Bored Stiff 10
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DISCLAIMER: This is a fantasy depicting sexual acts involving male teens.
The story is intended for adult readers and not minors. IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE. All characters are fictional and in no way related to any person or persons living or deceased.
Following nephew Jeff's demonstration of new skills on his uncles fat dick we both rested and refreshed a little before heading out to the store intent on starting a lingerie wardrobe for our newbie sissy, Jessie. On the way I told him to relax as I sensed his nervousness going to a public place and cruising thru the lingerie department. I explained a few things. First with the limited travel stuff going on there would be a small amount of other shoppers to see him and second having to keep a mask on would conceal his identity anyway. Plus I reaffirmed how `boys and bras' friendly Paula was. She had managed that department for a long time and I was super comfortable not only shopping there but in asking for her assistance in deciding what to buy.
Stepping off of the escalator lingerie was straight ahead. Paula smiled when she saw me and welcomed us both. "And who is this fine specimen, Claire?"
Jeff might have been a bit surprised that she knew my alternate name. "This, Miss Paula, is Jeff and sometimes Jessie. My roommates nephew who is visiting and after some very comforting experiences already this week he would like to start a collection of more feminine garb."
Paula was mid thirties. Long shapely legs that stretched way up into the finest ass ever stuck in a skirt. It was hard not to notice as the hem length she typically wore showed a lot of thigh and drew everyones ogling eyes right to it. Could not stop there though as the shimmering satin material of her blouse, taut across her well endowed chest, gaped a tad giving Jeff and I both a teasing peek at the lacy garment keeping her perky should I say. Jeffs gaze was fixed on her chest as we continued talking.
"So, boys or ladies, shall we start with some measurements and go from there?" Paula made a tape measure appear from a nearby drawer.
Getting all the numbers we followed her into the jungle of nylon, satin and lace that was the lingerie dept.
Thumbing along a rack of bra she lifted one out on the hanger, held it up to Jeff and asked what he thought.
"Do you think you would like to try this one on?"
Visually flustered while trying to stutter out an affirmative response, Paula rested her hand on his shoulder with a casual rub to calm his fears. Her hand then slid down his back so her fingers engaged with his current bra band. Giving it a tiny tweak, just enough for the tension sensation to bring him out of his stupor, she gave it a snap.
"Well i guess that answers the question. Yes you want to try this on."
Still mute, Jeff followed her like a little puppy, me trailing them both, while she snagged up a few hangers of possibly coordinating panties on the way to the dressing room. The one with the real door instead of a curtain. "You will be so private in here. I had it put in especially for the crossdressers and sissy boys who have come to enjoy shopping here. It locks too and has plenty of room for two. Heck maybe three. You slip into these and I will be back with more suggestions to fill out your wardrobe."
In the room I sat while nephew boy newbie, still kind of gobsmacked took off his shirt and pants putting them on the hooks while he slithered into the purple panties Paula had offered. I jumped in to help him get the matching lace pushup bra secured in the back with shoulder straps perfectly positioned as they would appear in a catalog. Nice.
Jessie related before the mirror taking in every detail of the cup design, lace trim, underwire placement and how nicely it, and the panties, enclosed him. We were both starting to chub up our frillies when Paula returned with a half dozen of everything. Panties, bras, slips, garter belt, camisoles, and even some stockings for the newbie to try on.
I think Jessie was ready to pass out from the emotions of it all. Getting the many thrills of sexy, silky feminine adornments piled on all at once. He sat on the bench while Paula hung up the new stuff and assured him again that everything was fine and to relax as she checked the fit of what he had on already.
As she began the process she suggested that he see how a bra should fit. "Why don't you get my blouse unbuttoned for me before you melt a hole in the satin with your stare. That touch of lace in there gets you going. Huh?"
As she thrust her chest towards Jessie he fumbled, almost helpless, with the buttons. His eyes as big a saucers as her full gorgeous breasts, tantalizingly enclosed in peach lace cups, suspended with wide lacy straps, came into unobstructed view.
"You are all hard now aren't you sissy? Seeing my amazing tits fire you up? Or is it the super sexy bra. I bet you wish you had tits like these don't you? Finest ones money could buy", Paula giggled looking over at me.
I knew her story. Born a boy but not that comfortable with the role growing up. She got into wearing her sisters undies about the same age most of us did, fifth or sixth grade. Built a collection early by rummaging thru friends family laundry baskets that always seemed in close proximity to the rec room or pool table in the basements. Sexy soft undies became the norm for Paul, later to become Paula.
After high school she decided it was time to switch gears and start living as Paula full time. She transformed her entire closet to skirt, dresses, panties, bras and all under things feminine. Trying hormones failed to give her the lovely full breasts she so desired so she saved her money and got implants. Now she was almost all girl and loving her life.
Back to Jessie. Paula palmed his chest giving those pecs a firm grasp and the hardening nipples a slight twist. Jessie purred.
"Some day you might have nice ones like mine." She took his hand and put them atop her fabulous orbs. " Go ahead. See what great tits feel like. Yeah, pinch my nipples. Good girl."
Paula was right in front of seated Jessie, making him work her tits and knowing that his horny feelings were ready to burst. He would do anything she asked right then. AT this point wearing only her bra, a short skirt and stockings that i could tell were the lace top stay up type. I did say her skirt was short, right?
"I'll wager that you are as hard a a brick in your pretty purple panties right now and Claire over here is too I amp very sure." She moved closer to Jessies face while his hand continued to explore her chest as demanded. With her blouse hanging loose from her shoulders she told me to get it off of her and hand it up.
"Gently you prissy slut. Be respectful of my finery."
Rising and standing behind our fabulous sales girl I did as i was told then unhooked her bra as well as her wink suggested I do. She lifted Jessies mitts from her front as I gently removed the garment and then she placed them right back on the bare smooth pinkish orbs encourageing his play time.
Paula questioned jessie. "So sissy, you doing ok?." He nodded.
Paula went on. "Look Jessie, you are hard as a rock, Claire is hard as a rock." Putting her hands to the hem of her skirt she stunned our young newbie with "Guess who else is hard as a rock?" Raising her skirt above her waist and thrusting her sheer pantied crotch against Jessie's face, she yells, "Me! I have a raging hard on and you need to make it go away and earn the friends and family discount for your purchases today!"
She held the young mans face firmly to the wide long tube of true-gendered meat that was already dampening her smooth panty front. More like the side as she was that long. Easing the pressure allowed Jessies lips to cradle that column of cock while Paula swayed left and right. His lips traced the penile profile again and again as the tip side of the panties got wetter and wetter.
Paula looked over her shoulder at me and inquired "Do you think she wants so of this down her throat?"
I nodded. Our new little cock slut was hungry for a big one and pushed down her panties and literally stuffed the entire pillar of prick into the now drooling hole that was Jessies mouth. All the way. So thick it was that Jess gagged and sputtered awhile. Paulas hands on the wall over the sissy's head braced her solid allowing a slow deep in and out plugging of cock meat into the newbie throat. Him bursting with spit mixed with all of her precious and delicious precum was getting Paula even more excited. Me too.
Again looking back at me." Well don't just stand there sissy bitch. Get on your fucking knees and service my fine ass like you know you should!"
Dropping like a run away elevator my knees hit the floor tongue extended ready to go. Lowering her panties further fully exposing Paula's pert and perfect bottom, my thumbs split the crease using a firm grip to spread the warm buns and poke the pucker. Damn her ass was always so sweet. She must be the worlds best butt douch customer. I could not stop exploring that tight tush. My spear like tongue doing the job she wanted done while she face fucked Hanks nephew in the front.
I reached thru her legs to manhandle her balls and stimulate her taint as Jessie took about a mile of oozing meat thru his tongue teasing tunnel while making joyous slurping noises. He even managed a number of its-so-fucking-good comments in the moments he was allowed to catch his breath, peppered with I-love-sucking-cock here and there as well. Lucky little slut. Rimming Paula was great but I was getting so horny for cock in my face.
As tight as I was holding her ass pussy while I ate it, she thrust forward off of my tongue to bottoming out in Jessie's throat. My hand still engaged in nut tossing under there felt the massive surge before Jessie was flooded with a stupendous splattering shaft of hot spooge. The pressure so great and his sucking and hungry mouth not big enough to handle it, the eruption of a viscous Vesuvius began, The vast majority of out flowing cum lava covered his chest and saturated the purple bra forming a cleavage reservoir of hot glop.
As Paula's pulsing penis required pulling out it continued to blast gonad gravy all over our young sissys sweet face once again giving him the glazed donut look.
Our sales girl mistress told him to gather all the goo from his chest and face and "eat it like a good girl".
With her big slime slickened boner whipping thru the air, she turn to me on my knees and told me to clean her the fuck up. Ah, finally cock in mouth today and a thick, hot sloppy one as well.
When we recovered and all the clean up was accomplished. Pauls told Jessie she had earned the Friends and Family discount as well as the "I guess I came all over them" freebie of the purple bra and panties saturated during the "fitting" session.
While putting herself back together I explained to Jessie all about the presence of a huge cock on the otherwise oh-so-feminine girl. "When Paul moved to swapped genders she initially wanted to go all the way.
After the not effective hormones moving her to get those beautiful breast thru implants she considered the other surgical conversion. Having a stable of boyfriends, and a few girlfriends, whom had enjoyed the pleasures of penetration her fat phallus provided, they talked her out of it.
Paula chimed it while rebuttoning her shiny blouse, sadly for us, taking her bra wrapped boobs from our jealous views. "I realized that at that point i had the best of both sides. All the holes I really needed and I loved throat fucking all my lovers of whatever gender. I would have so missed covering my fans in the hot sticky cum they desired as well."
"Jessie, my loving little cock sucker, try on the other goodies. What ever fits well bring it all to the counter so I can check you out, with your special discounts, and wrap it all up pretty. Kind of like you came in here- All wrapped up pretty.
Jessie tried on three more bras by himself while I fumbled to get my still hard sissy dick back in my tight panties. I assisted a bit with the hooking. Told him I would help getting him trained to do it himself before he went back home. The camisole looked gorgeous after drifting down his bra encased chest.All of them were nice and the bottoms Paula had suggested were superior to behold on Jessies fine butt. He opted for the patterned stay up stockings without unwrapping them and passed on the one garter belt that was suggested.
All back, neat and proper , in a manly way again we hauled it all to the register. Layering each carefully folded item with pink tissue, the large dress sized box was quickly filled with Jessies new ensembles. Paula had wisely put the cum soaked freebies in a plastic sack that I casually hand carried away after swiping my credit card. Young sissy Jessie, now in possession of the proper attire, proudly carried his bulging box of treasures .
Cant wait for the modeling session for his uncle later that evening.
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