I can do. I can’t help but try something since you are so adorable and sexy.”
That was the best I was going to get and I trusted he would stop anything if I told him no. I took a deep breath and stood up and started to walk the short distance to Justin when his voice stopped me.
“But you have to promise something also.”
“What is that?” I asked standing in the center of my living room.
“That if you enjoy what I am doing to you and it makes you feel good then you won’t tell me to stop. You won’t say no.”
I bit my lower lip and nodded, “I promise,” I lied. How hard is it to say no, right?
I walked to Justin and sat on his knees not his lap. I did not want to get so close to him and give him the wrong idea. I flinched when Justin put his arm around my waist; not in fear of him but in fear of how it made me feel. I liked it. He put his other hand on my thigh and like when by the pool he ran his fingers up and down my thigh in a sensual manner. I got goosebumps and shivered. My semi-erect penis became completely erect quickly. I allowed Justin to caress me like that for longer than I should have, but it just felt so nice.
I was surprised I had a full erection; I was surprised I had gotten one out by the pool when Justin was taking photographs of me. Yes, I was so embarrassed when he told me to take off my bikini and the poses he had me in, but it was arousing. I had never done anything like that before and it made me feel naughty and wicked and I liked the feeling. I was surprised I had gotten an erection then and had one now because I had just cum not too long ago. A side effect of hormone replacement therapy was your ability to get an erection, maintain an erection, and could even affect your orgasmic fluid.
When I first started HRT when I was sixteen I could not get an erection for about three or four months no matter how hard I tried. I could orgasm but my cum was a clear thin liquid and sometimes I would orgasm and nothing would come out or very little would. It improved over time but there were still times I had trouble getting an erection or maintain one regardless of how aroused I was and my recovery time from one erection to the next was also affected at times. I could get a full erection and have an orgasm where my cum was thick and abundant as I did when Justin jerked me off by the pool.
The first time I would orgasm when I have not had one in a while, like a day or so, I would cum very quickly. The second time would take me longer, the third even longer, and if I was able to get another erection it would take me even longer, and sometimes I would not orgasm at all. That was very frustrating. Being aroused and having an erection and not being able to cum. The times I could not get an erection but was in a sexual situation I would be aroused, one can be turned on but not get hard, and if my flaccid cock was being played with I could still cum. It would take a long time and my cum would be thin like sticky water, but I would get sexual gratification from it. Sometimes during sex, my ability to get an erection was like a crapshoot, I could never be sure of it. Regardless of whether I could get an erection or not, I still loved sex a great deal and would become very aroused.
At the moment I was sitting on Justin’s lap and his arm around me and his hand stroking my thigh I had a full hard-on. Maybe it was because I had not been touched by a man the way Justin was touching me in such a long time.
“I thought you wanted to talk?” Justin’s voice brought me out of my trance.
“I’m…I’m sorry?” I asked, my mind was fuzzy and unclear. I was not apologizing but was so enjoying Justin’s caress that I did not understand what he meant.
I did not know what he meant by talk. I was so confused. I knew I should not be enjoying his touch and it should not be arousing me the way it did and I knew it was wrong in many different ways, but I could not make myself ask him to stop. It was not so easy to so no apparently. Justin chuckled and his hand on my thigh went higher up and his arm around my waist pulled me even closer against his body and on his lap. His cock was hard also. I could feel it pressing into me. Justin reached up and brushed my hair over my ears and exposed my neck. I made a whimpering sound. His hand then went back to my naked thigh; this time he placed it on the inside of my thigh and much closer to my crotch.
“I am going to kiss your neck now, Tamara,” the boy told me. “You can talk if you want to as I do, but there is no need. I know what you are going to say. You are going to tell me this is wrong, I am too young, what would my parents say if they found out, and other things to try and justify us to stop.” I then felt Justin’s lips on my neck and I moaned. He kissed and even licked my neck and I did not resist in any way. “The thing is, Tamara,” Justin whispered in my ear, “you don’t want me to stop do you?”
The boy started kissing and licking my neck again. It was so sensual and erotic and felt so good. His hand then slid up my crotch and he started rubbing my erection through my shorts. Again I moaned and allowed him to touch me. I even spread my legs for him.
“Uhhh…why…why are you doing this, Justin,” I asked through my panting and heavy breathing.
Justin licked my ear lobe and I gave a soft gasp. I liked my ears kissed and licked. “That should be obvious,” he whispered.
“I…no I…I mean, why me? Why now?”
“Because I want to jerk your cock again until you cum, you suck my dick again, and then I am going to fuck your tranny asshole,” he told me with his arrogant confidence.
I let his comment and him being an asshole pass. “No I mean…oh God that feels nice…I mean…Oh God, Justin, please stop. I can’t concentrate with you doing that.” As I was trying to talk the seventeen-year-old boy kept kissing my neck and his hand kept tracing the outline of my penis in my shorts. He stopped and I continued, “I mean what you expect? To just fuck me today and fulfill this newfound fetish for transsexual girls? It’s not a lack of sex for you I am sure. You have a girlfriend. What about her? Are you going to tell her you fucked some tranny whore? Not that we are going to have sex by the way. I am not a whore, Justin. What if we had an affair, your parents would never speak to me again and I would be lucky they didn’t call the police for having sex with a minor.”
Justin brushed my hair back over my ears again. It had fallen over my face when he stopped kissing my neck. “Well first of all in Georgia the age of consent is sixteen and unlike some other states that include the sixteen-year-old having sex with someone over eighteen. So legally it’s perfectly fine. Now morally is a different story. True if someone found out you are fucking a seventeen-year-old boy since you are twenty-seven they would think of you as a whore.”
I snapped my head around to look at Justin, “I never said I was going to have sex with you so stop assuming. If you need it that bad go see Kathy and let her give you what you need.”
The boy chuckled and put his hand back on my thigh. I hated how he laughed and chuckled at me. I knew he was mocking me and I was amusing him. “Oh I fuck Kathy and the sex is great, but Kathy only lets me fuck her twice at the most when we see each other. She tells me I am too big and it hurts her if we do it more.”
Justin started kissing my neck again and l let out a moan of pleasure. I felt a strange sudden moment of jealousy as I thought of Justin having sex with Kathy. Justin kissed my neck for a few more seconds and made me shiver with pleasure when he ran his tongue up my neck and around my ear lobe.
“But you, Tamara, are going to be different. I am going to wear that shemale pussy of yours out. I am going to fuck that tranny ass with my big cock so many times until I am spent and your asshole is stretched so wide you could put a basketball up there,” Justin said in a matter-of-fact tone.
“I have fantasized about fucking you for a long time,” Justin continued. “I have jerked off so much thinking about the things I would do to you if I made you my tranny whore and this summer I am going to do them. Maybe even longer if it still amuses me. We are going to have a lot of fun together.”
I was taken back by his confidence in what he was telling me he was going to do to me and by the crudeness in the way he said it. I liked dirty talk during sex or foreplay and I have been known to say some rather nasty things myself to a guy under what I felt was the right circumstance. I did not think right then that was the right circumstance. I gave Justin a disapproving look.
“What…and…and I don’t have a say in this,”
Justin grinned at me, “Sure you do. All you have to do is say one simple word. All you have to do is say no.” I made a louder whimper when he yanked on my hair. “It’s not going to be a one-time thing either. Naturally, we can’t date…”
“Why because I am transgender? You will be ashamed to be seen with me?” I said a little too harshly than intended. I don’t know why I even said it at all. It was not like I was going to date him anyway or let him fuck me.
I let out a gasping, high-pitched eeking squeal when Justin pulled my head back by my hair. I like rough sex just as much as I liked intimate lovemaking and found both equally satisfying. During rough sex I liked having my hair pulled, my ass spanked, dirty talk, being called dirty whore, and all that. During those moments I always felt like there was this undiscovered pleasure sensor in my brain that would trigger and increase my sexual arousal tenfold. When Justin pulled my hair that sensor triggered and after I let out my squeal I moaned with pleasure.
“Don’t get all high and mighty, Tamara, or play the transgender hate card on me. You know all too fucking well what I meant. You know I meant we can’t date in public because as you pointed out if my parents found out they would never talk to you again and tell everyone what a whore you are. There is the age difference and while I would have no problem for people to know I am fucking a pretty, sexy twenty-seven-year-old, it would not go over well for you. Also, I am in a relationship with Kathy and she would dump me for fucking your tranny ass.”
During Justin’s proclamation, he kept pulling my hair harder and I was whimpering but God did it turn me on. I flinched with even more pleasure when Justin’s other hand touched my penis again. Unlike before when he was just tracing the outline of it over my shorts, this time Justin formed a loose grip on it and started jerking my cock over my shorts. The combination of him talking to me about how he was going to fuck me, pulling my hair, and rubbing my penis was too much pleasure for me to resist him anymore.
Justin knew what he was doing to me and how he was making me feel. It was very obvious by the way I moved my leg and draped it over his left thigh to spread my legs apart, how I leaned back against his body, and how the fingers of my right hand dug into the leather arm of my chair. Justin knew how aroused I was and how I was not going to resist him anymore by how my breathing increased, how I started grinding my butt against his hard cock in rhythm with his hand rubbing my cock, and the sounds I was making. Besides the moaning sounds coming out of my mouth I made a hissing, sucking noise through my teeth, one of the sounds I made when my cock was being played with or when I masturbated.
Justin let go of my hair, but only for a second; just enough to gather more of my long, blue hair in his hand, twisted it around his fingers, and pulling it hard once again. I gasped out in painful pleasure. He started kissing and licking my neck and ears.
“You like that don’t you, Tamara?” he whispered in my ear. Thinking it was a rhetorical question I did not answer, Justin pulled my hair harder, “Answer me.”
“Y…Yes…I…I like. It feels so good. Please, please baby, don’t stop.”
“I am going to jerk your cock off until you cum again, Tamara,” Justin taunted me in his whispers. “Then you are going to suck my cock again. This time I am going to let you enjoy it more. You are going to lick my balls, my scrotum, and then I am going to shove my big cock down your throat and make you take every inch of it until you choke. Is that want you want, whore?”
“Yes, Justin, Oh my God, yes….just please don’t stop. I will do anything, please make me cum again,” I begged.
Justin pulled my right short’s leg high up my thigh to my crotch, ran his hand up the leg of my shorts and under my panties, and I grunted as he grabbed my cock and pulled it out. He exposed about two inches of my hard cock from under my shorts. The boy brought his hand about an inch from my mouth.
“Spit on my hand,” he ordered me. I did not spit on his hand but instead dribbled some of my salivae on his palm. I felt that was a more lady-like action. “More,” he told me. I gathered a large amount of my spit in my mouth and slobbered it on his hand.
Justin rubbed his hand over my exposed cock head to get it wet with my spit and he then used his fingers to massage the tip of my penis.
“Ohhh, God…uhhhh…that feels so good, baby, please don’t stop,” I moaned.
“You sock is so sexy, Tamara,” Justin went back to whispering in my ear. “I may even suck it later. After all, it’s not a guy’s cock; it’s a girly shemale cock. You would like that wouldn’t you?”
“Ohhh, fuck, Ohhh God, yes….uhhh yes, baby.” He was driving me crazy with pleasure and desire as he rubbed my slippery cock head.
“Spit on it again,” He ordered me once more as my saliva started to dry. I bent over and dribble a large gob of my spit on my dick.
“Then we are going to have some more fun. More pictures of your tranny ass and tranny cock. I may make a video of you jerking off and showing off that tranny ass and tranny pussy,” still rubbing my cock and pulling my hair Justin continued. “Then I am going to fuck you, Tamara. I am going to wear that tight asshole out. You are going to become my bitch, Tamara. I am going to play with you and fuck you anytime I want. I need something to amuse myself with during this Covid shit. That’s what you want isn’t it?”
“Yes, Daddy, yes I want that. I want you so bad, Daddy. I will do anything Daddy wants me to. Please don’t stop.”
Justin let go of my hair, pulled his head back, and took his hand off my cock. “Daddy? Where the fuck did that come from?” He laughed at me.
“Please, baby, I am sorry, please keep going. I won’t say it again. Please, Justin, don’t stop,” I pleaded.
Justin’s hand went back to my exposed cock, I dribbled more spit on it, and he continued massaging it slowly, teasing it with his fingertips. “Is that what you want? A daddy to take care of you? A daddy to tell you what to do? A daddy for you to pleasure with your mouth? A daddy to fuck that tight shemale pussy?”
“Yes, Daddy…ohhh, please make me cum…please, Daddy. I will be a good girl for you. Please don’t stop.”
I let out a cry of pain when Justin grabbed my cock head and squeezed it hard. “I am not your fucking daddy, you whore. I am not going to satisfy your daddy issues.” He squeezed my cock harder and I cried out. “Understand?”
Just at the moment, my doorbell rang and I was saved the embarrassment of why I called him “Daddy”, but I still wanted him to go back to rubbing my cock. Instead, Justin pushed me off of him and I fell on the floor as he stood up. I looked up at him and then my eyes fell on his large bulge in his crotch and I swear my mouth started to water.
“Lunch is here,” the boy said calmly.
I reached up and started rubbing his penis. “No, please, baby. They can leave it at the door. Please.” I begged like a shameless hussy. Earlier was very hungry but now food was the last thing on my mind.
Justin pushed my hand away and smiled at me. It was not a kind smile at all or even an amused smile. It was a smile that told me he had me now and I would be his. “No, we can’t leave it at the door. One or more of Mrs. Habersham’s cats may smell it and eat some of it.”
Mrs. Habersham had four cats she let outside that roamed our neighborhood. I hated them. Not because I hated animals, but because I was deathly afraid of cats. One time two of them decided to hang around on my front porch and would not leave. I ended up filling a cooking pot with water, opened my door, and quickly threw the water on them. Don’t judge me! At least it was not hot boiling water, which the thought did cross my mind.
The doorbell rang again. “I need to piss so go get our food,” Justin commanded me and walked to the bathroom.
I got off the floor, tucked my erect penis back into my underwear and shorts and looked down, and was satisfied that my hard-on could not be seen. I went and answered the door to get our food. The Uber Eats delivery person was a man I knew from him delivering food to my house in the past and he knew me by name and I knew his. We had chatted in the past when he would deliver food and I had gotten to know a little about him. Tony was a nice man in his late thirties, married, and had two kids. He was laid off from his job at a local insurance office due to the office closing down because of Covid and got a job for Uber Eats. I felt sorry for him. His wife was a nurse so at least they were not struggling too much but hoped he could go back to work soon.
I need to take a brief moment to explain my calling Justin “Daddy”. I didn’t have daddy issues per se. My father was very supportive of me being transgender and he or no one ever “bad touched me”. He did not have a biological need to pass on his genes to a son. I have an older brother who is two years older than me, masculine and athletic. My brother went to North Carolina State University on a basketball scholarship and while not good enough to make it into the NBA he did have the talent to play European Ball and was currently in Europe playing for a professional basketball team in Italy. My father did not need a masculine son, he already had one.
When I came out to my parents as transgender I did all the right steps with their support. I think they kind of suspected or knew anyway based on how feminine I was. I went to a gender therapist for a while and then got a letter of support to give to a physician who specialized in Hormone Treatment Therapy and continued to see the gender therapist for a few years. Once I came out my father started to treat me like a daughter, which was great, and soon I became daddy’s little girl. He spoiled me as such and we became very close like a father and daughter, but not in a perverted manner. Yes, maybe he did go overboard at times to make me feel more comfortable during the difficult period I went through when I started my transition. I did start to crave his approval and tried to be the perfect daughter for him. Maybe I did have a small daddy issue.
Then there were the men I had been with on a sexual and intimate level. In the last relationship I was in the man was much older and he liked when I called him daddy during sex and I did often. The one-night stand I had with a man he also liked when I called him daddy as he was fucking me. In the erotic books I read the transgender females often called their lovers daddy. In college one of my transgender roommates would refer to her lovers as daddy. I got the impression that is what men wanted to hear from their lovers so I started using the term and I had to admit I liked it and it turned me on. I promised Justin I would not call him daddy, but I could not guarantee it would not slip out during sex or in an intimate moment with him.
I took the food into the kitchen, laid it on the counter, and got a plate for Justin’s sandwich and a bowl for my salad my cabinet and flatware from a drawer and set the dinette table in my kitchen. I hated eating out of the container food was delivered in. I put some salad in my bowl and closed the lid to the container and put it back in the refrigerator. It was a big salad and I would not be able to eat it all.
My head was spinning with confusion. That I was going to have sex with Justin was no obvious no matter how wrong I knew it was. Things had progressed to the point where I could no longer deny my attraction to him and my desire for him. I was sexually attracted to the boy’s arrogance, his confidence, and his dominance over me.
What confused me and made my head spin, was if I was going to go through with everything he told me he was going to do to me. Was I going to allow him to take more photos, allow him to even video me, allow him to use me as a fuck toy all summer as he said he was? How was I going to face his mother and father after I had sex with him? They would hopefully never find out, but I know I could never face them with a clear conscience even if they never knew. Maybe I should just have sex with him this one time and that will be the end of it.
“You have a great ass, Tamara.” Justin’s voice gave me a start. “So sexy.”
I turned and smiled at Justin, “Thank you.” I was holding two forks as Justin walked to me. “What…What would you like to drink?” I asked. The look of desire in his eyes made me nervous. I turned back to the table to finish setting it.
I was not nervous because Justin doing something to me that would be inappropriate. We were way past that now. I was nervous about the idea of having sex with the teenage boy. I had not had sex in so long and I was hoping I would not embarrass myself and the size of his penis did intimidate me. I knew since the only thing I had up my ass in the past four years was my small, thin six-inch fake penis and his length and girth were going to hurt. There was one more thing I was nervous about when Justin did eventually fuck me that afternoon.
This will be the only time I mention this in my story because it is embarrassing and vulgar and I don’t like to talk about it, but since this is a true story I feel it needs to be mentioned. There is a slim chance that anal sex can get messy; it’s a low probability but it can happen. I practice impeccable personal hygiene including my asshole. Let’s face it when my mother gave me the sex talk she tried to be prepared and did her best but she knew very little about how to give a sex talk to a transgender female. It was a highly embarrassing conversation for both of us and mostly the “talk” was her handing me pamphlets on male same-sex relations. Before I lost my virginity I did a lot of research on anal sex and how to prepare for it and what to expect. When I am in a sexual relationship I do use an enema about once a month to better clean myself in that area for sex. Using an enema more often can be harmful and it’s not needed much more than that as long as you practice good hygiene daily.
I had not had sex in almost four years and I was not expecting it that day at all so I had not used an enema in a very long time. Chances were I would be ok since I did clean myself in that area when I showered, but Justin was very large I was worried something may go wrong. A condom would have been the best thing for us, but I didn’t have any in the house and I know Justin didn’t have any because he just brought the clothes on his back and his cell phone. I preferred to be barebacked anyway if I knew the guy was free of any STDs, which I was positive, Justin was. I liked the feeling of a man cumming in my ass. I didn’t know if Justin knew any of this but I suspected he did. If he had read the websites, the forum posts, and chatted with people who dated or were transgender then that subject would have come up.
My concerns vanished from my head when Justin came up behind me when I was setting the table. He wrapped his arms around my waist, moved my hair from my neck, and started kissing the back of my neck. I moaned and reached around behind me and started rubbing his erect penis. His shorts were dry now.
“Justin, I’m hungry,” I giggled as his lips tickled the back of my next.
“I have a confession,” he told me as he ignored my comment. “I did not come over here to come swimming.”
Justin chuckled and turned my body around to face him. I wrapped my arms around his neck and pressed my head into his chest. Justin ran his hands up my legs and in one quick jerk he pulled down both my shorts and panties and then put his arms around my waist again. He then leaned down and I raised myself on my toes and we kissed.
I realized it was the first time we kissed each other that afternoon. I loved kissing and I wasted no time in parting my lips and allowing his tongue to enter my mouth while I used my tongue to twirl and dance around his. It was a very passionate kiss and Justin was a good kisser. As we kissed my hands ran up and down his back and his hands fell to my ass and he cupped it. I gave a giggling squeal as Justin lifted me and sat me on the dinette table.
“Justin, stop. I eat on this table,” I told him but kept giggling and kicked off my shorts and panties that had fell to my ankles.
My giggling turned into soft whimpers when Justin took my penis in his hand and started slowly running it up and down my shaft. I reached down and tugged his shorts several times until I was able to pull them down and his huge penis sprang up.
“Justin, let me suck it again. Please, baby, I want to feel it in my mouth again,” I pleaded.
“Shhh,” The boy told me. “I let me talk and then we can play.” I nodded and let Justin continue as he still ran his hands up and down my cock. “I have wanted you for a long time, Tamara, and I finally got up the courage to try and fuck you. I didn’t expect you to let me but I had enough of thinking about trying so I just had to at least try.” He kissed me again and I responded.
Justin broke the kiss, “I came over and knocked on your door but you did not answer so I came around back and saw you by the pool. I saw you touching your cock and how hard it was.” I blushed but did not say anything. “I knew I had to take my chance so I quickly developed a plan. I took off my underwear, knowing when I went for a swim you would be able to see my cock under my wet shorts. I know I have a large dick and I was hoping you would notice.”
“I did,” I made my confession.
Justin grinned, “I know you did and I thought if you were horny enough to be rubbing your cock by the pool maybe you would get turned on by seeing my big, hard cock.”
“It…ohhh God that feels so good,” Justin started rubbing my cock faster, “It is so big, baby, and it did turn me on,” I said that a lot to the few guys I have had sex with; they liked hearing it, even when they had an average-sized penis. With Justin, I was not lying. He was very well endowed.
“I was shocked you let me take those pictures,” Justin smiled at me.
“I…I should have not let you…oh fuck, baby don’t stop.”
“It turned you on, didn’t it? Posing for me like that? Admit it?”
“Yes…it, it did. I thought it was humiliating but it turned me on,” I admitted. I don’t think I would have admitted that if he was not touching me like he was.
“Take off your shirt and bra and lean back on the table.”
I took off both and moved some dishes out of my way and leaned back on the table as he told me. Screw it. I can always disinfect the table, I thought. If he wants to fuck me here then let him. My dinette table was well built and very sturdy. I propped myself up on my elbows so I could see his hand on my cock, I liked to watch. I had a little bit of voyeurism in me and based on how aroused I got from Justin taking my picture as he did, I also had a bit of exhibitionist in me as well.
My chairs to my dinette table had cushions on the seats that tied to the chair to hold them in place. I watched as Justin untied a cushion and placed it on the floor. I had no idea what he was doing. He then knelt on the cushion, I sat up, Justin took my cock in his right hand, and he looked up at me.
“I never did this before and I don’t mind doing it to you for a little bit. To me your cock is not a man’s cock but a girl’s cock, but don’t ever cum in my mouth. You cum in my mouth and I will be very pissed,” Justin told me.
I nodded my head. I knew what he was going to do and I wanted him too badly. “I promise.” I then let out a loud whimper as Justin squeezed my erect cock tight.
“I am serious about you not cumming in my mouth.” The tone in his voice was more authoritative.
“I…I said I promised,” I whined out.
He was hurting me but once again his dominance over me aroused me. I had a weakness for dominant, authoritative, and confident men. Weeks later I found out what he meant by “very pissed” when I accidentally did cum in his mouth. It was an accident and I came so fast and it was one of those surprise orgasms and I could not stop it. After he gagged, coughed, and slobbered out my cum, Justin took his leather belt and whipped my bare ass and the back of my thighs with it until I was sobbing and begging for him to stop. I had never been spanked like that before as punishment. Not even by my parents when I misbehaved. My dad used to use his belt on my brother until he outgrew it, not in an abusive way but as punishment when he did something really bad; but he never struck me in any way. It hurt terribly but Justin’s discipline of me like that did turn me on. Not to say I wanted that again. I may be the submissive person in a relationship but I am no masochist. He left welts and I never came in his mouth again. The odd thing was I felt he was right in punishing me. That I deserved it.
Justin loosened his grip and lowered his head and took my penis in his mouth. It was not the best blow job I had ever gotten, it was his first time, but damn it felt good. It was a blow job after all. He didn’t take me far into his mouth, only about three inches, but he did use his tongue on the head of my cock to make circular motions around the tip.
“Uhhh fuck, baby, that feels good,” I moaned. “Oh, baby, your mouth feels so good on my cock…uhhh fuck, Justin…that’s it…ohhh God, yes… jerk my cock, baby.” I moaned louder when Justin took my cock in his hand and stroked the shaft while he sucked me.
I was enjoying watching him give me a blow job and I put my hand on Justin’s head. He moved it away and took his mouth off my penis. “Don’t. Don’t ever do that,” he told me.
Justin sucked my cock for about two minutes and then he took his mouth off my penis and just started jerking me off. My penis was slick with his saliva and his hand glided up and down my shaft and head of my cock. I sat up on the table to watch him, making whimpering and hissing sounds through my teeth once again.
“Spit on it,” he told me when the saliva started to dry.
I leaned over my cock and dribbled spit onto the tip as Justin continued to masturbate me. I did that three or four times to get my cock slick for him. As he jerked my cock the boy kept asking me how good it felt and didn’t I like it; he also taunted me and kept telling me I was his tranny whore or his tranny bitch.
“Uhhh…Uhhh…baby, I’m cumming…uhhh fuck…uhhh…I’m cumming,” I moaned as I felt my orgasm impending.
Justin started to jerk me harder and faster. I was looking into his eyes that were focused on my cock. I saw a sudden sparkle in his eyes as he grinned mischievously. Justin started jerking me slower as he stood up, reached behind me, and grabbed my salad bowl. He started masturbating me hard again and held the bowl filled with my lunch in front of my cock.
“Uhhh…please don’t…uhhh…uhhh please…Just…uhhhh God…cumming….” I tried to tell him no and tried not to cum but I was past the point where I could stop myself or even move away from Justin.
Justin pointed my cock at the bowl as my cum shot out of my penis. I moaned and grunted as I came and my body spasm from my orgasm and Justin kept jerking me off. My cum was thinner than it was the first time but there was still a lot of it and it splashed all over my salad. When I could cum no more Justin stopped, lifted his hand to my face, and wiped his hand on my left cheek and then through my hair as I sat on the table panting.
I watched as the boy took a piece of sliced cucumber from the salad and he brought it to my lips. I closed my mouth tight and shook my head. The cucumber slice was glistening with my sex fluid.
“Open up, Tamara, you said you were hungry,” Justin chuckled as he ran the cucumber over my lips.
I opened my mouth and the teenage boy fed me the cucumber. I chewed and swallowed and then licked my lips to taste the cum that Justin spread on them. Justin laughed at my humiliation.
“God, you are a nasty slut. Want more?” He teased me.
I blushed and felt humiliated but I also opened my mouth and nodded. This time Justin fed me a cherry tomato, also glistening with my cum. I chewed and swallowed it and opened my mouth for more.
“No, we are done with lunch for right now. Your salad needs more dressing,” he told me.
Justin grabbed a handful of my hair and pulled me off the table. I squealed and whimpered and once off the table, he pushed my head down. I knew he wanted me on my knees and I knelt on the cushion he was using.
“Before you finish your lunch and we play some more I need to get off. I am very horny and need to cum to make our fun last longer.” Justin’s long, thick cock was jutting out in front of him almost touching my face. “Suck my cock but this time you can take your time and enjoy it.”
I took his cock in both of my hands and moved my head to his crotch.