Couples Only: Glory Hole Night Ch. 03

I arrived home, started the coffee and jumped in the shower to start my day. I dressed and sat down at the breakfast table to drink my coffee and read a magazine. Joe joined me a few minutes later with a smile on his face. I inquired and he told me set us up for a date tonight. When I asked who, he grinned broadly and said it was the blond I was with during the party. I beamed, knowing today was a whole lot better.

We went to the gym later that morning. I worked out hard and even joined the aerobics class already in progress. Joe and I hit the sauna and I was able to reflect on what I was doing and what I going to wear. We talked about the upcoming date with the sexy blond who fucked me (and whom I fucked later that night) and her boyfriend, Chris. Oh, he also told me the blond haired girl's name was Jill. Of course, they expected me to be dressed as a woman and I admit I knew the conditions of the date the moment Joe told me that morning. I amazed myself that I realized I had no problem with the arrangement. Sure, I was going to be a gurl again and I was eager for the moment. The sauna felt good then we hit the showers and headed home.

We did not do much until I had to get ready. I shaved first, then showered, then shaved again, then took a scented bubble bath. Afterward, I laid my clothes out on the bed and thought about each item; how they would fit, what they would look like, how sexy, and how passable I would be.

The clothes are the hardest decision as a woman. Dressing as a guy is easy: slacks and buttoned shirt, comfortable shoes. I knew I, as Dawn, needed to do better than slop on a dress and wig. I ultimately chose the light brown dress to compliment the beige shoes, since I did not buy other shoes yet and I did not want to wear the same shoes the first time I met, and had sex with, the hot blonde. The brunette wig was all I had at the moment so I laid that on the bed with the dress and shoes.

I rummaged through my recently purchased clothes, thanks to the sexy sales guy, and settled on nude pantyhose (not the pair with the large rip. I kept that one as a memento in the drawer.). This pair of pantyhose was only thigh high and required garters and belt to keep them upright. Pair that with the light brown bra and panties and brunette wig, and I think I did okay. I knew if I wanted to continue my cross-dressing I would need a real woman's help in the future. However, I was content for right now. Of course, I added the adhesive breasts to ensure I had a 'true' c-cup visage to the collection and my outfit was complete, splayed on my bed.

I practiced for two weeks putting on make-up but tonight was the real deal. I took my time painting my toes and nails first. While they dried I studied make-up applications on the internet so I would look as good as possible. I did my best with perfume, blush, lipstick, highlights, the works. In front of the mirror, I smiled, sulked, grinned, opened my mouth wide, chuckled, batted my false eye lashes, winked, and any other expression I could dream up so I knew what I looked like and how I wanted others to perceive me.

I checked my voice so many times over and over again. I talked to my mirror. Softly speaking to it and then raising my voice and then lowering my voice. I wanted to know the right pitches I wanted to achieve so I would sound like a woman. I would say regular sentences, then more provocative sentences, then coo and ooh and all other sounds I could think of uttering during sex or normal conversation. I spanked my cock when it rose too high and tried my best to maintain my excitement. After talking to myself a little longer, I decided I was as good at this moment as I would today. Perhaps later I could be better but right now I was comfortable with my female inflections.

I carefully put the brunette wig on me, adding pins where necessary, and dressed to impress. I checked myself out a thousand times in front of the mirror before I was comfortable enough to step out of my room to greet my roommate, Joe. I guess he heard me walking toward him. Wooden floors would always give me away when I wore shoes and I had to force myself to remember this slight problem in the future. You can's sneak up on someone with women's shoes on a floor, I registered. I saw him look at me with a beautiful expression on his face.

We would have kissed but he understood I did not want to ruin my appearance. I felt him genuinely embrace me as a man would greet a female lover. He gushed over my appearance and when I spoke he complimented me many times over how unbelievably sexy and beautiful I sounded. I don't think he was granting me lip service and I gobbled up his compliments with the lust and circumstance we were now involved.

Joe explained we were going directly to their apartment and showed me he already bought the alcohol since I was taking so long to get ready. He was quick to apologize if he offended me before I said a word. I loved the attention, the concern, and his thoughtful attitude toward me. Joe was nicer and more attentive to my needs then I ever experienced in any person.

We entered the taxi and drove to their place. The ride was not as uncomfortable or weird as the first or second time we rode together with me in drag (The first and second times were the rides to and from the glory hole party). Joe and I had nothing, really, to prove to one or the other. There were no misgivings this time. We held hands driving to our mutually agreed upon destination and no false pretenses were fooling us.

We were friends, very close friends for a long time, and almost comfortable in this type of situation, given our recent exploits. However, we were definitely excited about the possibilities that neither of us would have ever dreamed had I not agreed to dress for him. I understood I was going to have sex with a man so Joe could fuck the woman I laid three weeks before, albeit under different circumstances.

Chris and Jill greeted us at the door warmly and led us inside. The guys drank beer and Jill and I drank the wine and we all shared small talk. After a little time passed with us talking about nothing, Jill excused us and took my hand to lead me to their bedroom. I girlishly waved to Joe and dutifully followed Jill. Inside their room, she simply gushed how beautiful and sexy I was and how wonderful my voice sounded.

"So," she excitedly asked me, "How long have you been with that hunk?"

"Um, we are roommates," I shakily responded.

"You mean you haven't fucked?" She asked incredulously.

I shied away but nervously answered, "He fucked me once, for the first time, a day after the party. I loved it!"

"Have you fucked him yet?" She eagerly asked me, holding my thigh as we sat on her bed.

"Huh? I did not even think about it." I answered, confused, not ever thinking I would want to fuck him.

"Girl, you have to think about it. You have to understand the power you have!" Jill said, tightening her grasp on my leg. "You can own it and anything else you want. You are fucking gorgeous!"

I shuddered while listening to her. She was the beautiful and sexy one. She was outrageous and daring and sexy. I was just a wannabe-something-I guess. Though, I knew I had a hint of power. I knew I could seduce or be seduced by someone easily enough. I just wasn't as cute, pert and fuckable as Jill; and I told her so.

"Honey," She said and caressed my leg. "You are more than you know."

I blushed deeply and tried to respond.

"Trust me," She said, patting my thigh. "I want to have a little fun with your boyfriend and you have fun with Chris. Believe me though when I tell you, that you will have your friend's very cute butt cheeks between that heavenly hard clit of yours before the night is over."

I giggled and hugged her.

She picked up her pocket book and we greeted the two men in the living room. She turned to the stereo and put on some smooth jazz music. The men refilled our drinks and Jill was gently swaying to the music while we watched her sexy body dance seductively. She took my hand and we danced with drinks in hand while Joe and Chris watched the slow seduction enthusiastically.

Jill eventually took my empty glass of win and eased both glasses on top of the coffee table and the dirty dancing was soon underway. With my back to the guys, she leaned into me, grabbed my ass cheeks in both hands and I nervously cupped her ass. Her fingers inched up my dress to show off the tops of my stockings, the garters, then the bottom of my panties were revealed to the admiring eyes of our men. She held the dress up with one hand and the other was gently swatting my ass to the pleasure of our excited male audience.

My dress was off me before I knew it and Jill turned me to face them while she held me captive. I was nervous as she held my arms and pushed me lewdly at the waist; mimicking fucking me. The guys went wild and I ate it up and even showed them my 'oh my god, the cock is so big and I am enjoying getting fucked' look.

Chris took this moment as his cue to move forward and pull out his already hard cock. Jill let me go and I instinctively knelt on the ground and grabbed Chris' pride and joy. I licked and sucked the tip while he pulled his pants down and removed his shirt. He held my hand roughly in his hands as he face-fucked me at his pace. I was not complaining. His cock was big, thick, and dripping delicious precum.

I heard the moans from the couple nearby. Joe was getting his wish as I heard the two of them ripping off clothes and the slurping of man and woman. Chris turned me around and pulled my panties to my knees and I watched the other couple in a scintillating sixty-nine position. Jill was on top and sucking his cock while Joe noisily sucked her pussy, parting her lips for deeper access.

I was on all fours as Chris lubed my ass and put on a condom as I excitedly watched Joe and the ultra-sexy Jill get it on. I lost my breath when I felt Chris' cock head push into my ass-pussy. He was so fucking wide I almost cried out in pain. Jill had turned around and dropped her pussy on Joe's cock. She rode him like a cowgirl as Joe squeezed her tits. I felt tears run down my cheeks as Chris shoved his cock deeper inside me. Jill was thrashing around and humping quickly and screaming loudly. Chris squeezed my ass cheeks together as he fucked me slowly then quickly picked up the pace.

"Oh, fuck! That feels so good!" I finally admitted to myself and everyone else in the room. "Fuck meeeeee!"

Chris fucked me even harder. A few strokes later and I was on my back, holding my legs up, as his thick fuck-stick continued to pummel my ass-pussy.

Joe was banging Jill from behind, as she knelt on all fours to watch her boyfriend fuck me.

"Let's switch!" Jill exclaimed.

She pushed off of Joe and attacked Chris, winking at me and nudging me to Joe. She ripped Chris' condom off him and plunged her pussy on his rock hard, thick, gorgeous cock. I took the lube and a condom from the coffee table and crawled to Joe, who had collapsed to the floor. I am sure he thought the condom was for him but I watched his eyes grow wide as I knelt before him and unraveled the dick protector onto my extremely hard clit. His eyes were alternating between the sexy couple fucking and watching me preparing my dick for his ass.

He remained on his back, with eyes darting back and forth, as I applied the lube to his ass hole. I was so excited I was going to be the fucker and he was going to be the fuckee. I could only imagine what he was thinking as this wannabe broad with the false set of tits and fake hair, but fabulously sexy person, was about to inject seven inches of pulsing meat into his body.

I smiled sweetly at Joe when I touched my cock head at his anal opening. I had his full attention when the head pushed past the rim of his asshole and my shaft slowly followed. I felt him wince and I was slow to ease inch after inch inside him at a measured pace, pausing before each slight push of my hips. He held fast onto my ass cheeks as if to halt my actions but we both knew I would not stop until all of me was inside him.

I finally felt my balls pressed against the cheeks of his ass. He moaned, though I hope in pleasure, as I slid a few inches out of him, then slowly pressed until I was once again fully inside. He moaned again and I repeated my actions a little faster. Each time I would pull out further, only to push deep a little quicker. Eventually, his resistance ceased and I was able to grasp and stroke his cock as I pumped in and out of him in equal tempo with my firm grip on his manhood.

"You go gurl! Fuck him good!" Jill burst out between gasps as Chris pumped in and out her pussy.

I tried to see her but was too enraptured with my own fuck partner. Joe and I were soon screaming out as mutual orgasms racked through our bodies. I came into the condom as I watched Joe's sperm shoot out his piss slit onto his chest and oozing over my fingers. I collapsed onto his body and pressed my lips to his as our cocks softened.

We slowly parted and watched Jill and Chris through their orgasms. Chris was taking her doggy-style so they could both watch us fuck. Our cumming set them off and Jill moved forward to reward Joe with a pussy filled with Chris' sperm. He was reluctant so I dove in and ate her to my heart's content. His cum seeped into my mouth with every swipe of my tongue against her pussy lips. I was soon tongue fucking Jill to get more cum and urged her to cum again and again soaking my lips and face.

I easily led Chris to the floor to join the entanglement of bodies. There were kisses, feels, gropes, and laughter as we came down from the wild experience.

We dressed and Joe and I had a drink for the road while we waited for the taxi. I was hugging next to Chris and Joe was relaxing with Jill until we had to go. We said our goodbyes and I was not letting Joe hide from me. I encouraged him to have his way with me on the ride home. I enjoyed making him cum with my hand in his pants while the driver watched my hand job through his rear view mirror.

I was insatiable and I loved it. Joe reaped the rewards the following week and the week after. I bought a few pairs of new shoes from the cute salesman. And yes, he did eventually fuck me and I loved it. I found out Joe had a shoe fetish and I loved to show off my new purchases and enjoyed Joe's cock in me several times with me naked except for a pair of shoes and stockings. I bought a new wig and other gurly things and I have sex with men and women; dressed as a man or a woman. My success rate is phenomenal, if I do say so myself.

-- Eve had been plunging the vibrating plastic cock in her so many times and she had so many orgasms by the time Dawn finished. She was drained physically and emotionally. The recliner was totally soaked with female cum. Dawn, for her part, thoroughly enjoyed watching Eve's masturbation sessions and was eager to join her but wanted to wait for the main course.

The soft padding of wet feet on the floor made Dawn and Eve smile widely. Their prey was near. --

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Hi All. I hoped you enjoyed reading the story as much as I did writing it. Please vote and comments are always welcome. Feedback, good and bad, are always welcome and encouraged. I love to read them. Thanks!