Glory Hole Part 1
By Leigh_216
Hi, I am Leigh, a Crossdresser (CD), Caucasian, 68″ tall, women’s size 8 or 10 depending on the brand, green eyes, and shoulder length hair. I have always had soft facial features. My stories are more of a diary entry than a novel. They actually happened but I changed the places and names.
I’ve been really curious about glory holes. It started innocent enough as I looked into stories and I watched a few videos online about them but I could never just go and try it. That is until I met Bob in a chat room. Bob works at the adult bookstore near the airport and I spent many evenings chatting with him listening to all his stories. Bob is a nudist, a voyeur as he enjoys watching and being watched, and on top of it all he has a nylon fetish, not wearing them, he likes “feeling it” on other people’s body let’s say. After about a month Bob was almost ready to meet me.
Almost ready to meet me, in that he wanted me to meet with one of his friends first to see if I was the real deal. I guess this will be ok, I mean there are a lot of people that fake some or all of their online identities. Well whomever I’m meeting will be impressed I hope.
I wore a short tweed skirt and jacket outfit over a black leotard with a pair of leather mid-calf boots over dark nude pantyhose. I looked more like I was going to a job interview than an interview for sex. I was given an address to a condominium south of the shopping mall on the Far East side. The last eight or so messages from Bob was reminding me how important secrecy was in this meeting.
I knew I wasn’t meeting Bob at his place, I was in a suburb about forty-five minutes from the airport. I parked in the visitor parking near the dumpster, as instructed, then I climbed the flight of stairs to the condominium. When I got to the door I stopped in shock at the name on the door bell [REDACTED].
The [REDACTED] family owns a gun store and an orchard. They are kind of a big name in this area and they worked with the company I worked for so naturally I was scared this was someone I knew from my regular job. I was nervous and I wanted to run and get the heck out of there but I didn’t, I rang the bell. A young man answered the door, well not that young he was younger than I was by a couple of years. He smiled at me and I explained Bob asked me to stop by.
With a big smile Ryan invited me in. Ryan was really nice and acted really happy to see me. He reminded me of this jock guy that went to my high school, I confess I had a secret crush on him maybe that will work in Ryan’s favor today?
The main room of his condominium was a long open space with a kitchen near the entrance and a sliding glass door leading to the balcony on the other end. I was a little confused, the condominium seemed to have a woman’s touch and it wasn’t your typical early American Bachelor Feng Shui. Curtains, all the furniture matched, corner china cabinet filled with Princess glassware, I wondered was a wife going to drop by and surprise us.
“Wow, you look amazing”, Ryan beamed, “can I get you a drink?” he asked as he invited me to sit on the couch.
“I have to admit I looked at your pictures in your profile and honestly, I thought they were faked.” Ryan admitted as he made us a couple of drinks.
I accepted the drink with a smile as he returned, I was sitting knees together at a slight angle as he settled in next to me.
“You’re not bad looking either” I confessed, as I sipped my rum and coke he made me.
Ryan was wearing a brown and orange checkered button down shirt with a brown football helmet over the pocket and nicely fitting jeans sporting a handsome bulge in the front.
We sat and chatted and drank a few more rum and cokes. I’m not sure when it happened or what we were chatting about before it happened but Ryan leaned in and kissed me and I kissed him back. Before you knew it we were making out like teenagers.
Ryan had his right arm around my back and his left was feeling up my boobs. I slid my hands up his leg and started exploring the bulge in his crotch.
He stopped and looked at me. His lips were pink from my lip gloss, he smiled and invited me to go to the bedroom. “Yes” is all that I could say.
Entering the bedroom I felt a little more at ease, this was truly a bachelor’s bedroom. “Stuff” was all over the place and the bed wasn’t made. I sat on the edge of the bed removing my boots and my blouse while Ryan retrieved a bottle of lube and a condom from the dresser near the foot of the bed.
I helped Ryan out of his shirt and I unzipped his jeans and undid the button. I pushed his jeans down exposing his black spandex boxer shorts. I slid my hands over the softball sized bulge he was sporting. I liked how smooth his boxers felt and something was stirring in that bulge.
Ryan sat next to me on the edge of the bed and began kissing and biting my neck, I continued to rub my hand up and down his cock and balls through the spandex boxer material. He pushed me back and began sucking on my left nipple. I wasn’t use to it and I had to concentrate to let him nurse on my tit like that. Odd, a little uncomfortable, and electric all at once. When he was doe we kissed some more.
Ryan stopped kissing me and stood at the side of the bed in just his boxer briefs with his hands on his hips and a shit eating grin on his face.
“Um, excuse me mister but didn’t you forget something?” I asked.
Ryan looked perplexed. “You sucked on my right boob but not my left, I think you need to even things out.” I insisted.
Ryan pushed me back and went right to work, like a good boy. He really gave it a work over then resumed his stance at the side of the bed. I slipped off the edge of the bed and onto the floor kneeling in front of Ryan.
It’s a very erotic thing to be on your knees in front of a man. You know his cock is going to slide into your lips and try to deposit its seed deep into your throat. I love that involuntary roughness near the end that men exhibit, it’s so animal and honest.
I could tell Ryan was getting worked up, he was moving his bulge closer to me so flashing him a coy look I took the hint and started peeling his boxer briefs down his thighs exposing the most beautiful uncut cock and some of the largest balls I’ve seen to date. As if his cock knew I was there it started swinging towards my face as it kept me memorized by its thickness. Ryan moved forward brining the tip of his still growing cock closer to my lips.
I was compelled to kiss the tip of his cock, it twitched in anticipation to what was going to happen next. I licked its length then I leaned forward to lick his balls while I hefted them in my hand, my other hand on his thigh for support. I looked up and Ryan was smiling, I took that as approval to continue.
I took his cock in my mouth and swirled my tongue around the tip, by now his cock had grown to an impressive eight or nine inches. I licked the top for a few moments before making a tight seal on the head of his cock with my lips and allowing it to slide into me. Past my lips, onto my tongue, I allowed the head of his cock travel back into my mouth until his cock head began rubbing the roof of my mouth near the back of my throat then I rocked my head back sliding his manhood back out. I sucked on his cock so it would make a loud pop when it came out.
I giggled and sucked his cock back into my mouth like I was sucking a milkshake through a straw, his cock was nice and thick and understandably rock hard. I pumped my mouth over his cock intent on giving him the best blowjob ever, I assumed this was a blowjob interview, pun intended.
I took him by the wrist and placed his hand on the back of my head and grabbing his ass I encouraged him to thrust his beautiful cock into my mouth at his speed, not necessarily mine.
This took very little effort to feign distress as Ryan’s cock started fucking my mouth, his hands pulling my head towards him and his hips thrusting his cock into my mouth occasionally going too far back into my throat causing me to gag. My gagging seemed to make his cock even harder as he increased his thrusts and the amount of precum I had to swallow was making this challenging.
“You are a beautify cock sucker, did you know that?” Ryan grunted in rhythm with his thrusting hips.
I could only look at him, his hands and cock were keeping my head immobile. His cock was sliding across my tongue and the roof of my mouth almost at the same time. It was surreal watching his stomach moving towards my nose then away from me, he was fucking my mouth, he was using my mouth, and I loved it. The feeling of being used but even more I loved he accepted me for who I was becoming.
Ryan pulled his cock out of my mouth, leaving me there on my knees trying to swallow and wiping the tears from my eyes from the mouth fucking he just gave me.
“Are you ok?” He asked. I could only nod that I was ok, my voice wouldn’t come out.
“Good, dam you mouth felt great, the guys are going to love coming inside that pretty mouth of yours Thursday night.” Ryan said.
“I was good enough?” I asked in feigned surprise. Come on who ever had a bad blowjob?
“Turn around and put your knees on the bed, head all the way down and ass all the way up.” Ryan commanded. Ryan quickly found the hook snaps in the crotch of my leotard then peeled the nylons from my legs.
“I thought this was a blowjob interview, didn’t you want to cum in my mouth?” I asked.
“I actually wanted you to cum in my mouth.” I confessed.
“I’ll fuck and impregnate your mouth Thursday night, I promise. Right now I want some of that righteous ass you have here.” Ryan said.
I do have a nice ass, the hormones I started have helped but forty-five minutes a day every other day on the elliptical helped a lot. Ryan started kneading and kissing my ass cheeks. Slowly and methodically, one cheek then the other.
“This is one great ass.” Ryan explained.
“Thanks” is all I said. Then Ryan goosed me with a lubed finger then he started a come here motion with his fingers pulling out to add lube. His finger felt ok but I knew that cock of his was going to be a lot bigger. Ryan moved me forward on the bed and came up behind me. I reached behind me to stroke his cock, he moved my ass to the height he wanted and then positioned himself behind me. I could hear him applying lude to his cock and stroking it a few times before he slide the head of his cock between my cheeks. I was about to get fucked.
The head of his cock pressed against my opening, it was like a bowling pin was resting against my ass trying to force its way in. Ryan was already pushing really hard and I anchored my body with my arms to keep from sliding across the bed then finally his cock popped inside of me. Pain radiated through my hips and Ryan’s cock continued to push into me, momentarily pulling back only to push further inside of me. I moaned in pleasure but mostly pain as he continued to push inside.
“Fuck your ass feels great, I love this ass” Ryan moaned.
Ryan pulled my shoulders towards him as he pushed the last couple inches of his cock into me. I felt his hips on my ass and knew he had fully mounted me, right now Ryan owned me and he could do anything he wanted and I loved that feeling.
Ryan held my hips and started to fuck me, slow then building speed then slowing down. Soon the pain dissipated and I was able to enjoy the cock inside of me, it really started feeling good and I let Ryan know.
“You cock feels amazing inside of me.” I purred while I carefully rocked my hips.
“You like my cock inside of you baby?” Ryan asked.
“I love it I said, I want your cock deep inside me.” I said
Ryan pulled all the way out, then he slammed back into me. Then he did it again, all the way in as soon as he pulled out. The head of his cock was hitting my entrance, forcing its way in then pushing all the way inside in seconds, Ryan continued fucking me this way. I made an involuntary squeak noise every time he plowed into me. He was pushing me across the bed he was fucking me so hard. I think the noise I made as he hilted me encouraged him to speed up. I opened my eyes and the open bedroom window was right there. I remember a couple walking across the parking lot and she was giggling knowing someone was getting lucky tonight.
He fucked me hard for at least another 30-minutes before he stopped, his hips pressed hard against my ass, I could feel his cock pumping his seed into the condom inside of me. Ryan pushed down on me and rolled us to the side, his cock still inside of me, occasionally I thought I felt it twitch, pumping one last drop now and then. After a minute I felt his cock slip out of me but he lay there and he held me until we fell asleep.
TO BE CONTINUED…