Chapter 3 – Chapter 3

I didn't get much sleep that night.

I turned on the shower and looked at myself in the mirror as the water warmed. My hair was matted down from all of the cum that landed in it, and there was dried cum all over my face. My cock started to get hard as I reflected back on the evening of wonderful firsts: the first time at a glory hole, the first time jerking a guy off, the first time sucking cock, the first time swallowing… My hand instinctively moved between my legs and started stroking. The mirror began to fog up, signalling the shower was ready. I looked at the porn store shopping bag I had placed on the vanity and fished out one of the larger training plugs; while not intimidatingly large, it was definitely approaching the girth of a real cock. I pulled the bottle of lube out of the bag and entered the shower.

I backed up to the far wall, just out of reach of the shower spray, and leaned over, trying to gauge the best position for the plug. I pressed the suction cup against the wall and gave it a tug; it wasn't going anywhere unless I really wanted it to. I poured lube all over it, using my fingers to make sure it was covered completely. I bent over and slowly pushed back.

"Oh FUCK! I yelled as the tapered plug gradually spread me open. I took it nice and slow, listening to the signals my body was giving me. If I met too much resistance I added more lube and tried again, slowly inching it deeper inside of me until….

OHHhhhhhh!"

My cheeks slapped against the wall as the entire plug popped into me. I stood there for a moment, savoring the feeling of it filling me. I looked out of the glass shower door and noticed that the room's temperature had equalized so I could see myself perfectly in the mirror – bent over, ass pressed against the wall, my hard dick throbbing. I pulled away from the wall, then back…forward and back…slowly at first, then faster. I watched my ass fuck the toy in the mirror, my cock bouncing around from the motion, and imagined it was a stranger's nice hard cock I was riding.

"Oh yeah, fuck my ass!" I shouted as I bounced back against the trainer, my cock twitching as it spewed ropes of cum all over the shower floor. I finished showering, got ready for bed, and laid awake for hours dreaming about the night to come.

***

The morning was spent doing some more training. This time I used the largest toy which I had suction cupped to one of the chairs in the kitchenette. I was surprised by how quickly I managed to take it. I didn't want to make myself too sore, so after an abbreviated training session I got ready for the day and headed out to go shopping. I had no idea what I wanted to wear that night; I just knew I didn't want to go there in regular clothes. I drove down around the shopping district and passed by a store my wife and I jokingly referred to as the slut wear shop. It earned that nickname because they didn't sell anything even remotely modest. The growing bulge in my pants told me it was the place, so I pulled in to the parking lot.

***

The store was mostly empty, which did little to put my racing heart at ease. I had picked out two tight black skirts and I tried to covertly hold them up to see where the hemline would fall. The one in my right hand barely covered my ass and the one in my left hand came down to the middle of my thigh.

"Definitely the one in your left hand, and you should probably be looking at a large," a woman's voice called out from behind me. I turned around, my face flushed red, and saw a saleswoman approaching. She was probably in her mid- to late-sixties. Her long, grey hair was pulled into pigtails. Her platform shoes brought her height up to 5' 5", and that short frame packed a hell of a punch. She showed off her legs with fishnet stockings, her stretch skirt just short enough to reveal the tops of them and the straps of her garter belt. Her corset was proudly displaying her massive DD tits.

"Ummm, no, this isn't for," I stammered. She put her hand on the back of mine and pet it reassuringly.

"It's okay hon," she said, taking the skirt out of my right hand and hanging it back on the rack. "Believe me, you're not the only man who fills out part of his closet here. Heck, my ex shopped here regularly." She walked over to another rack of clothing and swapped out her preferred skirt for a large, grabbed a white corset top off another display, and handed them to me.

"Dressing rooms are in the back corner. I'll stand outside and make sure you have complete privacy." She made me feel completely at ease, so I didn't hesitate to walk back to the dressing room to undress and put on my outfit for the night.

"Are you going to Jodi's?" she asked through the door. I knew Jodi's held drag brunches on the weekends, and I thought I had seen flyers for "amateur night"…was that tonight? I admired my new outfit in the mirror before telling her no.

"You should go sometime. It's a really fun place! How do you like the outfit?" Feeling bold, I opened the door slightly and waved her in. She closed the door behind her and stood as far away as the small dressing room allowed.

"Turn around," she instructed as she looked me up and down. "Mmm hmmm, you look good. You do need some accessories, but this is a good start. When are you going to wear it out?"

"Tonight."

"Ah. If you'd like, I can come by tonight and get you ready. I have some ideas that will really bring this together." I was completely out of my element, and definitely welcomed any help I could get. She had a very disarming personality that made me feel completely at ease. She would be a perfect tutor.

"Ummmm…sure…seven o'clock?"

"I get off at six, so that's perfect," she said as I gave her my address. "I'm Joyce, by the way."

"I'm Greg."

***

I led Joyce to the family room, a large shopping bag hanging off her arm, her platform shoes clacking on the tile floor. She sat down on the couch and rummaged through the bag.

"Okay, first question: blonde or brunette?" she asked as she produced a blonde wig and a brunette wig in each hand. The brown wig was a short bob cut ad the blonde wig was long and flowing. "Blondes have more fun," she concluded before I had a chance to weigh in. She dropped the brunette wig in the bag and pulled out a package of sheer thigh-highs.

"We have some stockings and…some shoes. I guessed at the size. I picked short heels because I assumed you've never work heels before. Don't want you falling on your ass!" She handed the shoes and stockings to me and ushered me to the bedroom so I could get changed.

***

I was surprised by how aroused I felt when I looked at myself in our full-length mirror. I wasn't sure what the men at the porn shop would think, but I was definitely put in a mood to fuck. I walked down the stairs to the family room and Joyce flashed me a smile.

"Someone is getting lucky tonight!" she exclaimed, waving me over to one of the kitchenette chairs. Once I sat down, Joyce got to work: she applied some lipstick and eye shadow and worked tirelessly at getting the wig to look natural. Her tits were tantalizingly close to my face as she worked her magic, and I wanted to lift both our skirts up and fuck her brains out. "Maybe some other day," I thought as she put the finishing touches on me.

"There you go. So where are you going tonight looking so pretty?" she asked.

"Excitement Lounge and Video," I whispered sheepishly.

"Oh, that place can be fun. My ex and I used to go there often." She helped me to my feet and smiled. "Now the really important question: Thong or panties?"

"Commando," I smiled.

"That's the right answer!"

***

Joyce convinced me to let her drive me to and from the shop. I didn't know what it was about her, but I felt like she could get me to do anything she asked. The ringing of door chimes announced my arrival to the shop, and the men who had already assembled to "shop" turned towards the door. I flashed a smile and walked up and down the aisles, my cock stirring from the stares I was getting. I made my way to the back of the store and turned the corner that led to the back part of the building. A middle-aged man was about to enter when he heard my footsteps approach. He turned towards me, a tent forming in his pants. We locked eyes and his skin turned pale white.

The owner of the hard-on in front of me was my brother-in-law Brian. Of all the people in the world I thought I would bump into here, he would be the absolute last on the list. Not because he was married with kids, but because he and his wife Mary were devout Evangelicals. Gina and I would joke that her brother and her sister-in-law probably only fucked when they were trying to have kids, and even then it had to be strictly missionary position. Yet here he was, at a porn shop about to head into a room where men go to hook up with other men. I stepped closer to him and placed my hand on his crotch, my palm pressed against his hard-on.

"I won't tell Mary if you don't tell Gina," I smiled, giving his cock a squeeze, before moving past him and entering the back room. Brian, not surprisingly, followed me in. I led him to the sofa and turned him to face me. I slipped his pants and underwear down to the floor and was greeted by a fairly average cock. I grabbed his hips and gently guided him downward so he was sitting on the edge of the sofa. I lowered my head between his legs and took my brother-in-law's cock in my mouth. If my wife could see me now – on all fours, all dressed up, her brother's cock in my mouth. He leaned back and groaned as I slid my lips up and down his cock head. My skirt had hiked up, my ass and cock on full display. I pushed my head down and deepthroated him, the tip of his head barely reaching my throat.

I felt a pair of strong hands grab my ass cheeks, squeezing them before spreading them apart. A tongue swirled around my hole before pushing in and out, plunging deeply. I moved my head up and down my brother-in-law's cock faster and faster until I felt him explode an absolutely massive load in my mouth. I struggled to swallow it all, it was spurting so fast and furious. I lifted my head up, his soft cock flopping onto his leg, the shaft smeared with red lipstick. He slid off the couch and pulled his pants up and quietly slipped out of the room.

The tongue that was expertly probing my ass was replaced by the tip of a cock. I groaned loudly as it pushed inside, his hands still spreading my cheeks apart. He pushed in and out, going deeper and deeper, until he was all the way inside of me.

"Oh god yes," I groaned. I was amazed by how much better a cock felt than my training kit and I instinctively moved my hips forward and back, fucking his cock with my ass. His hips started to slap against my ass as we fucked faster, his grunts getting louder. As I was about to tell him to fuck my ass harder, a hand rested on my chin and turned my head to the side towards a rock hard cock.

"Mmmmm…fuck yeah," I whispered as I stared at the large head and the precum pouring out of it. The owner didn't even wait for me to open my mouth – he held the base of his cock with one hand, grabbed the back of my head with the other, and pushed his cock in. He was definitely bigger than my brother-in-law, and his head pushed against the back of my throat, making my eyes water. I couldn't help but gag as he pushed his cock in even deeper, the head sliding down my throat.

"Ughhhhnnnn," I heard someone groan as I felt warm, thick cum pour into my ass, his balls emptying inside of me. No sooner had he pulled out than another cock took its place. This cock was longer but with less girth, and his thrusts reached depths his predecessor didn't. He grabbed my hips and I let him direct the action, his hips thrusting forward and back, fucking my ass with the full length of his shaft. The viewing room was filled with the sound of another loud moan as the cock in my mouth started cumming. His orgasm wasn't particularly forceful; his cum shot poured out of his head more than shot out of it, which made it much easier to swallow.

His cock was replaced by two more, the owners pressing their heads together so I could suck them both off at the same time. I opened my mouth as wide as I could and they pushed both of their dicks in and out as my tongue massaged their heads. They didn't last very long, cumming all over my face, one after the other. Seeing my face painted by two cocks pushed the guy in my ass over the edge; he pushed all the way inside of me as he started to cum, his cock throbbing as he spurted inside of me.

My plan was to spend the entire night there, but after a few more hours I was utterly exhausted. Once there was a break in the action I texted Joyce to ask if she could come pick me up. I waited for her in the parking lot, my lipstick smeared, my face and corset painted with spurts of cum. She pulled into the lot and I slumped into the passenger seat and let out a deep, satisfied sigh. Joyce looked at me and smiled, running the back of her fingers across my cheek. I turned towards her and she leaned in and kissed me on the lips, her tongue slipping inside of my mouth briefly, before putting the car into reverse and pulling out of the lot.

***

"Would you like to come in?" I asked as Joyce pulled into my driveway.

"I would love to come in," she answered, kissing me again.

We barely got into the house before we started pulling each other's clothes off, We backed our way into the family room, kissing each other passionately, She pushed me back on the sofa and mounted me, my cock sliding effortlessly inside of her. She bounced up and down on my cock, her huge tits swaying as she rode me like a bucking bronco. She threw her head back and orgasmed, her pussy juices flowing all over me. I followed soon after…my balls finally getting relief…my cock erupting inside of her, filling her with my cum.

She crawled up my body and straddled my face.

"Eat your prize like a good boy," she said as she lowered her pussy to my mouth. I dutifully licked and sucked on her pussy lips as my cum oozed out of her and into my mouth.

"Mmmmm….good boy…" she cooed as she fed me my cum.

She slid down my body and lay on the couch next to me.

"Thank you," I whispered to her, kissing her on the lips.

"My pleasure."