And then I came. She was ready for it, pulling her fingers out from my ass and using them to catch my cumshot. It was a strange feeling when she pulled those fingers out of me—like I was suddenly empty, left agape. But that emptiness wouldn’t last long. Once she had my whole cumshot in the palm of her hand, she wiped it up and down the length of her purple dildo, coating it evenly. A few globs dripped off onto our clean bed sheets.
She pressed that cum-covered tip against my butthole. “Ready to be fucked?” she asked. But she didn’t wait for an answer before penetrating me deeply. She pushed that thick dildo inside of my body, along with my own warm cum. It was a weird feeling, having my own jizz deep inside of me. But I kind of liked it. Just the thought of it sloshing around inside of me made me aroused all over again.
Janie sunk in deeper and deeper, stretching me wider and wider. I grabbed the bed sheets tightly and groaned. I felt my own cum oozing out the edges of my tight hole, dribbling down my butt cheeks. “You’re so tight,” Janie said with that big grin still in her voice.
She started to thrust slowly—and that’s when I noticed the humming. It was quiet at first, but as Janie started pumping faster, it became louder. It was coming from her—right from that big strap-on. Was there a built-in vibrator? Was it buzzing harder as she fucked me harder? Once she really got going, I could feel that vibration buzzing down the length of that cock. It felt good—too good. I planted my face on a pillow and I started to moan. She was pumping me with the full length of her artificial cock. I could feel that big tip and those hard plastic veins rubbing my insides. I squirmed and my cock was throbbing all over again. Was I about to come again? Could a man come twice in the span of fifteen minutes?
Janie held my hips firmly. She pumped fast and without hesitation. Her fit pelvis slapped my soft tush over and over and over. Then that tingling in the tip of my cock became overwhelming. I reached down and squeezed my rod just as it burst: a second cumshot, coating our freshly cleaned sheets.
I screamed out and then Janie did the same. She thrust herself into me one last time and then she stumbled back, slipping her rod out, leaving me feeling emptier than ever.
The room was silent for the next minute. I was slow to turn over. Janie was looking at me with a dark red face. She smiled, showing her perfect teeth. Then she said, “Thank you for doing that for me.”
“It was fun,” I said. I watched as her face lit up.
“Really?” she asked.
“Yeah.” I stood up slowly. My legs wobbled slightly, still feeling the effects of the euphoria. I took a deep breath. “We’d better get ready for our night out, huh?” So we got right to work.
CHAPTER VIII
The party was fun. And the guys were right—we didn’t have to spend a dime. Guys kept buying drinks for us, even when we already had full drinks in our hands. I guess there are a few perks to being female. Though perhaps we paid for those drinks with the time we took getting ready: styling our hair, doing our makeup, and so on.
We did shots together, we danced together, and then we ended up at opposite ends of the bar for a bit, while Janie continued to dance and I soaked up some more attention at the bar. I kept standing up on my tippy toes just as she stood up on hers. We would wave at one another and then we would return to the fun.
But the fun came to an abrupt end when I met back up with Janie and she said, “There’s a guy here that wants to sleep with you.”
I laughed, taking it as a compliment at first—then I was shocked with Janie said. “You should do it. It would be super hot.” I thought she was joking for a moment, and then I saw that red face—that same red face she had on when she presented that strap-on dildo.
“Wait—you’re serious?” I said.
“I’ll be there with you. I’ll even hold your hand.” She made a big smile, and then her eyes became wide as she realized I wasn’t into the idea even a little bit. I was deeply disturbed that Janie ever thought it was an okay suggestion to make. Maybe there was still a lot to this girl that I needed to learn. Maybe her overpowering fetish didn’t end with a dress and a strap-on. “You don’t have to do it. I was just—I was just kidding. It was a joke.”
But I knew she was lying now. I knew that she wanted me to do it. I knew that this was just the next level of her fantasy—maybe the final level, or maybe it would just get crazier. I didn’t want to sleep with a stranger—especially not a male stranger—but I also didn’t want to let my wife down. I felt like I was being the perfect husband: dressing up for her and letting her peg me in the ass. It felt nice, giving my beautiful wife everything she wanted. I felt like I really did deserve her love. I felt like I really was proving all of my critics wrong—that Janie really did want to be with a guy like me.
“Which guy?” I asked.
Janie was slow to respond. She looked into my eyes and I watched as that little glow returned for a brief second. Then she turned around with her red cheeks and pointed to a surprisingly fit and handsome man standing at the bar. He had tattoos up and down his thick arms, and his hair was neatly slicked back. “That guy,” she said.
My heart stuttered. Could I do it? Taking the dildo didn’t hurt, so would a cock really be so bad? If Janie was there with me, would it really be so horrible? Just how badly didn’t I want my wife to have everything in the world?
The man turned and looked at me. He smiled, making my heart plummet down into my stomach. I took a sharp breath of air into my lungs and then I looked away quickly.
“What is it?” Janie asked, looking into my eyes.
I bit down on my tongue. I remembered that smile on her face when I told her I wanted to go to the temple, instead of going back to the hotel. I remembered that glimmer and that joy. I loved that joy. I wanted her to have it forever—for the rest of her life. And now I was in a position to give it to her. “Tell him I’ll do it,” I said.
Janie hesitated. “Wait—what? Seriously?” she said.
I nodded my head. “Only if you’ll be there with me,” I said.
And there it was: that glimmer—that joy—that smile and that glow. Janie bit down on her lip and then she said, “He already knows that you’re a ladyboy. He likes that. He promised that he would be gentle.” Then she leaned forward and whispered into my ear. “He thinks you’re a prostitute, so he’s going to pay us pretty good money.”
I nodded my head. My mind was swirling fast and my stomach was bubbling and groaning. I had no idea what I was getting myself into. I was literally whoring myself out. In a matter of days, I had gone from being a quiet young man to being a ladyboy prostitute in Thailand. How was that possible? Was it real? Was I dreaming?
Janie slipped away from me to tell the man the good news. Then, she came back with the guy. “This is Richard,” she said.
Richard held out his hand. “What’s your name, beautiful?” he asked.
Janie looked at me with wide eyes, expecting me to know my own name. I spat out the first name that came to mind. “Leanne,” I said. I shook the man’s hand. He had big hands, rigid with muscle. He squeezed my hand tight, sending a shockwave of terror down my spine.
“Let’s get a cab,” Janie said. And the next thing I knew, I was sitting between Richard and Janie in a tiny yellow cab, headed back towards our hotel room. Richard casually reached down and put a hand on my thigh, making my skin crawl cold. I looked over at Janie. Her smile put me at ease—at least for a couple of minutes. Then I saw the hotel materializing in the distance and that terror came rushing back. This was really happening. I was really about to have sex with a man for money, while dressed as a girl.
CHAPTER IX
Janie rushed me into the bathroom as soon as we were back at the hotel room. We left Richard sitting on the edge of our bed.
Janie put both of her hands on my shoulders and she looked into my eyes. “You really want to do this?” she asked. “Because there’s no pressure. You don’t have to. I know that you’re just trying to make me happy—and I appreciate it. But I
’m not happy if you’re not happy.”
And I felt the same way: I wasn’t happy unless she was happy. And I knew that she would be happy if I went through with it. So I just shook my head and said, “I’m sure.” She stared into my eyes for a moment longer, and then she slipped out of the bedroom to fetch me a sexier outfit.
It was a lace one-piece, similar to the one she wore when she fucked me in the ass with the strap-on. It was tight, but it fit perfectly. It was soft in all the right places. Janie let me know that it was worth about five hundred bucks, but she got it for free from a modeling shoot she did. Once I was dressed, Janie continued to get me ready for my ‘date’. She told me to bend over, so I did. She squirted some lubricant into her hand and then she stuck a finger up my butt. “This should last the next hour or so,” she said. The thought of being fucked for an hour made my heart pound even harder.
When she asked me to walk towards the mirror so she could fix up my makeup, I realized my joints had become stiff. I was stuck in place, rigid with terror. It took all of my willpower to break free from that stiffness. And then, as Janie brushed some powder onto my face, I found myself wondering if it was worth it. Why was I so desperate to make her happy? Did I really love her, or was I just obsessed with proving everyone wrong? Was I with her because I loved her or was I with her because she was way out of my league—the only beautiful woman I would probably ever be able to get?
She leaned forward and kissed me on the lips, reminding me of our wedding day. I suddenly remembered seeing those joyful tears in her eyes when we became married. I remembered how happy that joy made me. I remembered our first dates, walking through the city, hand-in-hand. Sure, she was beautiful, but it wasn’t her beauty that made me fall in love with her. It was that glimmer in her eyes: that warm glow of excitement and joy. It was contagious, and it was what I wanted to be with for the rest of my life. I did love Janie, and I loved seeing her happy.
So I took a deep breath and bit down on my tongue. “I want you there with me the whole time,” I said.
“I’ll be there.”
We went out together. Richard was already naked, with his long cock resting peacefully on our bed. “Here she is,” Janie said, holding out her arms to present me.
I smiled and tried to pose, but my posture was nervous. Richard stood up and walked towards me, suddenly towering over me, making me feel small and weak. He put his hands on my arms. I looked down and saw his long flaccid cock swaying from side to side. He tilted my head up and leaned in for a kiss. I closed my eyes and tried to imagine Janie’s lips. Then I felt Janie’s hands landing on my sides. She was there with me, supporting me, putting my mind at ease. I kissed that tall man back. I even let him slip a bit of tongue into my mouth.
His stubble beard tickled my chin. His rugged hands held me a bit too tight, hurting a little bit—but I didn’t say anything. He didn’t even need to use his strength—the weight of his hands on my shoulders was enough to pull me down to my knees. Janie sunk down to her knees behind me. She had her head hovering over my shoulder as I leaned in to suck that giant cock. She even held my hair back as I inserted the warm, throbbing member into my mouth. “That’s a girl,” she said. “Suck it. Just like that.” She stroked her fingers gently through my hair.
Sucking cock wasn’t so bad. In fact, it was kind of satisfying, the way the cock grew and throbbing in my mouth, letting me know that I was doing a good job. I kind of liked hearing the moans slipping from the man’s lips, knowing that I was responsible for all of them. And he was a handsome guy—he wasn’t just some scrawny creep. He was a gym rat with a chiselled jaw and thick arms—the kind of guy that should have been with a girl like Janie—but he was with me, and I was with Janie, and that thought was profoundly heart-warming for a reason I couldn’t quite put my finger on.
Janie reached down between my legs while I sucked Richard’s cock. She got her fingers under my lingerie and she started to massage my cock until it was hard—then she started to pump it. And even though I’d gotten off half a dozen times in just a couple of days, I still became rock hard in an instant. Maybe it was the way Janie moved her fingers, or maybe it was the thought that I was successfully pleasuring a hulk with my mouth.
The man’s cock was suddenly feeling harder, bloating near the tip, throbbing as if he was about to burst. He pushed my head back and grabbed his cock, squeezing it tightly as if to stop himself from coming. Had I really come that close to getting him off with just my mouth?
“I just need a second,” he said. He closed his eyes and took a deep breath. He didn’t want the fun to end—and I didn’t want it to end either. I could feel Janie’s smile behind me, beaming against the back of my head. I loved that smile. I never wanted that smile to go away.
So I stood up and led the man over to the bed. I made him lay down on his back, and then I started to rub his muscular chest. Janie was behind me again, watching with those glowing eyes, watching as my fingers slid over that thick chest and those rolling abs. He was a bit sweaty and very hot, as if there was a furnace burning inside of him. I wanted to give his throbbing cock a rest, but I also wanted to reach down and stroke it. It was a temptation that I fought hard to fend off.
Though I still reached down and played with his big ball sack for a few minutes, even teasing his asshole with the tip of my finger. I let a little giggle slip, and then Janie let one slip behind me. We were having fun. It was the most fun, unique honeymoon that I could imagine, and I was glad we were experiencing it together.
She helped me up on top of him, getting my tush lined up with his erection, pulling my lingerie gently to the side so that my lubricated asshole was ready for penetration. Richard’s face was dark red. He looked down at my cock, which was also out from my lingerie. He reached out to touch it, but Janie slapped his hand away. “That just for me,” she said with a big cheeky smile. Then Janie held my cock and let out a long elated sigh, as if she’d been waiting years to touch that cock. I loved that she loved my sissy shaft, and I loved that it was for her and her only.
I began to sink down, feeling that thick tip squeezing into my tight hole. I closed my eyes and took a deep breath. It penetrated suddenly, so I stopped. It wasn’t the same as the dildo. This was warm and throbbing and a little bit wet with sweat and pre-cum and spit. It felt real and alive—because it was! I took another breath and then I sunk down another inch. That inch felt like a foot. And the next inch felt like another foot. It wasn’t long before I thought I could feel his cock pushing up into my throat, even though I knew that was impossible. And it wasn’t long before my tush was pressed against his lap. I had all of him inside of me: eight inches of swollen cock, deep in my butt.
“Good job, babe,” Janie said, rubbing my sides gently with her perfect hands.
I started to bounce, massaging the length of that cock with my tight anus. I bounced up and down, faster and faster, clenching my butthole every time I felt his cock bloating up. I kept thinking he was about to burst, but somehow he kept holding back. I looked down into his eyes and he looked away from my eyes quickly, as if he was intimidated. I was overwhelmed with an intense gush of excitement, knowing that I was intimidating one of the most handsome men I’d ever seen. I really did make a better woman than I did a man. And maybe that wasn’t such a bad thing. Maybe being a beautiful woman had its perks. Free drinks, being able to skip lines, men desperate to give me money for sex—and Janie. Janie was one of the perks of being a convincing woman. I knew that she loved me for me—but I also knew that I was making her happy because of a little skill that I didn’t know I had just a few days before.
“Shit!” Richard groaned. I could feel him bloating up inside of me. I clenched his rod hard and I bounced faster. He squirmed and I screamed out as Janie finished jerking me off. My cum shot onto his chest, and then his cum shot into my asshole—deep inside. His load seemed never-ending—blast after blast after blast, deep inside of my tush.
“Now making him suck it out of you,” Janie s
aid with that big, glowing smile.
I crawled up and pressed my ass down on his face. Janie helped to spread my cheeks, and then Richard began to suck. I heard him gasp as his load was finally sucked out from my hole.
“Swallow it, bitch boy,” Janie said. She had a hand on my shoulder.
We watched as Richard swallowed his own cum, then we both giggled like little schoolgirls. It was fun. We both gave him a spank on the ass as he stood up. Then, once he was gone, we started laughing and rolling on the bed together, like old best friends. And it felt like we were old best friends, even though we’d only been a couple for three months and a couple of weeks.
“This is the best vacation ever,” she said. We kissed.
“I’m just glad to be here with you,” I said. “Am I allowed to look through that bag now?”
She grinned. “I know that you already did,” she said. “But feel free to go and pick out an outfit for tomorrow. I’m thinking we’ll go to another temple, and then maybe we can check out that club that we walked by earlier. I bet we can skip the line and get free drinks all night.”
“Sounds like fun,” I said. We kissed again. Every couple has their thing. This was just our thing.
THE END
SHE CAN TAKE IT
Bill has a good thing going: every weekend, his twin sister has all of her friends over for a slumber party. They stay up late drinking and gossiping about boys, and usually, by the end of the night, there’s one girl with an itch that needs scratched—and Bill is the only guy around to scratch it.
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