Date: Fri, 3 Nov 2023 13:29:49 -0700 From: Pomo Wolf Subject: Momma's Trans Boy (Gay/Trans, Adult Youth, oral anal, F/m FFFM) Trans, Adult Youth, oral anal, F/m FFFM This story is a work of fiction and contains descriptions of explicit sexual acts between consenting woman and male youth. If this type of content offends you or you are under the age of 18 do not read it. If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available. You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored. Momma's Trans Boy By Wolf I'm a liberal middle-aged woman that had my only child when I was thirty-one-years-old. I deliberately sought out a fellow worker at the phone company I worked with and asked him to impregnate me. It took some persuasion on my part to talk him into helping me out. He happened to be a handsome openly gay guy, and I am an openly kinky lesbian. I had to put it in writing that he had no financial obligation to any issue I conceive. I wanted him to fuck me until I got pregnant. (Artificial insinuation just didn't appeal to me.) Not that I looked forward to having a male penetrate me and sweat over me. We agreed that he would come to my apartment during the first couple of days during my fertile period and fuck me three days straight. In hopes that I would conceive a female child. It only took a couple of months before I tested positive, but nature didn't concur with my plans. It didn't take long before my obstetrician informed me that I was going to deliver a male infant. I reconciled myself to go through with the pregnancy. My gestation was normal and delivered only four days earlier than projected. When the nurse placed the baby on my breasts, I was very emotional when I saw the tiny little boy. The umbilical cord was still attached. The doctor cut the cord and she asked me if I wanted to have him circumcised, but I cringed at the idea of having skin cut off his little body. During the pregnancy I had bought everything needed for a nursery and made plans for a nanny to look after him while I was at work. The phone company already had a room set aside for nursing mothers and a fridge to store milk bottles. I even had a milking machine to be able to milk my tits when necessary. I'm sure my fellow employees made a lot of rude comments behind my back because all of them knew that I'm a dyke lesbian. I am five-feet five inches tall, with a slender body with narrow hips and small breasts. (At least having a baby did increase the size of my breasts a little.) My hair is cropped short and was turning gray at thirty. I have a long and narrow face. When I smile, a lot of teeth show, and my blue eyes are large. When I wasn't working, I devoted most of my time to the boy I had given him the name Gerry Lee Grimes on his birth certificate. Becoming a mother didn't stop me from entertaining women. I knew several women that I could invite over and spend the night with me. As Gerry grew up, he was accustomed to having women around all the time. I don't truly know when he became aware that I kissed them and touched them a lot. He must have been about six-years-old when he woke up because he either was frightened by something or felt sick. When he crept into my bedroom, he witnessed a naked young woman with her face buried in my crotch and clinging to my small tits with both hands. He became very emotional because he thought the woman was hurting me, after all I was moaning a lot. I had to disengage myself from the young lady. I wasn't concerned about him seeing me naked. I wasn't modest and didn't want him to be curious about the physical difference between us. As I carried him back to his bed, he asked me why that woman was hurting me. I simply told him that she was making me feel good. I stroked his belly until he went back to sleep. When I returned to my bed, the young lady was a little put out, because I had left the bed before I had satisfied her itch and her body was cooling off. It didn't take long to warm her up again. She sang my praises by the time I finished. I must admit that Gerry walked in on me entertaining young women many times. He began identifying with women. He witnessed me fucking a woman in the ass with a strap-on dildo one time, and asked why I didn't make love to him like that? I began to wonder if he would be eligible for sex reassignment. I caught him putting on my underpants, nylons, and bra many times. I even taught him how-to put-on makeup. He made a cute looking girl. I discussed the idea with my gynecologist. She interviewed Gerry along with psychologist. They agreed that he was a perfect candidate for sex reassignment. He was put on a hormone treatment to increase the female hormones and prevent him from the increase of male hormones during puberty. As a result, he began to look more and more like an adorable girl. My lady friends were amused by watching my son trying to act and dress like a girl. They even supplied him with items of clothing. By the time he would have entered puberty and discovered the pleasure of masturbation. He was identifying as a girl, but he enjoyed playing with his penis just the same. I didn't reprimand him for playing with himself. I let his red hair grow long enough to style like a girl, but insisted that he wear it in a ponytail at school, because it was going to be a traumatic experience when we were going to have his sex changed to female legally. In the meantime, I had to remind myself that I had to address Gerry with female pronouns. She enjoyed getting dressed up like an erotic parochial school girl. She would put on a white blouse with a black velvet bodice that pushed up her tits, a pleated plaid mini skirt, a garter belt to hold up her nylons, and Mary Jane black pumps. She just didn't put on panties so that when she got a hard-on it tented out the spirit. One day I saw her admiring herself in my full- length mirror with her penis and scrotum tucked back between her legs. She looked so much like a cute young girl that I had to hug and kiss her. Gerry pleaded with me to fuck her with my strap-on dildo like I did to some of my girlfriends. I assured her that it was going to hurt, and she would have to endure the pain many times before she would learn to enjoy the feeling of a cock in her ass. She insisted, so I obliged her. I pulled out my nightstand drawer and took out my strap-on dildo and a bottle of lubricant. She watched me step into the harness and tighten it up. Then I dribbled the lube all over the shaft of the rubber phallic device and my greasy fingers to grease up Gerry's asshole. Just as I had predicted she whined like a baby as I predicted as the dildo spread her sphincter. I fucked her until Gerry was exhausted. I knew enough about male anatomy to know that the thin colon lining rested against the prostate. Gerry suddenly ejaculated without touching her penis. She was thrilled to learn that she could cum while being fucked. It was worth the pain to her. I felt even closer to her than ever before. I no longer needed to invite women to spend the night with me. I had a daughter spend her nights in my bed. One Saturday after fucking her half of the night. I got up late and went to the bathroom to relieve myself, bathe, put on my face, and brush my hair. Then I went to the kitchen to prepare a brunch for the two of us. I tossed English muffins and poached eggs and made my holiday sauce with a little horseradish to give it a little bite. I put out a couple of small bowls filled with diced mixed fruit, and brewed coffee for myself and poured milk for Gerry. When Gerry didn't make an appearance, I went looking for her. I found her lying on the bed with her mini pleated skirt and garter belt attached to her nylons. She was on her side with her sex organ tucked between her thighs and was reaching back toying with her asshole. The sight of her playing with herself excited me. I retrieved the bottle of lube and dribbled plenty of the stuff all over her butt, asshole, scrotum, and penis. The skin of her scrotum was stretched tightly into a round-ball being pulled back between her thighs, and her penis had grown into a plump five-inch-long cock with the foreskin completely covering the head. I used my hands to rub her butt and probe her asshole with one hand and masturbated her cock. (We were calling her cock a clitoris now.) I jacked her off before I bent down and sucked her clit until she fed me her cum. When we went to the kitchen the milk had warmed and the holiday sauce had jelled. So, I had to make a fresh patch and pour a fresh glass of milk. One of my frequent visitors knocked on my door shortly after noon. So, I let Gerry fuck her in the ass while I ate her pussy. Gerry became very popular among my girlfriends. When Gerry turned fourteen, we had a birthday party for her and she got to meet her father. Gerry allowed her father to fuck her asshole that evening. If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available.