After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours.

Not only had I actually sucked a man’s dick, and let him fuck me, but I had loved every minute of it and couldn’t get the thought of doing it again out of my mind. It seemed I was having something of an identity crisis. Was this the real me? Could I really be a cock craving sissy slut? Had my life until now been a lie? I never considered myself a real ladies man. I’d been with plenty of women over the years and loved sex with them, or thought I did at least, but sex with them had never given me the kind of thrill I felt when Jack bent me over the bed and entered my virgin hole.

In my state of confusion, I turned to the internet for help. I searched out others like me. I read articles and studied forums looking for answers and advice. I settled on one particular site that seemed helpful and welcoming. Before long I’d met others there that I came to consider friends, though we’d only chatted online. Through their kind words and advice, I was able to accept this new version of myself. I also learned several new tricks to make myself more feminine in looks and mannerisms.

True to his word, Jack returned the Sunday following our first encounter. I watched through the kitchen window as his wife pulled out of the driveway and left for church. Moments later, Jack emerged and hurried across the street to my door. He wasted no time, taking me in his arms and kissing me forcefully on the mouth. He carried me to the bedroom, tearing my lacy panties off before ravaging me. If there had been any doubts in my mind after our first encounter, there were certainly none after the second, I was definitely Jack’s girl now.

From that point on, every Sunday his wife’s car would disappear down the street and Jack would hurry across the street to fuck his girl. And his girl couldn’t have been happier. For the next three months that is. Then Jack zipped up his pants one Sunday afternoon and announced that would be his last visit to my bed. He was worried that we were going to get caught. In a small town like ours it’s hard to keep secrets for long, and if this secret got out, things would go very bad for both of us. Jack just wasn’t willing to risk that any longer. I understood perfectly his reasons; he could lose his wife and friends, practically his whole life. Still, I couldn’t help feeling hurt and abandoned.

Living in a small town as I do, my options for finding another lover were extremely limited. As a result, I spent more time than ever on the forum, chatting, role playing, and satisfying myself with a growing collection of toys. I dated women, occasionally, and even slept with a few, but I really needed a man to make me his girl again. Relief came quite suddenly and unexpectedly.

On a Thursday afternoon, nearly a year after Jack had put an end to our Sunday afternoon playtime, some major problems cropped up with a project I had been putting together for more than a year, and I had to make an unexpected trip to Denver in order to find a solution.

By the time I arrived in Denver, checked in to my hotel and grabbed something to eat, it was late and I was tired. I flopped on the bed with my laptop. After checking my e-mail, I logged into the forum to unwind before going to sleep. I checked into the chat room for a bit and was about to log out when Jerry logged in. Jerry and I chatted nearly every night. We worked in the same field and had a lot in common. Jerry was a nice guy and we chatted about everything including his desire to fuck a cross dresser. Our chats often got both of us hot and stroking ourselves to orgasm.

As I greeted Jerry, a chill ran down my spine as he told me how tired he was because he had to take an unexpected trip to Denver and had only just checked into his hotel. I immediately knew this was no coincidence, and after a few more questions my suspicions were confirmed. I knew Jerry, he worked for one of the subcontractors on my project. We had never met in person, but we had been talking on the phone almost daily for more than a year. I was in panic and didn’t know what to do. Jerry knew all about me, I had told him things I had never told anyone, feeling protected by the anonymity of the internet. I didn’t know what to do. I needed time to think. I told Jerry, since he was so tired I’d let him get some sleep and logged off.

I was exhausted, but couldn't sleep. Jerry knew all my secrets and had seen pictures not only of me dressed as a woman, but pictures of me with a large dildo stuffed in my ass. Luckily my face had been obscured in all of the pictures. If he said anything to any of my coworkers, I was done.

I started considering my options for employment after I was fired. Then I realized, I also knew Jerry’s secrets and had pictures of him as well, granted none of him wearing panties or riding a large dildo, but still damning enough. I felt a little better with that thought in mind. Besides, I figured out who he was, but revealed nothing for him to figure out who I was.

The next morning I met Jerry face to face for the first time. He was taller than I expected with broad shoulders and muscular arms. He had a handsome face, but his best feature, by far, were his deep blue eyes. When he looked at me and smiled, I felt a strong urge to fall to my knees and worship the wonderful cock that I knew was hidden within his jeans.

Throughout the day I struggled to focus on work as I recalled all of the naughty chats we had shared. Several times, I caught myself glancing at his crotch, remembering the pictures he had sent of his thick hard cock. By the end of the day, it had become clear that Jerry and I would have to return home for the weekend then return to Denver on Monday in order to figure out a fix for the problem. Luckily, we got along as well in person as we did in the chat rooms and on the phone and my fears from the previous night had turned to thoughts of revealing myself to Jerry and hoping we could do a few of the things we had chatted about.

As we ate lunch together, I felt perfectly comfortable, as though I were with an old friend, not someone who I’d only met face to face just that morning. I almost confessed then and there, but I was unsure how he’d react. I imagined he’d be freaked out, just as I had been the previous night. By the time we got a cab and headed to the airport, I thought I had come up with a good plan and held off telling Jerry. We had a drink together at a bar in the terminal, then said goodbye and parted ways.

On Saturday night, I logged into the chat room and set my plan in motion. After Jerry and I had chatted a bit, I typed:

“If we had the opportunity, would you want to get together for real, or is this just internet fantasy for you?”

I hit return and waited anxiously for his reply. It took a while for him to reply and I thought I had my answer, but then his reply popped on screen,

“Yes, I would love to meet in person if we could. I’ve always just considered this online fantasy, but chatting with you has made me want to live out my fantasy more than ever.”

Reading his reply sent a thrill through me, causing my cock to twitch in my panties. This was it, time to fill Jerry in on what I already knew and hope he was being truthful in his reply. If not, the next week was going to be extremely awkward, for both of us. My hands were shaking as I typed,

“Jerry, we have already met in person, and we will both be in Denver together all this week.”

I swallowed hard as I pressed the return key.

This time Jerry took even longer to reply. I waited nervously, imagining all that was going through his head at that moment. I was starting to wonder if I had made a mistake when his reply finally came.

“Holy shit! Shaun? How long have you known?”

I explained how I’d discovered who he was on Thursday night and why I hadn’t said anything sooner. We spent most of the night discussing our coming week together and the various things we might do together. My panties were soaked by the time we logged off.

I was so turned on as I searched through my outfits, choosing what I would wear for Jerry, I had to stop packing for a session with my favorite dildo, which I judged from the pictures was about the same size as Jerry’s cock.

I arrived in Denver just before noon and dropped my bags at the hotel on my way to the project site. I could hardly concentrate on work as my mind was continually occupied with thoughts of the evening’s planned activities. Jerry would be arriving on a later flight and should be at the hotel by the time I got there.

I left work a little early and raced back to the hotel to get ready. I was so excited to have a man in my bed again, I couldn’t shower and shave fast enough. The hard part was not rushing through the application of my make up. My skills had improved greatly with tips and advice gained on the forum, but I still needed to take my time to get it right. With hair and make up done, and wearing red stockings with a red G-string, garter belt, and matching bra, I stepped into my tight leather mini and red silk blouse, then texted Jerry my room number.

Jerry must have sprinted to my door as his knock came even before I had stepped into my heels. I checked myself in the mirror before opening the door and inviting him in. A hungry smile covered Jerry’s face as he looked me over.

“Damn you look good, Shauna.

It’s nice to finally meet you,” he said, stepping through the door and kissing my offered hand.

“Thank you, it’s so nice to finally meet you too, Jerry,” I answered, making my voice as feminine as possible. I pushed the door shut and ran my hand lightly over his bulging bicep. “Make yourself comfortable while I pour us a drink,” I said, hoping I sounded as sexy as I thought I did.

I poured each of us a stiff drink and joined Jerry on the small sofa. He seemed a bit nervous as we sipped our drinks and made small talk, but the obvious bulge in his jeans told me he wanted he was enjoying things so far. I shifted closer so our legs were touching. Jerry placed his hand on my knee and turned toward me.

“You really do look amazing, even better than your pictures,” he said, his eyes roaming down over my body.

“You look great too. It’s nice to finally see your face,” I replied, leaning closer and running my fingers along his cheek.

Jerry smiled and kissed my fingertips as his hand slid up to the hem of my skirt. My heart beat faster and moisture began to collect between my thighs. Jerry leaned closer and our lips met as his fingers reached the top of my stockings. My lips parted for his strong tongue to slip through and my flesh began to tingle where he touched me. I reached for his bulge and gasped into his mouth as I felt his hardness. It felt much bigger than it appeared in the pictures.

Jerry’s kissing grew more insistent and his hand slid higher. I stroked his hard member through his jeans as his advances forced me to my back. He rubbed the wet spot on my panties, causing me to moan. He took possession of my mouth with his oral onslaught and his finger searched out my boipussy. I fumbled to open his jeans as his finger traced my opening. Jerry sat up, breaking the contact between our lips and stared down at me, lust evident in his eyes.

“Let’s move to the bed,” he said, pulling his shirt over his head to expose his broad hairy chest.

I took a moment to catch my breath and watch Jerry as he kicked off his shoes and pushed his jeans down from his hips. I sat up, smiling as I reached for the waistband of his boxers. I tugged his shorts down, gasping as his thick hard shaft sprang free. It was definitely longer and thicker than it looked in the pictures he’d sent. I stared in wonder, wrapping my fingers around his magnificent member and stroking it from tip to base. Jerry’s eyes fluttered shut and he groaned as I smeared his slick precum over the wide purple head. Jerry stepped back, pulling his thick tool from my grasp and sat on the bed.

“Your turn baby, show me what you’ve got,” he smiled a lascivious smile.

Getting up from the sofa, I concentrated on making my movements as feminine as possible and sauntered toward him, slowly opening my blouse. I slipped the blouse off my shoulders and ran my hands over the lace cups of my bra and slowly down to my skirt as the garment flattered to the floor. I could feel Jerry’s hot breath on my exposed flesh as I reached for the zipper at the back of my skirt. I turned slowly as I lowered the zipper. With my back to Jerry, I slid the mini down from my waist, bending over and pushing my ass out as the skirt slid down my stocking covered legs.

“Ohhh gorgeous,” Jerry breathed, placing his hands on my smooth ass.

Warm tingles spread through my body as his hands caressed my cheeks. His hands moved out over my hips and down the outside of my thighs as I felt his warm lips touch my ass. His teeth lightly grazed my flesh as his arms wrapped around my waist. He pulled me onto his lap, kissing his way up my back as his hard cock slipped between the cheeks of my ass. He lightly bit the back of my neck and his fingers pinched my nipples through my bra. I leaned into him and moaned as I wriggled my ass on his stiff cock.

Jerry twisted to the side, laying us down on and once again slipped his finger into my pussy. I turned my head and reached back to pull his face closer so we could resume kissing. Our lips locked and our tongues twisted together as Jerry slipped a second finger into my tight hole. I rocked my ass on his fingers as our kissing grew more passionate. I moaned into Jerry’s mouth as he stretched me with yet another finger.

“Damn you’re hot,” Jerry gasped.

I reluctantly pulled away from Jerry’s magic fingers and pushed him back with a hand on his chest. “I want to taste you,” I breathed, reaching for his swollen member.

Jerry rolled on his back as I gripped his hard shaft and caressed his large balls. He was dripping with precum and I savored the taste as I licked him clean. Jerry let out a loud moan as my lips enveloped his thick knob. I inhaled his musky scent as I held the knob in my mouth, swirling my tongue around and over it before taking him further into my mouth. I began moving up and down on his shaft taking it a little more at a time.

With practice, I had been able to swallow all of Jack’s cock, but it wasn’t as long or nearly as thick as Jerry’s. I concentrated on relaxing my throat and breathing through my nose as the thick knob began to invade my throat. Jerry was leaking profusely and thick precum coated my mouth as I took it deeper and deeper. Jerry almost shouted as my lips finally reached the base of his cock. He grabbed my head as his hips bucked and he exploded deep in my throat. Spurt after spurt of hot cum shot straight down my throat as Jerry thrashed about on the bed. I had been concentrating on taking all of Jerry’s thick rod and wasn’t expecting him to cum. I came up choking and gasping for air.

“Oh, that was amazing!” Jerry panted, pulling me to him.

Kissing me hard, he rolled us over, smothering me with his hard hot body. His strong hands were everywhere,caressing my body as he kissed my face and neck, and ran his hot tongue along my collar bone. Peeling my bra down, he took my stiff nipple between his lips lightly scraping it with his teeth. I gasped at the sensation, and squirmed beneath him. His finger once again found my puckered hole, swirling and teasing it as his lips moved lower.

Jerry sat back, looking down at me with hunger apparent in his eyes. “Mmm baby, you are so hot. I want to lick your hot pussy,” he said breathlessly.

I melted under his stare, wanting him to do anything he wanted. “Ohhh yes, eat my pussy, please,” I pleaded.

Jerry’s fingers twisted in the waistband of my G-string and tugged it down exposing my wet swollen clitty. I lifted my legs back, spreading them wide to display my smooth boi-pussy for him. My breathing quickened and I trembled with anticipation as Jerry lowered his face between my legs. He kissed my swollen clit and drug his hot tongue over the tender flesh between my legs down to my needy hole. I moaned and began to squirm as he swirled his tongue around my tight opening. His hot tongue lapped at my hole before pushing its way inside.

His tongue felt so good inside me. I had never been eaten before and I let out a long low moan at this new found pleasure. Jerry’s hands roamed over my torso as he fucked me with his hot tongue. I pulled my legs back further, moaning as his hot tongue made me squirm. Jerry stopped Licking and moved up between my spread legs to kiss me.

“You ready for my big hard cock in your tight pussy baby?” he asked, his voice a low growl.

The urgency of his kiss spiked my need to be filled. “Yes yes yes, please, I need your big hard cock in my tight pussy,” I moaned, running my fingers through his thick nest of chest hair.

Jerry’s lust filled eyes stared down at me as he rubbed his thick knob over my opening. He pressed forward and I felt myself opening for him. I arched my back, breathing out as his thick tool stretched me. I winced a little as my pussy was stretched farther than it had ever been. I began to get a little scared as the pain increased, but then his thick knob slipped inside and it felt wonderful.

“Oh yes, fill my tight pussy,” I moaned, pulling Jerry down for a kiss.

His strong tongue invaded my mouth as his hard shaft completed its incursion of my tight hole. Our lips and tongues twisted together feverishly as Jerry began pumping his hips. His thick rod stroked my needy hole, taking my breath away as pleasure rippled through me. Jerry began fucking me with long powerful strokes that rocked my body.

“Oh oh oh fuck, fuck me fuck me,” I called out as he pounded me.

“Oh fuck your pussy’s so tight,” Jerry grunted.

Jerry grabbed my ankles, pushing my legs back further and drove his hard cock into me harder and faster. The same way he had taken possession of my mouth when we first kissed, he now took total possession of my body as he drove his thick hard cock into me over and over.

Sex with Jack had always been tender and sensuous. He always took his time, slowly building to orgasm. This was so different. Jerry was filled with passion and need. There was a raw urgency in the way he was taking me, and my body was burning for him.

“Oh God baby, I’m gonna fill your pussy with cum,” Jerry grunted as his hips slammed into me.

“Oh yes fill me. Fill my pussy with hot cum,” I called out as Jerry slammed his hard cock into me.

Jerry’s body went stiff and his thick cock jerked inside me as I felt the first jet of hot cream flood my hole. Jet after jet of hot cum scorched my bowels. My body shook with bursts of pleasure and I exploded, spraying hot cum on my face. My body twitched and jerked with the most intense orgasm I had ever experienced.

Jerry slowly withdrew from my slick hole and collapsed beside me on the bed gasping for breath. He pulled me against his powerful chest and kissed my neck.

“You’re the hottest woman I’ve ever been with,” he breathed.

I was Jerry’s girl now, at least for the rest of the week.