True Story, Bi-sexual, Blowjob, Cum Swallowing, Erotica, Exhibitionism, First Time, Group Sex, Hardcore, Male / Older Female, Masturbation, Oral Sex, Role-playing, Threesome, Transsexual, Water Sports/Pissing
In my story MY GYM BUDDY'S STEP MOTHER, I related how when I was twenty-one Jillian, my gym buddy’s step mom seduced me.
“We are way past SEX 101, way past,” Jillian told me. “Would you like to pursue even more erotic levels of sexual pleasure with me and some of my friends? Perhaps males and females? Do you have any special requests while we search for new levels of sexual pleasure you would like to share with me?”
After many months as Jillian’s mommy’s boy she still finds many new and exciting ways to sexually excite me. One day I entered the bathroom naked, to shower, while she was about to pee. “Stay there John, you can watch mommy pee. Would you like to watch mommy pee?,” she asked as she opened her legs and commenced peeing without waiting for an answer.
“Mommy’s kinky boy likes that doesn’t he? So do I, pleasing my kinky boy. I have never given you a golden shower, something I should have done for you, and for me long ago. Come into the shower with me I will give you your first golden shower. I assume it will be your first?”
“Stand with your back to the wall while mommy concentrates. Mommy is going to give you a golden shower, pee over your groin. Count to five slowly for mommy, help me concentrate,” she whispered softly, standing two-feet away, legs slightly spread, hands on her hips, thrusting her almost bald pussy toward me. The exquisite look of sexual pleasure on her face one I had never seen before.
“One, two, three, four,” I counted slowly to build the tension and excitement for both of us, me especially. Before I got to five mommy commenced squirting a long, steady stream of warm amber fluid over my groin and now rock hard erection, groaning, “Oh wow, oh fuck,” as I enjoyed my first golden shower. A new level of foreplay for me, before we showered together, then another round of wonderful, exciting sex.
In the afterglow Jillian told me, “Mommy would like to introduce you to some more of her girlfriends. Next time two of my girlfriends. You could fuck one of them while I watch. While you watch me having lesbian sex with the other. Have you ever watched two women making love, having lesbian sex? Would you like that? Could you handle that John?”
Alexa and Allegra were very exciting for both me and mommy. Alexa was a very attractive, though almost obvious lesbian, slicked back blond hair, little make up, slacks and low heels, her and mommy very comfortable with each other, making it obvious they wanted to have each other.
Even at my young age I almost immediately recognized Allegra as a cross dresser, fascinated by him as I admired his feminine appearance and clothing. Wanting him to have me while mommy watched. Undressing a cross dresser for the first time in my life, and enjoying my hold over him at that moment.
His black silk short first, a beautiful firm pair of tits, I couldn’t resist licking and sucking his nipples. Then his skirt over his heels, with his back to me. Hard to believe his gorgeous ass in a sexy black garter belt with stockings was a male ass. Then turning to face me, his good size erection a huge turn on for me, framed by his garter belt and stockings.
Then Allegra undressing me. The first time a male, has undressed me. Even more exciting when that male was cross dresser. His soft fingers and hands caressing my nipples as her removed my shirt. Mommy and Alexis watching as he slid my trousers past my ankles, my erection rock hard for them.
I had never had my balls licked and kissed by a male before then. So good, what have I been missing? His collagen lips smeared with lipstick were an extra turn on as he left smudges of lipstick on my erection after he commenced working on it.
He was rolling my balls around in his hand while he sucked my erection. Focusing on my balls with his mouth, a hand working on my erection as he licked all around my balls with a broad, flat tongue. Taking each ball in his mouth for a a few seconds, licking between my balls, while Alexis and mommy watched. My cock had never felt quite like this before. So good.
Lots of lube, my erection glistening with it. Using his hands, twisting his wrist back and forth as he moved up and down. His other hand teasing my balls. Talking dirty to me, flattering me, telling me, “I wanted to do this to your beautiful big, thick cock the moment I saw it.” Asking me, teasing me "Do you like how this feels? Or this?”
Teasing and edging me. Using his tongue to stimulate the head of my erection. Moving his mouth up and down my rock hard shaft. Deep throating me, taking as much of my erection far as he can, reaching his throat. Licking, sucking and chewing my nipples.Licking my inner thighs, scratching my ass.
Teasing me. Edging me. Not rushing, prolonging my pleasure, making me wait for the orgasm he wants me to have. Teasing me by touching and running his tongue along my erection.
Kissing and stroking my body, expertly masturbating my erection. An orgasm like no other before, with Allegra and mommy watching. Then Alexis and me watching Allegra and mommy making passionate sapphic love, lesbian love.
Two weeks later mommy told me, “I have invited Leslie to visit us next Sunday, you know I have a thing about cross-dressers.” Mommy had a huge self satisfied smile as she showed me some pics on her screen. “He is ten-years younger than me, with an awesome body. Would you be comfortable watching me having oral sex with Leslie? And he me?
“Would you be comfortable having oral sex with Leslie? More importantly, would you like to have oral sex with Leslie? Would you like me to watch? Would you be comfortable having a three-way with him? Have I turned you on with my questions? I hope so?”
“I would be very comfortable having oral sex with Leslie,” I smiled, my new bi-sex curiosity aroused as I carefully scanned the pics. Leslie was very attractive and ultra feminine. Shoulder length brunette hair, a very short dress displaying his wonderful thighs, with his good tits hanging out of the dress. Leslie has piqued my interest. I am already aroused at the thought of sharing him with mommy.
On the Saturday afternoon mommy had her legs over my shoulders as I slowly tongued fucked her with her magnificent ass cheeks in my hands. “Would you like me to give you blow job after this?,” she teased as I had her on the brink of her second orgasm. “Or do you want to be extra horny for Leslie tomorrow? You know I want to watch you with Leslie. And you know I want you to watch Leslie and me.”
“A blow job while you tell me why you want me to watch you with Leslie,” I moaned.
“I want you to watch me seduce Leslie,” mommy whispered as she was providing a wonderful blow job while I fantasized about watching her seducing Leslie. “He has a wonderful feminine body,” she teased as she sucked the just the tip of my cock and simultaneously provided an extra, wonderful dimension of sexual pleasure with her tongue.
“And I want you to watch me give him a blow job. And I want to watch him giving you a blow job,” she teased as I was on the brink of orgasm. “Would you like that? I think so,” she teased some more.
“Yes, yes, swallow, now,” was all I could mutter, so turned on by my impending orgasm and mommy’s requests.
Always very exciting greeting a third person for the first time for our mutual sexual pleasure. Mommy and me are both exhibitionists and love flaunting our naked or semi-naked bodies for our guests, male or female. As the cliche goes, you only get one chance to make a first impression, so we always take great trouble with our appearance and dress.
I decided on the macho look, low cut, skin tight slacks and asked mommy to oil my torso, hoping that would be a turn on for Leslie.
“Do you think this outfit will appeal to Leslie?” Mommy asked as she chose a very feminine look. Heels, no knickers, and a skimpy, sexy black cup-less bra as I helped her on with a short, black cocktail dress. “Does my ass look big?, she asked as she lifted the skirt.
“Your outfit appeals to me, it is a turn on for me and you know your ass looks big, it is big, absolutely magnificent. I love it.”
“Wow, you are a very pretty boy Leslie. And kinky apparently,” mommy told him as we looked him over and he us. Just as I suspected and hoped, Leslie was not an obvious cross dresser, though a most attractive one with a shapely feminine body with a tucked in waist. Just the right shade of lipstick, his gold loopy earrings, floppy black felt hat, black knee length skirt with killer heels, black stockings and a black silk blouse were very appealing for me.
Wonderful sexual tension as mommy whispered, “I told my boy I was going to seduce you Leslie. I have his permission,” before she tongue kissed him and he returned her kisses. “We are going to enjoy you, both of us,” she whispered with two hands holding his face as she continued tongue kissing him.
The only clue to his real sexuality was the way he walked with heels, not natural, and his deep voice when he spoke for the first time. “Is that a promise, both of you? I have been looking forward to pleasuring and being pleasured by both you. Both at the same time, an erotic menage.”
His soft fingertips on my torso, then lips and wet tongue on my nipples were incredibly arousing before mommy continued kissing him before she helped him remove his blouse to show us his good, firm tits.
I was very comfortable licking and sucking one of his very feminine, large nipples while mommy did the same to the other one.
“My skirt would look better around my ankles John, do it for me,” he whispered as mommy continued licking his nipples while I undid the zipper to slide his skirt down to his ankles.
“Oh fuck,” mommy and I whispered as one as we ogled his very large, beautifully shaved, almost hairless, erect cock, framed above his stockings and below his sexy, skimpy black garter belt as he posed hands on hips for us. He had incredibly feminine legs and thighs, even his taut ass was very feminine as we both watched him enjoy teasing his erection with a fingertip for us with a look of sheer sexual pleasure on his face.
“Does my outfit appeal to you Leslie? Does my ass look big?,” mommy teased as she turned her back, before I lifted her dress to flash her naked ass for Leslie. “When showing a new man or new lover my naked body I always feel sexier in heels, no knickers, and a skimpy, sexy black cup-less bra,” she smiled as I helped her off with her dress as Leslie and I ogled her almost naked body.
The way Leslie slowly licked and kissed his way down my torso was something new and exciting for me while I looked down on his tits. The way he licked me with his wet tongue and kissed my torso just above my low cut, skin tight slacks as he teased them down past my erection, then to my ankles was very erotic while mommy was tongue kissing me.
The sensation of his tongue and fingertips teasing my balls as mommy continued tongue kissing me was exquisite. Then his hands, then his tongue on my erection was electric with mommy watching before he placed our erections together for comparison.
Mommy’s face was flushed with sexual excitement as she passionately tongue kissed me while Leslie commenced licking, then sucking my erection. “So good mommy. So fucking good,” I moaned, any doubts about another man, albeit a most attractive cross dresser, giving me a blow job had completely vanished.
“This is our sexual pleasure chair Leslie,” mommy told him as he settled in it facing a wall length mirror.
“You are very exciting for both of us Leslie,” mommy whispered moments before she passionately tongue kissed him, her hand on his erection, just as she had done to me.
“You are a big boy, a very big boy,” he whispered as I teased him, and myself by sliding the tip of my very erect cock over his nipples.
“You are very exciting for both of us Leslie, my boy loves to watch,” mommy repeated as she licked the underside of his erection. “My boy really does love to watch,” she whispered, one hand teasing his balls, as she glanced at me, the sexual pleasure on my face obvious, the moment she slid his erection between her pursed lips.
“Oh fuck yes, yes, yes, I want it now, now,” was all I could manage to mutter as Leslie grasped my balls and slid my erection between his wet lips. The way he used his tongue at the same time was absolutely magical while watching mommy excelling herself with her blow job skills.
Entirely new levels of sexual excitement as I watched my lady giving an incredibly attractive cross dresser a blow job while he was giving me a blow job.
Leslie was mimicking mommy. She would stop to tease him while she stroked his erection. Leslie would do the same to me. “Keep on blowing my boy while I watch. Now watch me blowing Leslie, both of you.”
I had my hands behind my head, soaking up the double sexual pleasure, a hung, very talented, tranny giving me an exquisite blow job, while I watched my lady doing the same to him.
“Nearly there mommy, nearly there, watch me, watch me,” I was groaning as I fought to hold back my orgasm. I wanted mommy to watch Leslie bring me off. He was expertly teasing my erection with his loosely closed fist. Then just the tip of it with his fingertips.
“So good, so fucking good mommy,” I was almost screaming, breathing heavily, my body shaking with mommy watching as she did the same to Leslie.
It was a week later after Mommy told one of her friends about our encounter with Leslie, when she asked, “Did your man reciprocate with a blow job for Leslie? Was he tempted?”