Bored Stiff

By Lacy Lips

Published on Jul 9, 2023

Transgender

Bored Stiff 7

©Lacylips@gmail.com

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.


Hank had headed off to his room and it was time for my `beauty sleep' as well. Entering my room to find young Jeff slipping into a red nylon speedo. His clothes were neatly folded on top of the dresser we were now sharing and plain old white jockey briefs lay on the laundry basket beside it.

"You going swimming Jeff?"

With an embarrassed look he said. "No but I like to sleep in these. I love the feeling of the silky cool material against my parts and sad to admit but I love touching myself in them too. I wish that I had pretty panties to wear like yours but none of my moms stuff is at all interesting. I did snag one of her old slips that I love to jerk off in though. I bet you understand those feelings."

"Ah, Yes I do. Maybe there is some sissy in that teen body that wants to come out? How about you ditch the swim suit, reach into the third drawer there and pick a pair of dainties to slip on for the night?"

Without hesitation he briefly explored the drawer and my collection within then extracting a lovely pair of white nylon high leg cut briefs with a tiny pink bow in the center of the waist. Holding them in front of himself with both arms extended his excitement was obvious. As he brought them to the floor, inserted his legs and pulled them up his stiffening prick was also obvious. This was getting good.

"Clint, these feel so so good. Thank You. I love how they feel. So tight and smooth." His hands were exploring the tented surface as he spoke. In awe of the sensations even his breathing accelerated as his face flushed a bit. Maybe a new sissy was born?

"You look rather cute in them Jeff. Hot and hard. I guess you have found a feeling you like in the underwear department. Give me a second to dress for bed myself." I left the bra and panties on and just lost my shirt and pants exchanging them for a bright fuchsia satin chemise nightgown that was so short it merely brushed the waist of the hip hugger bottoms.

Meanwhile Jeff was in a trancelike state turning and moving watching his reflection in the mirrored closet door. Seeing himself in his first prissy look was taking over his psyche. Now was the right time to ask.

"Do you want to add a bra to your ensemble? Jessie. I think dressed like that deserves a feminine adjustment to your name. Agree?"

His eagerness to continue could not be hidden. "Heck yes, Jessie is ok and where are the bras. I cannot believe I am doing this. Can I sleep in here. I don't want uncle Hank to see me like this quite yet. Pretty please?"

"Of course. It's a big bed. Plenty of room. One drawer down, under the t-shirts is the bra department if you really want to try one on."

Like a fisherman thrilled to see his fits catch on the line, Jessie's eyes lit up dangling a blue satin bra with white lace upper cups from his middle finger. His breathing was staggered in anticipation of actually donning the gorgeous sexy garment. I thought he might pass out.

As he stood statue-like, kind of frozen in space, I took the bra from his hand, had him extend his arms and slip into his first brassiere. Moving behind I connected the hooks making sure everything was neat and proper. With a reach around I positioned the cups. His well formed pecs fit in quite nicely and my stretching and adjusting of the shoulder straps added to his no-way-he-could-hide-it delirium of sissy dress up.

I was pretty excited to see Jessie like this as well as demonstrated by my stone state pantied erection pressing into his fine nylon covered bottom while I tweaked the bra for him.

Stepping back to check my new creation, sissy Jessie, I asked. `Ready for bed sweetie?" He answered by climbing into the far side and getting under the covers. Seeing his lingerie adorned body and his tenting cock in shiny nylon had me diving in as well.

We were both on our backs enjoying the coolness of the fresh sheets I had put on that afternoon, with just the sheet pulled up over us. Jessie rolled a bit on his side towards me and asked if we could talk, like confidentially, he said. I assured my new bed buddy I would keep anything he said to myself if he wanted.

"Should I call you Claire?"

" Clad in this array of dainties I think female names for both of us are proper."

As he began the conversation his hand found its way to my chest.

"Ok" he asked.

"More than OK. Please continue, your hand and your concerns."

Jessie cupped my bra supported man boob allowing his fingers to dance over my hardening nipple. There was an air of cooing in is voice while his hand massaged by pseudo tits thru the satin of the nighty and lace of the bra. I told him how nice it felt and urged him to continue telling him that I loved having my nipples pinched. He did just that a few times on each side before his hand came to a stop just below the band.

"Claire. I don't know where to start this. I am embarrassed to say that I love how I feel right now in the bra and panties. I have pictured this in my mind for so long but with no sisters I have not had a chance to test the waters in the female clothing I find so enthralling. Lingerie catalogs have been my jerk off motivation for years but it has only been mental pictures of me dressed this way that got me going. Thank you."

"Jessie, I am glad you are enjoying this. I understand your feelings as they are very much like my own at your age. I was lucky to have a sisters stash of undies to draw on and a friend, Bobbie, who understood me desires and accepted them. I was his `girl friend' for a few years before he had to move. Think about this afternoon and you know what I missed most after he left."

"Sucking cock and eating cum?"

"Bingo. We have a winner! Oh sorry I interrupted you."

"Well on the subject of sucking cock. When I told uncle Hank about my virginal state and desire for a blow job I think he misunderstood me. I went nuts with your talented mouth sucking me off and watching you suck Hank as well. At that point I could not tell him that what I really desired was to GIVE a blow job. I have craved the idea of sucking a hard cock and having my face and mouth plastered with hot cum ever since I found sissy porn on the internet. I love the taste and feel of sperm in my mouth and have not wasted a drop since I was 12. I want cock though. The idea of a fat hard dick in my mouth overtakes my thoughts all the time. Makes me crazy."

My head was reeling with Jessies admissions of his deepest desires. Hearing them was thrilling as well. My pecker was trying to rip its way out of my hip hugger bottoms as I sensed his hand had moved lower and now rested directly on my fully swollen cock.

While his fingers traced the profile of my hardness I opted to take a chance on being in charge. "Suck my cock Jessie! Push my panties down and get your fucking horny sissy mouth all over my dick. you know you want this. Go ahead. Suck cock, bitch!"

He eagerly raised my nighty, put his hand inside the panties and brought the waistband to hook under my nuts. Seemingly in one motion, as his hand performed the adjustment to my undies his lips made contact with my oozing dick and his tongue slathered and slurped at the precum puddle that had appeared. I guess he did love cum based on his enthusiasm to get it started.

Jessie repositioned to kneeling between my legs and completely removed the silky garment hindering his access to my balls. I instructed him how to grip my glass like penile pole while working the baby batter filled nuts with his tongue, pulling at the sack with his lips and taking each testicle into his very wet mouth for a cleaning like a ball washer at the golf course. He was very good at all of that for a newbie.

I could not wait any longer to feel his young lips sliding over my turgid tool. I gave him the word to begin a slow tongue powered lick up the shaft from my well dampened scrotum to the precum glazed mushroom head and to make sure it was properly buffed before taking my entire dick into his sissy mouth pussy. I have no idea of his internal reaction to the rather kinky instructions but his actions told the story as he ascended the length, polished the sweet gooey tip and stuffed my entire pecker into his mouth. It touched his throat and he gagged forcing him to pull off a little.

"Don't try to take too much your horny slut. Back off and get that fucking fag tongue to work. I need to cum and fill your face to fulfill your fondest desires!"

He got busy real quick. Wanting him to get a full and extended experience of giving his first blow job, I often told him to squeeze the base of my cock very tight. "Keep it in your mouth cocksucker but no tongue or pull my dick out of your sweet face and softly lick the big cock you so desired all over. Keep the grip firm so I don't cum yet. You do want more cock right?"

Jessie nodded as the meat left his warm wet orifice and he began a sensual slathering of my shaft accompanied by lots and lots of spit. Oh I love it sloppy, giving or getting. Gloppy is great!

As he neared the bottom and his chin dragged over my tight nut sack and swollen balls I instructed him to keep going. "Sissy bitch. Do you know what taint is?"

He shook his head. "Well slut, It ain't balls and it ain't asshole, so it's taint. Flick that talented tongue over my taint for a bit. In another lesson I will allow you to tongue fuck my sweet sissy ass but right now you have a big load of cum to generate so get after it!"

He gave it a try. Again, newbie level but not bad. The long slow lap at the base of my ball sack was an extra thrill and I complemented him on the technique.

"Drop the grip bitch, It is almost time for your cum face anointment. Proceed directly to cock in mouth."

Yeah he did that with no hesitation. Just in time too as the second my cock head cleared his moist sucking lips I unloaded. The massive geyser of goo coursed up from my boiling balls and almost took his head off as the full force of the streaming pillar of penile puke hammered into his throat. He hung in there but I gripped his head and pushed away enough for him to get a bulging mouthful of sticky delight to savor instead of a direct to stomach throat injection. I so filled Jessie up! Memories of my earlier enjoyment of the same condition overtook me as the lava like flow from the corners of his mouth began. So much fucking cum. Hot, gloopy, slippery, musty goo soon battered my crotch and balls as he fought to contain it all. Did not work.

Force by the pressure to pull out, my still pulsing prick graced his face with white streams of dripping goo giving my newbie his first glazed donut look. Jessie was exhausted and fell over unable to finish the clean up tasks that sissydom required. I gave him a break using a slip in the bedside table as a cumrag before neatening my nighty, rolling away and going to sleep.

Not sure how long Jessie was out for but the sun had not appeared before the young pussy boy was whispering in my ear to straddle him and fuck his face. Not a bad wake up call. Right?

Comments?

lacylips@gmail.com

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Next: Chapter 8


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