I’d been looking forward to the long holiday weekend for a while. Christa, my girlfriend, was going away on a girl’s trip, allowing me three days of uninterrupted alone time. Don’t get me wrong, I loved Christa and enjoyed our time together but, there were certain things that I could not share with her.

Arriving home from work on Friday, I ran a hot bath, using plenty of Christa’s sweet smelling bath salts, and poured myself a glass of champagne. Settling in to the fragrant steaming water and sipping the cold bubbly liquid was the perfect way to start my weekend of planned fun. I took my time, shaving myself smooth, between sips of cold champagne. When I first started dating Christa, I’d told her that I kept my body hairless because I’d been a competitive swimmer in high school. She never questioned why I continued, even though I never went swimming anymore. She never questioned why my skin was as soft as hers either, or why she went through so much moisturizer.

After my bath, I slipped on my favorite purple and black lace trimmed bra and panties, and black stockings before pouring a second glass of bubbly and settling in front of the mirror to do my hair and makeup. When I was done, a dark haired vixen with smokey eyes and plump red lips stared back at me in the mirror. Anticipation of the fun to come had me practically trembling with lusty excitement. I finished my transformation off with a simple purple silk baby doll nightie and four inch black heels with gold trim.

Transformation complete, I spent some time posing before the mirror and snapping some new photos for my Growlr profile. Scrolling through the photos afterward, I was quite pleased with what I was seeing, I had come a long way since my first feeble attempts at feminizing myself. Other than the bulge in my panties, I thought I looked quite passable.

Feeling pretty, and slutty, I logged on and uploaded the new photos to my profile. I browsed for hook up possibilities for while with no luck. I was about to logoff, when Jay, an older man I’d chatted with before, and desperately wanted to play with, messaged complimenting my new pics. Unfortunately, he couldn’t meet that night but, did want to have a little webcam fun.

I quickly gathered my toys, lube,and laptop in the living room where I could stream the show on the flatscreen. I’d seen faceless photo of Jay, and his nice thick cock, on his profile but, when his webcam loaded, I got my first look at his handsome bearded face. My dick twitched in my panties at the sight of him. I wanted to play with him even more than I had before.

We chatted a bit as I pranced before the camera, posing for him and showing off my smooth feminine body. I felt so slutty displaying myself for him like that. I just wished he was there to take full advantage of my slutty desires. The thought of his big rough hands roaming my smooth flesh was making my panties wet. For his part, Jay talked dirty to me while stroking his thick hard cock and telling me what he wanted to do to me. His deep, gravelly voice was so sexy he could make me do anything he wanted.

Jay directed me to get on all fours, facing away from the camera, and finger my slutty pussy for him. Which, I was more than happy to do. I moaned and wiggled my ass for him as my finger slipped in and out of my tight needy hole. With my other hand, I grabbed my dildo and began sucking it imagining it was Jay’s thick tool filling my sissy mouth.

“That’s a good girl, you’re a good little cock sucker. Now let’s see you ride that big dick,” Jay directed.

I was so horny at that point, I couldn’t wait to get all eight inches into me and jumped up to stick the dildo on the coffee table with the suction cup. I dropped my panties and, straddling the table, lowered my hungry cunt onto the thick rubber shaft. I stroked my own hard shaft as I rose and fell on the dildo and began moaning like a whore as Jay stroked his hard cock on the TV screen.

“What the fuck!” Christa’s voice exclaimed from behind me.

I whipped my head around to find Christa staring at me with a horrified expression on her face.

“Christa! What’re…?” my voice trailed off as I had no idea what to say.

“Fucking disgusting pervert! What the fuck?” she screamed and ran out, slamming the door behind her.

I stared after her, the dildo still buried in my ass, the only thought in my mind was oh shit! I’ve been caught!

“Wow, that sucks, babe, sorry. Guess I should let you go deal with…that,” Jay’s voice broke in.

When I turned back to the screen, he was holding his still-hard cock and looking pitifully at me sitting there on the dildo with a wilted cock.

I said goodbye to Jay and cleaned up, then tried to call Christa. She didn’t answer, so I texted an apology and asked her to at least call me back. I was in agony waiting for her to call, wondering, and dreading, what she might do, and who she might tell. What would happen if, and when, she told our friends and family? I could never face my parents or brother, not that they would have anything to do with me once they found out. I was sure I would be out of a job if word got back to my boss or coworkers, no way would they allow a pervert like me to stay on. A few of them would might even beat the shit out of me. I was fairly sure that my life as I knew it was about to come to an end.

I finally heard back from Christa Monday morning, when she texted that she was coming to get her things and wanted me out of the house because she didn’t want to see me.

I tried apologizing again and begging her to just call me but, she only responded with insults. Somewhere among the insulting texts, I went from remorseful and worried to angry and unapologetic. I lost my patience with her and told her she was a closed-minded, judgmental bitch for not at least having a conversation with me and, it was my fucking house and she had no right to tell me not to be there. If she wanted her shit, she would just have to come get it when I was home because I’d already changed the locks and she couldn’t get in. That was a lie but, she didn’t know that.

She messaged back that her brother was coming to get her stuff and asked me to have it ready for him. I couldn’t believe she wouldn’t at least talk to me about what happened. I was no longer upset about losing her but, glad she was gone. I packed her things, being careful to get everything to ensure I never had to speak with her again. I was still worried what she might say, and to who, especially after telling her off but, I felt better about standing up for myself in the face of her degrading insults.

A few hours later, Nathan, Christa’s younger brother, showed up to get her things. I was glad he didn’t say much as we loaded her stuff in his car. I didn’t know Nathan well and had no desire to discuss the disastrous end to my relationship with his sister with him. As he picked up the last box, Nathan hesitated.

“Dan, Christa told me about ah… what happened…”

His words were like a closed fist to the face and confirmed my fear that Christa was telling my dirty secret. If she’d told Nathan, it was likely she’d told her whole family all but, guaranteeing I would soon be big news amongst their church congregation.

“Look Nathan, this isn’t anything I want to discuss,” I cut him off and moved to usher him out the door.

“It’s just… I wanted to… I don’t have anyone else to…to talk to,” he stammered.

“What? Talk to about what?” I asked, caught off guard and confused.

Nathan dropped his head and almost whispered, “I think I might be one too.”

“One what?” I asked, even more confused.

“I think I might be a gay too,” he said, his voice shaking and barely audible, “I was just hoping maybe I could talk to you.”

For a moment, I thought he was going to start crying. This had obviously been very hard confession for him to make and I felt for him. I remembered well, struggling with my own sexuality when I was his age. To be honest, I couldn’t say that my struggles were over with at that point either. And, knowing about his religious upbringing, I could only imagine how much more difficult things were for him. I took the box from him and closed the door.

“Come on, let’s talk,” I said, leading him to the living room.

I told Nathan to have a seat on the couch and got a couple beers from the kitchen. I gave one to Nathan and sat beside him. I didn’t know Nathan well, I’d only met him a couple of times when accompanying Christa to family dinners at their parent’s house.

“So, tell me what’s on your mind,” I said, opening my beer and taking a drink.

Nathan stared at the bottle in his hand. “I’ve never had beer before,” he said.

“You want something else?”

“No, I want to try it.”

“What else do you want to try?” I asked, hoping to get the real topic of our discussion started.

“Well, I think maybe, I want ah…maybe I like guys, not ah…girls,” he stumbled, never taking his eyes off the bottle in his hands. He was gripping it so tight, his fingertips were turning white.

“You have a girlfriend don’t you?”

“Yeah, we’ve been going out since high school. I think she wants to get married,” he said, matter-of-factly.

“So, is sex good with her?”

“Well, we haven’t really had sex yet. We make out a lot and she gave me a blow job once. She wants to do more but…” he trailed off.

“But, you don’t want to?”

“I mean, I want to, it’s just, I don’t get excited with her. I don’t know if I can,” his voice grew consistently quieter as he spoke.

“So, when she gave you a blow job, you didn’t get excited?” I asked, unable to imagine not getting rock hard with my cock in someone’s mouth.

“No, I did, it felt good but, I was ah…thinking about um… somebody else doing it,” he answered, actually looking up from the beer bottle for once.

“So, while she was sucking you, you were thinking about a guy?” I asked, my interest piqued.

“Yes, a guy I saw in a porn video,” he looked away, his cheeks glowing bright red.

“Have you done anything with another guy, or are there any guys you want to do things with?”

“No, I haven’t done anything. I’ve thought about doing stuff with a couple guys but, I think they like girls,” he said, finally opening his beer.

“Well, Nathan, you’re at least extremely curious and, I think, probably gay. I know how religious your family is and how hard that must be for you but, you need to know, it’s okay to have these feelings whether they like it or not. I do understand what you’re going through and it’s not easy. I went through the same thing before I had sex with a man for the first time. After I did it the first time, I knew I wanted to keep doing it and a lot of the doubts and fears went away. I don’t know what else I can tell you. You’re the only one who can decide what you want. You can follow through with your desires and do what you want or, you can try to deny them, marry your girlfriend, and hope they just go away, they won’t but, you can hope. I don’t think you’ll be happy trying to live a life you don’t want, and I don’t think she would be happy being married to a man that didn’t want her either,” I explained, hoping I was giving good advice.

“When you did it this first time, how did you meet him?” he asked, looking straight at me for the first time since we sat down.

“He was a friend, we went to school together. We went camping one weekend and ended up fooling around in our tent,” I smiled at the memory.

“Christa said you were dressed like a girl. Do you do that a lot?” he asked, seeming more relaxed.

Another punch in the face, not only was she telling people but, she was apparently giving details too. A knot was beginning to form in my stomach again. I wasn’t thrilled about sharing my deepest secret but, I felt obligated to help Nathan any way I could.

“Yes, I like to wear women’s clothes and feel like a girl sometimes,” I admitted, it was my turn to blush.

“I do too,” Nathan’s face suddenly lit up at knowing he wasn’t alone. “Did you get them from Christa too?”

“No, I have my own, hers wouldn’t fit me,” I smiled, remembering the first panties I had swiped from my own sister.

“Really, how did you get them? Did you just go to the store and buy them? Can I see what you have?” Nathan excitedly rattled off his questions.

His eagerness made me laugh and I took him to see my stash of pretty things hidden in the closet of the spare bedroom. I threw two suitcases containing Dani’s wardrobe on the bed and opened them.

Nathan was like a kid in candy store, picking up all of my pretty things and holding them against himself, imagining how they would look on him. He actually gasped when he found my blue satin and black leather corset.

“It’s so sexy,” he said almost in awe as he held it against his torso, “can I try it on?”

“You can but, I think it’s a little big for you,” I chuckled.

Nathan wasted no time ripping his shirt off and wrapping my corset around his thin frame. I had to admit, with his thin nearly hairless body and delicate facial features, he would make an adorable little sissy.

“Here, let me help you with that,” I said, stepping behind him and tightening the laces as much as possible.

The garment was still way too loose to fit Nathan’s petite frame. Nevertheless, he was ecstatic, posing and admiring himself in the mirror.

“This is amazing, where do you get all of this?” he asked, turning his attention back to the cases on the bed.

“Mostly online, there’s one local shop that has some stuff too,” I smiled, sticking my B cup breast forms into the half cups of the corset.

The corset was too big on Nathan to hold them in place properly. Still, he was ecstatic and began squeezing his new breasts together while staring at himself in the mirror.

“With all of this, I’ll bet you look amazing when you get dressed up,” he said, still staring into the mirror.

“Yes, I look pretty good now, it took a lot of practice to look like this,” I said, taking out my phone and showing him a photo from the night his sister caught me.

“Oh wow, you look so pretty,” he said scrolling through my photos, “could you help me look like this?”

“I think I could make you look even prettier, hun,” I smiled and squeezed his shoulder, “if we get some clothes in your size,” I added, chuckling.

“Let’s get some, you said there was a local shop. Let’s go now,” Nathan was nearly jumping out of his skin with excitement.

“Slow down, Nathan, are you even sure this is what you want? This stuff is expensive, you should be sure before you spend a bunch of money. Maybe you should take some time to think about things,” I cautioned, though, he seemed quite sure to me.

“No, I’m sure. I want to dress up pretty and have sex like a girl,” he insisted.

“Okay, we can go there and find some things to fit you but, not right now. You need to take Christa’s stuff to her first so she doesn’t worry and come looking for you. If you’re still sure you want to do this, come back and we’ll go. Deal?” I said, wondering whether I should get myself involved in what could be a very volatile situation.

“Deal,” Nathan shouted, struggling to remove the corset as quickly as possible.

I helped him get the corset off and he ran toward the door, pulling his shirt on as he went.

“I’ll be back,” he shouted opening the front door.

“Wait, don’t forget the last box,” I called, grabbing the box and rushing after him.

Nathan ran back, grabbed the box, and ran out again. I stood in the doorway, watching him drive away and wondered if I had just made a bad situation even worse. If Christa found out I was teaching her little brother to become a crossdressing sissy like me, I shuddered to think what that might lead to. Still, Nathan was clearly having a hard time and needed someone who understood what he was going through to be there for him. I couldn’t just turn him away, even if it did end up causing more problems for me.

I debated with myself over how best to help Nathan while waiting to see if he would indeed return. I understood the feelings he was having and the trouble he was having accepting who he was but, wasn’t sure I was actually qualified to give advice on how he should handle it, considering what had just happened in my life.

I thought of my own early experiences, sneaking panties and hose from my sister’s drawers, feeling sexy and posing in the mirror, how good it felt to stop fighting the deep seeded urges in me and take a cock in my mouth for the first time, and the fear of being found out afterward. My cock twitched at the memory of sucking my friend’s hard cock in our tent and him exploding in my mouth.

I also remembered how he had refused to talk to me for months afterward and threatened to tell everyone I was gay if I came near him again. I remembered it all, the pleasure and the pain, it would have been nice to have someone to help guide me through those early years. Hell, it would be nice to have somebody who understood to talk to about what just happened with Christa.

Unsurprisingly, Nathan did return, just as excited to start his journey as he had been when he left. There was no doubt in my mind, this is definitely what he wanted. We jumped in my truck and I took him to a little boutique downtown with a discrete backroom dedicated especially to crossdressers. They didn’t have a large selection but, everything they had was high quality and very sexy and the staff were very friendly and helpful.

Elaine, the gray-haired proprietor, was helping a customer when we walked in and smiled pleasantly over the woman’s shoulder as we slipped quietly through the door to the backroom.

“Hi Dani, looks like you’ve brought a new friend,” Linda, one of Elaine’s assistants greeted us as we entered.

“Hi Linda, hi Jenna,” I said, greeting both Linda and the customer she was helping who I had met on previous visits to the store. “This is…” I paused turning to Nathan, “Have you picked a girl name yet?”

Nathan gave me a confused look, “Girl name?”

“A name for the girl you become when you’re dressed. It’s okay, we’ll get to that later,” I explained.

Linda came over to help us and I briefly explained the situation to her.

“Oh, that’s great, I remember buying my first clothes. It was so exciting getting clothes of my own instead of borrowing them.”

Nathan stepped back to look Linda over from top to bottom. “You mean you’re a…a…”

Linda cut him off, “I’m a girl now hun, and you can be too.”

“Wow! You’re beautiful,” Nathan blurted.

Linda smiled and took him by the hand, “Let’s find something pretty for you, sweetie.”

I chatted with Jenna as Linda tried to help an overexcited Nathan find the first lingerie of his very own. Nathan rifled through the racks and displays, ohhing and awwwwing over everything he picked up.

“He’s going to be a very pretty girl,” Jenna said, “ Where did you find him?”

“My ex-girlfriend’s brother,” I shrugged.

“Sounds complicated,” Jenna said, scratching her stubbled chin. “Who’s better, brother or sister?”

“I’m just trying to help him out a little, he’s really struggling with his sexuality,” I explained.

“I’d love to help her out, she’s going to be darling,” Jenna laughed.

“I’m sure you would, horny bitch,” I laughed back.

“Look who’s talking,” she snorted.

Just then Nathan ran up with an armload of clothes, “Look, they’re all so pretty.”

Jenna and I looked through the items one at a time, holding them up to judge how Nathan would look in them. It was hard to judge because they would all look amazing on his petite frame. Linda stood by offering advice on proper sizes and showing us a few sets she thought would be perfect for Nathan. One was the same purple and black set I had been wearing the night Christa walked in on me.

“Oh I have that same set, it’s my favorite,” I commented when Linda held it up.

Nathan grabbed it from her hands and held it against his chest, “We could be twins!” he exclaimed.

“Oh that would be hot,” Jenna leered at the two of us.

“Um maybe this one,” I quickly suggested, holding out a baby blue satin and white lace teddy.

“Maybe both,” Nathan grabbed the teddy from my hand.

We all laughed at his excitement and carried on looking through all of his selections. It took a while as he’d nearly picked one of everything in the store. In the end, Nathan decided on the purple and black bra and panty set that matched mine, the teddy, and a simple red thong and matching bra. I added the prices in my head and asked how much he wanted to spend. He answered that he’d brought plenty of money and didn’t care what it cost. We helped him gather stockings, a black garter belt, as well as a short blue satin robe to complete his outfits. Then Nathan saw the shoes. Initially, he wanted a pair of six-inch stiletto heels but we persuaded him to go for a much lower-heeled sandal to start with.

As we hauled his purchases out to the truck, Nathan spied the display of breast forms. It took another twenty minutes to convince him, he didn’t need those just yet. As we headed back to my house, Nathan couldn’t quit talking about everything he’d seen in the boutique and I knew he would be returning there soon.

Nathan practically sprinted to the spare bedroom with his purchases. His new clothes were already laid out on the bed and he was half naked by the time I caught up. He let his pants and underwear fall to the floor just as I stepped into the room. Nathan may have been small in stature but, the cock hanging between his skinny legs was one of the biggest I’ve ever seen, and I’ve seen a few. He grabbed his new purple and black panties and pulled them on. They fit him perfectly, except for his big cock sticking out the side and dangling down his thigh.

“Get yours so we can be twins,” he said, snatching up his matching bra.

“In a minute, first let’s get you sorted out,” I smiled, as he struggled to get the bra hooked.

Stepping behind Nathan, I hooked his bra, straightened and adjusted the straps, and stuffed my small silicone falsies in the cups.

“There, that’s better,” I said, stepping around in front to make sure they were straight. “Now we need to tuck that away,” I said, looking down at his hard cock sticking out of his panties.

Nathan looked down and tried stuffing his dick back in his panties, without success. I described to him the process of properly tucking his manhood between his legs but, he didn’t really understand what I was telling him. So, I decided to show him by stripping off my clothes and putting on my matching purple and black panties.

“You’re all smooth!” Nathan gasped, staring at my smooth-shaved genitals.

“Ah yeah, I shave everything,” I smiled, feeling a stirring in my groin as he stared at my cock.

“I want to do that,” Nathan breathed, slowly reaching out to run his fingers over my smooth flesh.

My cock jumped at his touch and I wanted him to explore my whole body. I resisted the urge to ravish his young body and stepped back. “I can help you with that,” I offered, envisioning how sexy he would look once we removed what little hair there was from his body.

Gathering my toiletry bag from the closet, I led Nathan to the master bath and ran a hot bubble bath for him. I helped Nathan remove his bra and panties as the tub filled.

We climbed into the tub together and sat facing each other. I lathered up my chest and removed what little stubble there was, then, propped my leg on the side of the tub and demonstrated how to shave it smooth without nicking or cutting myself. I gave Nathan a razor and watched as he did the same, luckily for him, he was naturally almost hairless and accomplished the task quite easily. Next, I sat on the edge of the tub, with my legs spread wide, and demonstrated stretching my scrotum taut and carefully shaving it smooth before doing the rest of my pubic area. With Nathan watching intently as I demonstrated my hair removal routine, my cock had become rock hard and begun throbbing.

I slipped back into the warm water and Nathan took my place on the edge of the tub. His hands were trembling as he tugged and pulled at his scrotum. He hesitantly touched the razor to the taught skin and I reached out to steady his hand and guide the sharp blade across his flesh. Nathan did a fairly good job of shaving himself for the first time and I took over to clean up the few spots he had missed. As I manipulated his testicles, his hard cock bobbed just inches from my face and leaked a constant stream of pre cum.

I couldn’t help myself, I had to taste it. I leaned forward and kissed the wide fleshy tip before swirling my tongue around to gather the tangy cream collected there. Nathan let out a long groan as my lips engulfed his thick oozing tip and slid down his shaft. He was so big, it took a few tries to take all of him but, I did manage to get my lips around the base. I loved the way he moaned and caressed my head as I sucked him. My preference has always been hairy masculine men but, Nathan was just so cute and eager I loved slurping his big young cock. His moans turned to gasps and his hips began to shake just before he filled my mouth to overflowing with steaming cream.

“Oh wow, that was amazing!” he gasped, holding my shoulder for support.

“Mmmmm it was,” I grinned, savoring his taste on my tongue.

Nathan slid off the tub’s edge and reached for my throbbing cock, “Can I suck yours,” he asked with a pleading look on his cute young face.

“Let’s go get you dressed first,” I said, cupping his cheek and dying to see him in his new lingerie.

We quickly dried off and I held Nathan’s panties for him to step into then, slid them up to his thighs. With his panties in place, I lifted Nathan’s dick with one hand and carefully pushed his freshly drained testicles up into his body, then tucked his cock back between his legs. Freshly shaved and tucked, he was the picture of feminine beauty. I couldn’t help smiling as I pulled his panties up to hold his big clit in place.

Nathan stared at himself in the mirror as I fastened and adjusted his bra for him. He looked down, running his hand over the smooth front of his pretty panties, and smiled the biggest smile ever.

“I look like a girl,” he said, his voice filled with awe.

“You do, you are a beautiful girl, hun,” I smiled at him in the mirror and let my hands slide down to his hips and around to cup his firm little ass.

Nathan turned in my arms and rose up on tiptoes to kiss me, “Thank you for helping me.”

My hard throbbing cock was mashed between us as I returned the kiss and pulled his smooth young body against me. Our lips and tongues twisted together as I steered us into my bedroom and onto the bed. Nathan began grinding against my swollen cock as I rolled him on top of me and gripped his firm round ass. I pulled him against me, increasing the pressure on my cock as he squirmed against it. Nathan’s fingers found my nipple and began pinching and twisting it. I groaned into his mouth and pushed his hips away, fearing I was about to cum.

“Wait, wait, I don’t want to cum yet,” I breathed after seeing the confused look on his young face.

Nathan just grinned and resumed kissing me as his hand slid down my torso. His fingers wrapped around my hard shaft and slowly slid from base to tip and back as he kissed a trail down my body. He smiled up from between my spread legs and flicked his tongue over the throbbing purple head of my swollen member.

“Oh careful, I might not last long,” I warned, struggling to ward off orgasm.

Nathan’s soft warm lips descended over my precum-coated tip and began sucking me. I squeezed my eyes shut and tried to think about anything but, how good his warm lips and tongue felt on my throbbing cock. I wanted this to last and Nathan was not making it easy as he bobbed his mouth up and down my throbbing length. In his enthusiasm, Nathan took too much of me in and immediately pulled back, gagging and choking.

“Slow down, don’t try to take too much,” I cautioned, grateful for the brief respite to pull back from the edge.

“But I want to do it for you, like you did for me. It felt so amazing,” he said, wiping his mouth.

“I’ve had a lot of practice, this is your first time and you’re doing just fine, it feels incredible. Just take as much as you can and stop when it feels like you’re going to gag, then pull back and try to take a little more the next time,” I coached as his lips engulfed my swollen tip once again.

I don’t know what Nathan was doing with his tongue but, it felt amazing and I was soon racing toward orgasm again. He did as I had instructed, sliding his warm mouth slowly up and down my throbbing cock, taking just a little more of me each time. I moaned loudly as I ran my fingers through his hair. The way he was sucking my cock, I was certain he’d spent a lot of time thinking about what he’d do if he ever got a hard cock in his mouth. My belly began tightening and I thought I’d better warn him I was about to explode.

“Mmm that’s so good Nathan, I’m going to cum,” I grunted as my hips started to shake.

Nathan looked up with his lips still wrapped around my shaft and began bobbing his head faster. I threw my head back and arched my back as the first hot jets of cum shot through my throbbing member. I groaned and grunted as my hips jerked and my balls emptied into Nathan’s hungry mouth. Nathan did his best to swallow my load but, gagged and pulled back and the last bursts coated his face. He swallowed what was in his mouth before sucking my wilting cock clean. When he was done, Nathan looked up with a wide smile on his cute cum coated face.

“That was amazing, Nathan. Now come here and let me help clean you up,” I smiled back, reaching out to wrap my arms around him as he crawled up my body.

My hands found his firm ass as I licked my cum from his cheek and pressed my lips to Nathan’s so we could share. Nathan’s eager tongue explored my cum filled mouth and he ground his hard no longer tucked cock against my own spent member. I gripped his firm round ass, pulling him harder against me increasing the pressure on his hard cock. Our tongues danced together as I slipped my finger between his cheeks and touched his virgin pucker for the first time. Nathan flinched at the touch and moaned into my mouth before grinding his hips even harder against me. I teased circles around his puckered little hole and squirmed my hips against his.

Even though I had just cum, I could feel my dick growing hard against Nathan’s hard throbbing shaft. Our breathing grew labored as our mouths twisted together and our bodies grew hot. I pressed harder as my finger teased Nathan’s tight hole and I could feel him opening up. With a little more teasing and pressure, my finger slipped into his tight hole. Nathan moaned and bucked his hips and hot semen burst from his throbbing young cock. The sensation of Nathan’s hot cum covering my cock and his continued grinding soon triggered my own orgasm and I added my cum to the sticky mess flooding our cocks.

Nathan collapsed on top of me, nuzzling his lips against my neck, “That was so amazing,” he gasped between kisses.

“Yes, you are,” I breathed, holding him against me.

We lay quietly together enjoying the warmth of our flesh pressed together, sharing occasional kisses and caresses. It was nearly midnight when we finally rolled off the bed and cleaned ourselves up. We decided it would be best to keep Nathan’s new wardrobe at my house, as he couldn’t risk it being discovered at home. We made room for Nathan’s things in the spare bedroom with mine. Nathan made me promise we would get together again very soon before, reluctantly kissing me goodbye. That was a promise that was not hard to make as I wanted more of his delectable young body. I fell into bed feeling both satiated and hungry for more.

I was tired but, couldn’t sleep. My mind was occupied with worries about Nathan regretting what we’d done. I knew it was what he wanted, maybe even needed, and he’d definitely enjoyed every minute but, considering his religious upbringing, he was bound to experience some doubts and regret about following through on his taboo yearnings. In addition to that, I couldn’t help worrying that I’d taken advantage of him while he was vulnerable. I just couldn’t help myself, he had looked so cute and that big cock staring me in the face. I had to taste it. If all that wasn’t enough, worries about what might happen if his family, especially Christa, found out what we’d done, crept into the mix. I did finally manage to get some sleep and dreamt about a proud little sissy prancing in her new lingerie.

I had promised Nathan we would get together again very soon, but I wasn’t expecting to find him waiting in my driveway when I arrived home from work the next day.

“Sorry, I’ve been thinking about wearing my teddy and stockings since I left last night. I had to come over,” Nathan greeted me with an excited grin as I climbed out of my truck.

I chuckled at his excitement. “No problem, hun, come on in. We should probably talk about last night anyway.”

“It was the best night ever! I’m so glad I decided to talk to you,” Nathan exclaimed, running to the gurl room.

“Do you think I need to shave again?” Nathan called from the gurl room as I leafed through my mail.

“I doubt it, but it would probably be good to get some practice if you want,” I answered, turning around to find Nathan standing in my kitchen naked, and already hard. I instinctively licked my lips while staring at his tantalizing tool. I couldn’t help but, laugh as I stared at his over-excited organ.

“So, you’re okay with everything that happened last night? No regrets or anything?” I had to ask.

“Oh no, I’ve wanted to do it for so long, it was the best time ever. I felt so good when I left here. Mom even asked what I was so happy about this morning. Of course, I couldn’t tell her and I started getting hard thinking about it. So I had to wait until she left the room to get up from the breakfast table,” he giggled.

“Okay, I just wanted to make sure you’re okay with everything,” I smiled.

“I’m more than okay. You make me so horny,” he said, crossing the room to pull me in for a kiss.

The feel of his warm smooth flesh caused an instant reaction in my pants as our lips met for a long slow kiss. Memories of my own initial forays into dressing and exploring sex with men flooded my mind as my hands roamed over Nathan’s young body. His excitement was perfectly understandable to me.

“Dan, will you fuck me tonight? I want to know what it feels like,” Nathan said, pulling his soft lips away from mine.

“Are you sure you’re ready for that? You should take your time and not rush things,” I cautioned, at the same time wanting to bend him over and slide my cock deep in his cute little virgin ass.

“I’m sure, I’ve been thinking about this for a long time and I’m ready to find out what it’s like,” Nathan insisted.

“Okay, but we’ll need to get you prepared first,” I agreed with a raging hard-on threatening to tear through my jeans.

“Really? Okay just tell me what to do,” Nathan beamed like a kid on Christmas.

I sent Nathan to run himself a hot bath while I retrieved my enema bag and some lube from their hiding place in the spare room. I joined Nathan in the bathroom and explained how to fill and use the enema bag. For the first time, I saw fear and indecision on his face as I explained the process of cleaning himself out.

“You don’t have to do this, if you’re not ready,” I assured him.

“No, no, I’m ready,” he insisted, not quite as enthusiastically as before.

I left Nathan to his preparations and went to shower myself. Unlike Nathan, I did need to shave again as I was already quite stubbly. It was difficult not to grab my cock and start stroking as the thought of taking Nathan’s virgin ass had me practically trembling with excitement. I could only imagine how Nathan was feeling at that moment. My first time had been spontaneous, there had been no planning or preparation and it hadn’t been the greatest experience. It wasn’t horrible, but it could have been so much better if either of us had known what we were doing. I was happy that Nathan would benefit from my experience. I wanted this to be a memorable event for him.

On my way to the spare room, I popped in to see how Nathan was coming with his preparations. He had finished cleaning himself out and was shaving his legs.

“Doing okay in here, hun?” I smiled at the concentration on his face.

“Yeah, clean as a whistle, inside and out,” he answered, blushing.

“That’s good, I’m going to get dressed while you finish up in here, take your time,” I said with a horny smile.

Nathan’s special night called for a special outfit. Searching through my wardrobe, I decided there could really only be one choice, my blue satin trimmed leather corset and matching satin panties and, of course, black high-heeled boots and stockings. I was just pulling my boots on when Nathan walked in, preceded by his magnificently hard cock.

“Wow, you look amazing,” he blurted upon seeing me.

“Well, thank you hun, but I’m sure you’ll look even more amazing when we get you dressed,” I smiled back.

“I hope so. What should I wear?” he asked, picking up his pink and white teddy.

“That will be very pretty on you but first, there’s one more thing we need to do,” I said, taking a small butt plug from my toy box.

“What’s that?” he asked, reaching for the plug.

“It’s a butt plug, it’s to help loosen you up first,” I smiled, popping the cap on the lube.

I walked behind Nathan, gently caressing his firm ass and kissing his neck. Nathan moaned quietly and pushed back against me. My cock threatened to tear through my panties as I pushed him to lean over the bed. Placing his hands on the bed, Nathan pushed his ass out, displaying his puckered pink hole for me.

“Just relax, baby, you’re going to enjoy this,” I said, squirting some lube on my finger and gently rubbing around his waiting hole.

Nathan shivered at my touch and bent lower. He began arching his back and wiggling his ass as my finger made circles over his slick hole. When I could feel his virgin hole beginning to open up, I added more lube to his pucker and the butt plug.

“You ready, baby?” I asked, pressing the small tip of the plug to his glistening entrance.

“Yes,” Nathan breathed.

I slowly slid the plug halfway into his puckered hole then retreated and slid it back in, repeating the process over and over until the toy was seated firmly in his rectum.

“How does that feel, hun?” I asked, wiggling the plug inside him.

“Mmmmm it feels weird but good. I like when you wiggle it like that,” he answered, clenching his ass on the toy.

“Good, now put some clothes on and we’ll do your makeup, you little tart,” I teased, giving the plug another good wiggle.

“Makeup, really?” Nathan shouted, spinning around and snatching up his teddy.

“Yes, really, I’ll be in the bathroom, when you’re ready,” I said, taking my makeup kit and suppressing a laugh at his excitement.

While my makeup skills still left something to be desired, I had perfected my smokey eye technique and was just finishing up when Nathan joined me. As expected, he looked wonderful in his teddy, stockings, and heels. With his flawless complexion, I didn’t think we needed to bother with the foundation and blending that my face required so I went straight to showing him how to properly enhance his eyes.

“So have you decided what your girl name is going to be?” I inquired as we worked.

“I was thinking maybe, Natalia or Nancy. What do you think?” he asked while trying to apply eyeliner without stabbing himself in the eye.

“I like Natalia, but you need to choose a name that suits the girl you want to be,” I answered, surprised at how quickly he was picking up the makeup techniques I was showing him. It had taken me months to learn what he was doing in just minutes.

“Natalia. I want to be Natalia,” he announced, reaching for the blush.

By the time Natalia finished applying her pink lipstick and I brushed out her hair, there was no trace of Nathan to be seen, just a beautiful young sex pot ready to be ravaged.

“Damn, I knew you’d be a gorgeous girl, but you’re absolutely stunning,” I exclaimed, looking Natalia over from head to toe.

Natalia twirled in front of the full-length mirror on the door, staring in awe at herself. “I’m so pretty,” she exclaimed, holding her hands to her pretty face. “Oh my God, Thank you so much for this,” she said, throwing her arms around me.

“It was my pleasure baby,” I said, holding her against my silicone-enhanced chest. She looked up with tears in her eyes and rose up to kiss me. “Don’t cry hun, we’ll have to redo your makeup,” I smiled, dabbing her eyes with a tissue. “Now there’s one more thing we need to do,” I added with a lust-filled grin.

“What’s that?” Natalia asked, her big brown eyes staring up at me.

“Turn around and lean over the vanity,” I smiled, showing her the bigger butt plug I’d been hiding from her.

A horny smile formed on Natalia’s cute face and she turned to stick her firm little bottom out for me. I took a moment to admire and caress her firm smooth cheeks before pulling her teddy aside and popping the plug already filling her ass in and out a few times. Natalia whimpered and pushed her ass out further as I teased her virgin hole. Tossing the smaller plug in the sink, I kissed her neck and pushed more lube into her tight little hole, before pressing the larger plug gently into her tight opening. With a little moan, Natalia wiggled her hips and I pushed the toy further in. I continued kissing and nibbling at her neck as I seated the larger toy firmly inside her and wiggled the base until she began to squirm.

Natalia was so eager and responsive to everything, my cock was severely testing my pantie’s ability to contain it. I had known Nathan would be a beautiful girl, but seeing him completely transformed into Natalia was nothing short of breathtaking. There was not a trace of Nathan anywhere to be seen, just Natalia and she was gorgeous.

“I can’t believe how sexy I look. Here, get some pictures for me,” she said, grabbing her phone.

I took Natalia’s phone and she immediately began posing. “I’m not sure we should do this. If anyone gets ahold of your phone they could send the pictures to anyone or post them online,” I warned.

“No, I’ll download them on an encrypted thumb drive, no one will be able to get into it,” Natalia grinned. “What do you with yours?”

“I’m just careful not to let anyone have my phone,” I shrugged, realizing I wasn’t nearly as tech-savvy as Natalia.

“You should do the same thing with yours. I can show you how,” she offered.

“That’s probably a good idea, thanks hun. Now, stand beside the bed and give me a sexy pose.”

I got some really good shots of Natalia doing some really sexy poses, including some x rated ones exposing the jeweled plug in her virgin ass and delicious cock. She was just the sexiest thing ever.

When we were done, I led Natalia to the living room, where I poured us each a glass of wine and snuggled beside her on the sofa while we scrolled through her photos.

“I can’t believe that’s me, you made me look so sexy. I love it,” she exclaimed, seeing the sexy photos of herself.

“I didn’t do anything, hun, that’s all you,” I smiled.

“Let’s look at your pics now,” she suggested with a horny grin.

With a shrug, I opened my laptop and logged into my account so Natalia could see the photos of me.

“Oh wow, you look so hot, and naughty in these. Look at all the messages you got. Do you meet a lot of guys on here?” Natalia said with a naughty smile.

“Ah no, I get a lot of messages and chat with guys but, I’ve only met a couple of them,” I replied with reddening cheeks.

Natalia opened my mailbox before I could stop her. Of course, the first message to pop up was from Jay about the night I got caught and included a nice photo of his hard cock.

“So, you were camming with this guy when Christa walked in?” Natalia asked, apparently, Christa hadn’t given all the details of what had happened.

“Uh yeah, I was doing a little cam show for him,” I confessed, feeling my face grow hot with embarrassment.

“That sounds fun. Well, except the getting caught by Christa part. What were you doing for him?” she asked, her voice growing excited.

“I was…riding a dildo when Christa came in.”

Natalia’s mouth dropped, “I can’t imagine how bad that must have been for you. Sorry but, if she hadn’t caught you, we wouldn’t be here now.”

Natalia leaned in to kiss me and thoughts of the incident faded as we shared soft kisses, between sips of wine. Our hands began to explore one another’s smooth feminine body. Natalia lay on her belly and took my already stiff cock in her warm mouth and began sucking me. Though inexperienced, she gave an amazing blow job. Her warm soft lips slid up and down my stiff rod, as my hand slid across her back and firm round ass. I had to fight to keep from cuming in her mouth as I wanted to save that for her virgin boipussy.

My fingers slipped between her firm ass cheeks to wiggle the plug filling her and she moaned around my cock, nearly causing me to spill in her luscious mouth.

“Oh wait, hun, I don’t want to cum yet,” I breathed, pulling her mouth from my throbbing cock.

“Are you ready to fuck me now?” Natalia asked, rising up to kiss me.

“Mmmm almost baby, just kneel right here,” I answered, guiding her to kneel on the sofa as I moved around behind her.

Unsnapping the crotch of her teddy, I removed the plug and knelt behind her. Holding her round cheeks apart, I leaned in and swiped my tongue across her pink little hole, bringing a surprised gasp from her mouth. As my tongue swirled around Natalia’s eager hole, I began slowly stroking her hard cock, causing her to moan even louder. When she began squirming and pushing back against my probing tongue, I knew she was ready and rose to stand behind her.

Natalia wiggled her cute little bum as I lubed my impossibly hard cock. I wanted to drive hard into her virgin rosebud and fuck her hard and fast but, knew I had to control my more animal instincts and make this an amazing experience for her. She gasped as I touched my slippery mushroom head to her inexperienced hole.

“Okay relax, when you’re ready, push back slow and steady,” I instructed, letting Natalia take control of her first penetration.

I held my throbbing shaft steady as she began pushing back with a quiet moan. I could feel her beginning to stretch around my bulbous tip and it felt amazing. I had to resist the urge to plunge into her as she rocked forward, then back again. She moaned as my mushroom tip slipped past her tight opening.

“Ohhh, it’s big,” she whimpered.

“It’s okay, just take a breath and wait while you get used to it. Pull off if you need to,” I said, rubbing her back.

After a few deep breaths, Natalia cautiously rocked forward and back slightly.

“Ohhhh, mmmm,” she sighed, pushing back a little further each time. “Ohhh that feels better.”

I watched as her hot tight hole slid back and forth taking in more and more of my hard shaft until it was buried entirely in her hot little hole. I held her hips and ground against her firm ass.

“How does that feel baby? You’ve got my cock all the way inside you,” I asked, fighting the urge to cum as my shaft shifted in her velvety hole.

“I do? Mmmm it feels good,” she sighed.

Holding her hips, I began slowly stroking the full length of my cock in and out of her hot boipussy. As I fucked her, my hand slid around to grip her thick swollen clitty and stroke it in time with my thrusts. She gasped and moaned with every thrust into her hot slick hole.

“Ohhh yes, mmmm fuck me, daddy,” she moaned.

I had to pull out and grip my cock hard to keep from filling her with cream too soon. I wasn’t ready for her first time to end just yet.

“Why’d you stop?” she asked looking back over her shoulder, looking disappointed.

“I just need a minute to settle down, I didn’t want to cum yet,” I explained. “Come on, I want you in my bed.”

I removed my panties as Natalia lay back on my bed, spreading her legs wide and fingering her tempting ass. She looked angelic and slutty at the same time. Climbing on top of her, I once again entered her as our tongues embraced passionately. She moaned into my mouth as her hands gripped my ass, pulling me into her. Our tongues danced within the heat of our joined mouths and my throbbing shaft stroked steadily into the slick heat of her pussy. Natalia’s continuous moans pushed my lust to new heights. I rose up, gripping behind her knees and pushing her smooth legs higher and wider, allowing me to drive my cock deeper into her.

“Yes, yes, yes, fuck me. daddy, fuck me,” she cried.

The thought popped in my head, as I thrust harder and faster, that Natalia was a much better fuck than her sister had ever been. The thought was quickly pushed away as I felt the familiar pull of impending orgasm low in my belly. Sweat trickled from my brow as I drove, hard and fast, toward orgasm. I stroked Natalia’s swollen clitty in time with my thrusts.

“Oh oh yes yes oh!” she cried as hot cream sprayed across her crumpled teddy.

“Oh fuck, fuck, I’m…” I grunted, as her tight hole spasmed around my hard shaft and I filled her inexperienced ass to overflowing with my own hot cream. My climax rocked my body and took my breath away, leaving me spent and panting as my cock continued to twitch in Natalia’s creamy hole. I continued slowly stroking my deflating shaft in Natalia’s slick pussy as I leaned down to kiss her panting lips.

“Oh my god, I never knew how good it would feel. Thank you,” Natalia breathed as I rolled off of her.

“You don’t need to thank me, I loved it more than you imagine. You’re one sexy little slut,” I breathed, pulling her in for another kiss.

It was after midnight when Natalia emerged from the bath cloaked in her boring boy attire.

“Thank you so much for everything, the whole night was wonderful. When can we do it again?” Nathan asked, wrapping his arms around my waist and rising up to kiss me.

“It was my pleasure and we’ll do it again soon. You have my number and you can come by anytime you want to let Natalia out to play. But, we should be careful, your parents might start wondering what’s going on if you’re out this late all the time,” I answered, holding him tight.

I slept soundly that night, I knew Nathan was elated with everything that had happened, whatever consequences may come.