It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace panties on the living room couch.
My little six inch clitty dick was rock hard and leaking juices into the fine lace material when Ron walked into the living room. He had a perfect view of my fingers playing with my little clitty dick like a girl plays with herself through her panties. Ron smiled widely when he saw my hard six incher.
"Courtney, aren't those your mother's panties, stockings and bra?"
I jumped up at the sound of his voice interrupting my auto-erotic session.
"Oh, Ron. It's you," I said surprised he was there.
"Yes, it is me," said Ron smiling. "But it doesn't look like you. What are you doing wearing your mom's sexy lingerie?"
"Well, she's gone for the whole weekend," I said figuring he should know.
"Really," he said. "Where'd she go?"
"She went to Las Vegas with her new boyfriend," I replied.
"Really?" he said looking sad, suddenly. "I didn't know."
"She just started seeing him," I said.
Suddenly, I was happy to be telling Ron that my mother wasn't coming home, all weekend. As a seventeen-year-old tranny-in-training, I had a crush on Ron still and I often fantasized about having sex with him dressed as my mother. Now, here I was dressed as her and Ron was catching me and smiling about it. Now, I was glad he was hurt that my mom was gone with another man. I, suddenly, saw it as an opportunity to fulfil my fantasy I had about being with Ron.
"Why don't you sit down and I'll mix you your cocktail," I said to him to see if he would stay.
Like a dutiful boy, Ron sat down on the couch and I shook my ass cheeks good for him as I walked to the kitchen to shake up his favorite cocktail. I knew from other men telling me so that my ass looks just like a girl's ass, especially in a sexy pair of panties. I was hoping Ron would already be turned on for me when I got back to the living room with his drink. I knew he had a big cock from the way he made mom moan so loud in bed and I wanted him to make me moan, too.
"So, who's your mom's new guy?" said Ron as I handed him his cocktail.
I sat down next to him and I saw he had a huge bulge in his pants, already. Ron liked to come by on Friday nights and fuck my mom, all weekend long, until Sunday. I was hoping he would stay and do the same for me; after all, I was wearing my mother's sexiest black panties and bra and black stockings with lace trim on the tops.
"She just started seeing him, Ron. He's a professional gambler. But he's not nearly as handsome a man as you are, so I don't think she'll keep him."
I felt like a sexy little vixen wearing my mother's lingerie for her old boyfriend and sitting next to him on the couch telling him how handsome he was.
"So, are you thinking about filling in for her, in the meantime?" he said very to the point.
Ron reached down and rubbed the big bulge in his pants.
"I saw you shaking your little ass for me when you went to make my drink for me, Courtney. And you looked damned good, too. That hot little ass of yours looks as fuckable as your mother's ass."
"I'm sorry she left you for another man, Ron. You were always so sweet, giving her hundreds of dollars a night to sleep with you. I'm sorry she's not here to sleep with you, tonight."
"So am I," he said. "Especially when you're here looking all sexy in her lacy underwear turning me on like she does."
"Really, Ron," I replied. "I turn you on like she does?"
"Of course, you do. And you know you do, Courtney. That's why you wear those sexy little clothes of your mother's. You want to please a man's cock, the same as she does. And from the looks of your hot little ass, I'm sure you can do it."
I blushed at my mother's handsome boyfriend who I knew had a hard on for me, now.
"You want some cock to fill that ass of yours tonight and you know you do, Courtney. Don't say you don't."
Ron reached for the inside of my thigh and started rubbing the silky material of my stocking. The feel of his strong hand on my soft, freshly-shaved thigh made my clitty dick leak juicy pre-cum.
"It looks like your panties are getting wet, Courtney. You must really be hungry for a hard cock wearing that sexy outfit your mother likes wearing, so much. Do you think you'd like to suck a cock, tonight, like your mother does? Do you think you'd like to be fucked in that hot little ass of yours?"
Ron already knew I wanted his cock from seeing me shake my ass when I went to the kitchen. That was a girl's trick I had learned when I was sixteen-years-old. Using her ass to attract big hard cocks to her is one of a girl's most formidable weapons. I had perfected my sexy walk like my mother's practicing in front of a full length mirror while dressed in her sexy clothes. Now, I had used the same walk she did to make her former boyfriend hot and horny for me.
"Like mother, like daughter," I said to Ron.
"Oh, you sexy little thing. I know you're going to suck and fuck me good, tonight. Aren't you?"
Ron leaned toward me to kiss me as I nodded my head "yes" like a horny little submissive bottom boy to his big hard stud. Although he was thirty-five-years-old, Ron was a young-looking, tall, dark and handsome hunk with Hollywood actor good looks I liked as much as my mom did. And pretending to be her and sucking and fucking her good-looking, rich boyfriend all weekend like she did sounded great to me. Since she was out of town, I could wear all of her sexy lingerie, all weekend, too.
Our lips touched and I felt like a school girl in love. I knew his cock was hard for me and I wanted it, badly. While he pressed his lips to mine, I reached down and fondled his big cock in his pants while he rubbed my inner thigh moving his big hand toward my little clitty dick... We were so hot and horny for each other, we were ready to rip each other's clothes off by the time we finished kissing.
"You're a babe just like your mother, Courtney. You have a nice ass and a sweet set of lips. I bet you like putting your lips around a man just like your mother does, having his big cock cum in your mouth and swallowing it for him like she does."
Like a shy girl who is new to sex, I said, "I can try."
"Great," said Ron smiling. "Why don't you take off my pants for me and hang them on the dining room chair? And use that sexy strut you learned from your mother to keep me hard for you while you do it."
I reached down and felt Ron's big cock through his pants like a girl petting her first cock and I knew, right away, that he was as turned on for me as I was for him. It was a strong mutual attraction we had. I reached for his belt with my other hand and removed it while rubbing his cock and he rubbed my soft thigh. Then I reached up and unbuttoned his pants and pulled down his zipper. After opening his pants and pulling down his black cotton briefs, I beheld the same beautiful nine inch cock that had satisfied my mother, so many nights and days.
Without a word, I sank into position to give my mom's old boyfriend his first good blow job of the long weekend. His hairy cock was a full nine inches long with a big mushroom head and a large set of manly balls. His balls were hairy, too, not like my little shaved ones. There was no doubt, he was the stud and I was the pussy boy, not just from the clothes I was wearing but from the size of our sex tools. I wanted to suck his cock really good like mom did and make him want to give me hundreds of dollars a night to sleep with me, too. A girl likes to know a man appreciates her, you know?
I licked the big head of his cock all the way around like a hungry little slut while I looked up in his brown eyes so full of wonder. I felt like a sweet teenage girl having sex with her mother's handsome boyfriend, sucking his cock like she did. I put the big head of his manhood in my mouth and I was, suddenly, okay with it if my mother knew I had sex with her boyfriend. A cock this nice was worth being shamed and humiliated for, although I knew Ron would not want my mother to know, either. And I wouldn't tell.
I had been sucking men's cocks since I was sixteen and I was only seventeen, but I felt like I had a lot of experience with men already. Most of the men I sucked and fucked wanted me, time and again, after the first time. So, I was confident I was good enough at sex to fully please Ron, all night, and the way he liked to be pleased by my mother. Since she was in Vegas taking care of her other rich boyfriend's cock, Ron's cock was going to be mine to enjoy, all weekend.
"Oh, yeah, that's it, Courtney," he said. "Suck it good, just like your mother does, babe. Play with my balls, too, like she does."
I was only putting five inches of his big niner in my mouth each time I bobbed my head and slurped on it, but I was stroking the bottom of it with my little soft girly hand and playing with his big balls with my other hand. Touching Ron's massive meat was turning me on so much. My clitty dick was leaking sticky pre-cum into my mom's panties. I was so glad we wore the same size panties, even though her bras were a little big on me.
I love a man to encourage me while I'm sucking his cock good for him. It made me feel dirty like the professional dicksucker I wanted to become. I loved feeling like a pro when giving men oral because I knew they really liked to be sucked by dirty, horny girls and I loved being a dirty, horny girl for a man's big one. It made me feel so seductive and friendly.
'Yeah, that's it, you sweet little girl. Your mom would be proud of you pleasing men like she does," said Ron. "And I bet you like a big, hard cock inside you like she does, too."
I was busy lapping up his juicy pre-cum with my eager tongue, but I nodded "yes" at his suggestion of fucking my ass.
Women know how to dress to make men want to fuck them. And I was glad to learn how to dress to please men so well from my sexy and glamorous mother. Having her boyfriend telling me that he wanted to put his big cock inside me like he did her told me that I really did look sexy like her wearing her black lacy panties, stockings and bra for a man. And I couldn't have been more thrilled.
"I bet you like to deep throat a man like your mother does," said Ron. "She can put my whole cock in her mouth and suck it when I hold her head down. Would you like me to hold your sweet little head down and let you deep throat me, too?"
I stopped sucking on his niner for a moment.
"I would love it," I said giving him a sexy smile.
Then I put my mouth around the big head of his cock and opened wide. Suddenly, I felt the pressure of Ron's big strong hand on the back of my head and I felt like a submissive little slut ready to have her mouth abused by a big cock. It was already a thrill to me to deep throat a man's big cock for him and I wanted to become a specialist. But to deep throat the same cock my mother like deep throating was even more special than I imagined it would be on nights I laid in bed fingering myself and sucking on my mom's ten inch dildo wishing it was Ron's big cock. Now, I was finally getting Ron's big cock in my mouth instead of the plastic dildo I pretended with. And it was wonderful.
"Oh, yeah, Courtney," he said. "You're a hungry little cocksucker these days. I'm sure that lots of men would like to let you suck them. You know, my friend owns an escort service and he told me he's always getting calls for tranny escorts. But he can't find one. If I refer you to him, I'm sure he would hire you."
I was putting six inches of his hard cock in my mouth and I was still hungry for the rest. And the thought of becoming a tranny escort through my mom's boyfriend sounded exciting to me. But I wanted him to fill my mouth with his hot cum, so I didn't stop to talk. I took my hand from his balls and placed it on top of Ron's hand on my head to let him know I was ready to deep throat him like mom did.
He pushed me down further on his cock with his big strong arm muscle and I enjoyed feeling like the weaker sex. Any big hunk with a big cock was welcome to push me down on his cock and I was so glad that Ron was finally doing it for me. Sexy fantasies do come true and I was glad for the timing of this one. It was just lucky for me that my mom left for Vegas with her new boyfriend without telling her old boyfriend she was going. Now, I was getting to deep throat his cock tonight instead of her. Pleasing a man good with my mouth was such a great turn on for me, I never wanted to miss an opportunity to do it.
I, now, had a full eight inches of his cock in my mouth and I wanted the last inch, too. He was helping me by holding my head down for me and I loved it as I lapped up his cock with my hot, wet tongue. He was definitely getting a sloppy blow job like he liked my mother to give him. It was all working out, wonderfully, for all of us; mom had her new boyfriend to sleep with in Vegas and I had her old boyfriend to sleep with at home to help him get over losing her. If he could get his cock deep throated by me, he wasn't going to miss her very much, this weekend.
Finally, he pushed me down hard on his cock and I was getting the full nine inches in my mouth like a good little whore boy. After all, that was what Ron was telling me to become. Now, he could tell his friend with the escort service about how I swallowed his whole cock good for him. I would be glad to swallow his friend's cock to show him in person, too. Having a man filling my mouth with his cock makes me feel so much like a girl, I don't want it to end. And being an escort would guarantee I was getting lots of big cocks, all the time.
"Oh, yeah, baby doll. Suck it good. Lick that cock, honey," he said to encourage me.
I loved being encouraged to suck cock so much that I was ready to cum down in my little black lace panties, at the same time as Ron came in my mouth.
"Oh, yeah, I'm going to blow a big load in your mouth, baby. And I want you to swallow it all like your hot mother does. In case you don't know it, you suck cock just as good as she does. And I pay her hundreds of dollars a night to let me sleep with her. I'm going to pay you, too, Courtney. And I'm sure lots of other men would pay you to sleep with them, too."
It was all very flattering being told I sucked cock as good as my beautiful mother did and I couldn't wait for Ron to fill my mouth with his hot cum like he did hers.
"Yeah, suck it, baby doll," he said. "I'm ready to fill your sweet little mouth good, right now, you little fuck doll. I see the way you shave your peach fuzz off your legs like your mother does. And you have a hot little ass like hers, too. All we have to do is put one of her blonde wigs on you and you'll be the cutest little tranny escort in three counties. Oh, yeah, suck that big cock, baby doll."
In an instant, Ron's hot creamy cum shot out of his cock and down my throat. I licked at it eagerly with my tongue, trying not to let any drip out, but his load was so big and so sticky it started leaking down my chin and unto his big hairy balls. After I licked it all up off his cock, I licked it off his balls, too. It was sweet and salty, at the same time. And I liked tasting the same cum my mother tasted, for so long.
Ron was a rich married businessman who only came to sleep with my mother on weekends. He would tell his wife he was on a business trip and come and have sex with my mother all night Friday night, all day and night Saturday night and all day Sunday, before leaving Sunday night. Mom would wear her sexy negligees or her sexy underwear under her little silky robes. Every weekend, Ron came to see her, mom never bothered to get dressed. She wanted his cock big and hard for her, all day and night. And I was glad to be taking over for her, this weekend.
"Oh, yeah, suck all of that cum down, baby doll," said Ron. "You know how to please a man, real good, honey."
It was my first blow job of my mom's old boyfriend and I felt like she did when I was done. I had a handsome man with a big cock to please, all weekend. And I knew he would leave me hundreds of dollars on the dresser when he left, so I felt like a paid whore with her john. It was a thrill, in itself, for a man to pay a girl to have sex with him. No wonder mom liked doing it for lots of men who left her money on the dresser; she loved the thrill of it. And so did I, now that I had sucked her boyfriend's cock good for him like she did.
"Oh, baby doll, I know your mother would be proud of you the way you can deep throat a cock, the way she can."
"She should be," I said. "I used her big ten inch dildo to practice sucking."
"Really?" he said smiling. "So, you've wanted men's cocks in your mouth for a while?"
"I've wanted yours in my mouth since I was sixteen. And, now, I finally have it," I said smiling. "It's delicious."
I licked the big head of his cock with my tongue while I squeezed out the last of his hot cum. It was now time to move to the bedroom for some good fucking in mom's bed with her handsome, old boyfriend. After that first blow job, Ron was now mine to enjoy sexually just like my mother did. His big nine inch cock gave her lots of pleasure and I couldn't wait for him to put it inside of me, too.
I knew my mother's pussy was big because she used her big ten inch vibrating dildo in it whenever she didn't have a real cock in her. The first time she caught me taking her vibrator to use, she got upset with me. I told her I cleaned it good after I used it and I would buy my own jar of Vaseline to use, next time. But she was still mad at me in a jealous woman way. It was like I was fucking her boyfriend by using her big vibrator on my ass and she didn't want me doing it, anymore. But it felt so good inside of me, I couldn't stop. So, on the nights she was sucking and fucking Ron, I was sucking and fucking her big ten inch vibrator pretending it was Ron's big cock.
I wondered how my mom would feel, now, if she knew I was about to be fucked by her handsome boyfriend after he just filled my hot little mouth with a manly-size load of his cum. Would mom be mad that I was fucking her boyfriend like she was when she found out that I was fucking myself with her vibrating dildo in my ass? Little did she know I was fantasizing about her big handsome stud, Ron, while I sucked and fucked her vibrator, so I had already cheated with him in my heart. Now, I was getting him for real in mom's bed, all weekend long.
"Wow!" he said. "Gary's going to really love having you working for him, Courtney. You're as pretty as your mother and you're as sexy as she is wearing her underwear and you can give as good a blow job as she can. We can put her wig on you and lots of men will love having you sucking on them like your mom does."
I knew mom used to be an escort herself, but she had switched to being a mistress for a few rich men, instead. Ron became her weekend man and he offered to leave his wife for mom, but she told him she wasn't a one man woman. Her years of being a glamorous, upscale escort or lady of the evening made her desire the thrill of having lots of men wanting her sexually. They told her she should be a Hollywood movie actress and be a big star and their flattery went to her head.
She loved flying first class on airplanes and staying in four star hotels and eating in five star restaurants and shopping for expensive dresses to wear. And, of course, she loved all of the fun-filled fuck sessions she had with different men in hotels in Jamaica and Bermuda and New York City and Las Vegas and Paris. So, I was glad she had gone off on a fun-filled, fuck session weekend with her new boyfriend, a professional casino gambler, while I did her old boyfriend as good as she did.
"I'm glad you like my services, Ron," I said smiling widely. "And I can't wait to meet your friend, Gary."
"I bet he can't wait to meet you, too, Courtney," he said. "You're like a younger version of your mom and she's still hot as all get out, herself. I can probably have Gary come meet you, tonight, here. You can put on some of your mom's finger nail polish and lipstick and makeup and all. And her blonde wig. And I'll give him a call to come meet you."
It was so great to be told by my mom's boyfriend what to do as far as becoming her. I mean, he was the one who was attracted to her when they met and had kept coming back to see her every weekend, for years. Now, it was like he was my coach telling me how to look like her and be as sexy as she was. The thought of it was keeping my clitty dick hard down in her favorite black lace panties. I was glad they were dirty when she left. After smelling her cum-filled pussy scent on them, I jerked off on them uniting my cum with my mother's and her lover's, before washing them by hand. Now, her same little panties had captured her old boyfriend's attention and won his cock for me.
"That would be great, Ron," I said. "I'd love to wear makeup and a wig for your friend while he interviews me, tonight, for a job as an escort with his service."
"He'll want to do more than interview you. First, he'll want to see you naked. Then he'll want you to give him a nice long blow job, so he can make sure you can do it right. And he might even want to fuck you, too, to initiate you as one of his girls. He's bisexual, anyway, so don't be uncomfortable around him. Just suck him the way you did me, just now, and he'll hire you on the spot."
I said, "I think I'll tell him to blow his cum load all over my face though. That looks really sexy for a man and lets him feel in control like when he's fucking a girl hard. Men like to feel in control of a girl. And using their hard cocks to do it makes them feel extra manly."
Ron smiled at my young wisdom.
"Hey, you know how the game is played, Courtney. A whore is totally submissive and she feels useless unless she has a big cock to please with her lips and body. I think you'll make a good little whore boy. It pays one hundred and fifty dollars an hour, one hundred for you and fifty for the agency."
"Wow!" I said gleefully. "A hundred dollars an hour for me for doing what I love to do for as many men as I can already? That sounds wonderful, Ron."
I jumped up in his arms and kissed him like I saw my mother do so many times before. And when I did, I felt his softening cock touch my little asshole that was craving Ron's cock from my jerk off sessions with my vibrator already. The big head of it felt so wonderful touching the bottom of my ass cheeks while we kissed. This must be how great it feels for my mom and other horny women and girls, I thought. We need that cock between our legs so badly we'll put our big vibrator there if we can't get it. I had myself a trained ass from all the hours I spent fucking myself with mom's ten inch dildo.
Sometimes, I even left her dildo in me all night and I pretended I was spooning with Ron like my mom did after her long fuck sessions with him. I was so happy that the night was finally arriving when I could have his big cock in me and then spoon with him all night, too. Mom had lots of sexy underwear for me to wear for him all weekend like she did. Although her D-cup bras were too big for my C-cup titties, I was able to use padding to make my tits look bigger. Only being seventeen, my tits still had more years to bud out. But mom's garter belts, stockings, panties, thongs and G-strings all fit me perfectly.
It seemed I was meant to satisfy men's cocks ever since I put on my first pair of panties. They were a soft yellow nylon brief panty that made my cock throbbing hard and make me ejaculate more cum than I ever did before. The panties weren't my mother's. They belonged to my neighbor girl; a hot eighteen-year-old exotic dancer named Barbie who became my coach with becoming a girl and gave me her old bras and panties to wear. Now that I was seventeen, my hips were finally filling out enough to wear my mother's silky and lacy panties. Now, I just needed my tits to fill out like hers, too, and I would have as many men desiring me as she did. Ron was proof that I had her strong sex appeal in me, too.
My mother was a very sexual being. Not only did she like being fucked hard by men for hours and using her ten inch dildo for hours, too, she also fingered herself every chance she got. She would see a handsome actor in a movie on television and she would reach down in her panties and finger herself good right on the living room couch. Seeing her expressions of satisfaction when she played wither big clitty was a big turn on for men. So, I learned to make the same kinds of expressions myself while fingering my clitty dick. Now, I was using these expressions to turn on men while they sucked and fucked me.
You might say, my mother taught me how to pretend to be a good whore in bed. Now, I was ready to use the talents I learned from her to make myself one hundred dollars an hour as a high class tranny escort like she did. Her traits and her trade were passed off to me and I was happy to accept them and embrace her lifestyle as an elite call girl, the lifestyle she still loved even now in being fucked hard by her new boyfriend in Vegas. Whatever else I was meant to be was obscured by the sensual trappings of the paid courtesan I was raised by. I was becoming her "little me" and it was only now occurring to me since I was having sex with her old boyfriend and ready to go to work in her old profession, too.
I was realizing that I loved men's cocks as much as my horny, over-sexed mother did. And I was about to become as good at pleasing them as she was also, starting with Ron and Gary, tonight. I figured if I let Ron fuck my ass while I sucked Gary, the escort agency owner, and I made them both cum at the same time, I would definitely get the job. But first, I had to put on my mom's makeup, lipstick and her blonde wig and have more sex with her handsome boyfriend on her bed for hours, making the sheets all sticky with him like she did on weekends. Thanks for bringing him home for me, mom.
To be continued...
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/moms-old-boyfriend-part-one.aspx">Mom's Old Boyfriend: Part One</a>