Rhianna, The Boy Next Door

Yes, at Debbie's encouragement she had let them kiss her, and had begun to enjoy the physical sensations, but she had no desire to have an extended kissing session with any of them, although again, Debbie had insisted that Rhianna have a few makeout sessions with guys in the back seat of her car. Debbie had picked out suitable guys at the gay clubs that she took Rhianna to.

As we finished dinner, Rhianna reached for her purse and pulled out a package of cigarettes and a lighter. "Do you mind?" she asked.

"I didn't know you smoked, but go ahead. But just outside, please." I replied.

She lit the cigarette, inhaled and relaxed visibly as she blew a plume of smoke into the air. "Ryan doesn't smoke," she said. "But Debbie convinced me that smoking would help me relax as Rhianna, and she was right. She also says that if I practice enough, it can look quite sexy!" she grinned, and posed outlandishly.

She told me that she had actually seen me out at one of the clubs. When she spotted me at the bar, she was afraid I might recognize her, so she had convinced Debbie and the other girls to go to the far corner of the club where I was not likely to spot her. She had watched me, fascinated, as I chatted up and danced with the various girls in the club and had eventually left with a young crossdresser.

Rhianna helped me to bring the dirty dishes into the kitchen and we both tidied up the table outside as she continued.

Yes, her mother had at some point told Ryan about my predilection for transgendered girls. And when she was up late enough, she admitted watching out the window to spot my car when I came home to see whom I might have brought back. This was even before Debbie had coaxed him into his first pair of panties.

She said that from the moment I walked out of the club with the crossdresser, she had begun to fantasize that it was her that I was taking home.

Rhianna then reluctantly told me that Debbie had been having her practise giving blow jobs on a dildo and had finally convinced Rhianna to blow a couple of guys. Rhianna had not been eager to do this, but Debbie had threatened to stop taking him out to the clubs if he did not "advance" in his girl training. He had gotten to the point of passing in public, but now he needed to start passing intimately.

Ryan had no other real friends other then Debbie and the other girls, and he did not want to lose them, so he reluctantly agreed to this next phase of his journey.

It was not my place to tell Ryan, but it seemed to me that Debbie was just manipulating him for a laugh and a giggle. She sounded like a woman who just liked to dominate a guy for her own kicks!

Rhianna said that though she had been reluctant, she had found she quite enjoyed sucking the first real dick that Debbie found for her. Debbie approached the guy in one of the gay clubs. They took him back to Debbie's car and Rhianna had sucked him in the back seat, with Debbie watching from in front. When the guy had been ready to cum, Debbie had pushed Rhianna's head down fully and made sure the guy came in Rhianna's mouth. And had made sure that Rhianna had swallowed.

As she told me this we were standing out back, the dishes all tidied, as Rhianna finished a second cigarette.

"I've blown two other guys since then," she said. "They both told me I was pretty good." she smiled, "but I'm not really sure I am into that."

Chapter 5 - Intimacy

We went back inside, holding hands. I put on some soft music and we sat on the couch, very close. Our sides were touching and my arm was around her waist. There was no doubt as to where the evening was heading.

.I told her that I really liked her look, from the wig right down to the stockings and three inch heels. She smiled as she said thank you and then reached down to take off the heels. "They are killing my feet!" she said, laughingly.

I kissed her and our tongues said hello to each other for a minute, before she drew back. "That was nice!" she said. "I've been wanting to do that for awhile now!"

She said that as Ryan she had had a couple of fumbling attempts with girls, and was not a virgin. She'd had her own cock sucked a few times and had fucked a couple of girls. She'd liked those experiences and wanted more. But she had never fucked Debbie. But she blushingly admitted, Debbie had started fucking her.

Debbie told Rhianna that the next progression as a woman was for Rhianna to get fucked by a guy, but she knew he would have to work up to that. Debbie had a strapon harness and a few different dildos, and over the past month she had been fucking Rhianna in the ass, to get her ready for the real thing.

"Is this something you really want to do?" I asked her. She shrugged a bit. Earlier she had whispered in my ear that she wanted me to fuck her, but I really wanted to be sure about this.

"I think so..... yes! I don't know if I ever want to be a woman, but the experiences I have had so far have been nice. I've enjoyed most of it. I don't think I'm gay, but I'm at least bi-curious, if that makes any sense!" As she said that, she leaned into me again for a kiss and this time she rubbed my cock aggressively through my pants. This time it was my turn to moan.

I was pretty convinced that Ryan had never had a gay thought until Debbie started manipulating him. And I suspected that once she tired of him, he might return to being a shy retiring nerd who had a hard time scoring with girls and was reluctant to put on female clothing again without someone dominating him. But at the moment Rhianna was having fun exploring her sexuality and I had no problem helping her along in her discoveries, so long as she never used the word no.

Rhianna was now aggressively kissing me, and was tugging at my belt. In moments she had the belt undone and was working at the clasp on my pants. I lifted my bum a bit and she managed to slip my pants down past my knees. Her hand slid into my shorts and she grasped my cock in her hands.

"You're wet," she smiled at me.

"That's what you've done to me, honey. I bet you are too!" I pressed my hand to her groin, but did not find her dick. She was tucked, Though she did groan.

"Not now," she said. "But I would like you to please me later!"

"We have a long night ahead of us, sweetie!" I said as I kissed her neck.

"Oh yes, that's nice!" she moaned as she grasped me harder and began to pump me slowly. "You're big! I have to see it!" She slid to her knees between my legs as I kicked off my pants.

She grasped my shorts and pulled them down. My cock sprang free and she licked her lips. Her lipstick was slightly smudged from our kissing. "This is the first cock I've sucked that Debbie hasn't watched!" And she lowered her head and engulfed the head of my dick in her mouth.

Much as I loved the feeling, I paused her briefly. I pulled my dick out of her mouth and looked her in the eye. "Your mother never finds out about this, okay? Never, ever! Even if you eventually come out to her and tell her everything else, you and I never had sex. Right?"

"Never ever ever, Mr, Blake!" she grinned. "Now give me that cock back!"

I released her head and she again took the head of my cock in her mouth. Debbie taught her well. She used her tongue. She used her lips. She sucked me. She teased under the head of my cock. She bobbed her head. I moaned appreciatively at the right moments, to let her know when she was giving me greater pleasure.

At one point she took me from her mouth and teased my glans with her fingers. "Debbie won't let me wear smudge proof lipstick." she said, looking me in the eye. Indeed her lipstick was now very smudged. "She says I have to appreciate my accomplishments? And I do. Look," she said, pointing at my cock which had lipstick smudges all over it. "I did that!" she grinned, and popped my cock back in her mouth.

A couple minutes later, my leg muscles tightened and I told her, "I'm going to cum!" Without taking my cock out of her mouth, she looked me straight in the eyes and took me as deep as she could and then furiously attacked the underside of my glans with her tongue. "Fuck, fuck, fuck!" I cried, and then shot five strong shots of jism into her mouth. She swallowed some of it then opened her mouth to show me a large load and then swallowed that as well.

Rhianna gave me a few licks to get the last of my cum and then sat beside me on the couch. She ran her fingers through my sweat soddened chest hairs as she lay her head on my shoulder. We rested there for a few minutes. I then suggested that she put her shoes back on and that we go upstairs to the bedroom for the next round. She preceded me up the stairs and I gave her ass a couple of spanks. She giggled at that and waved her bum provocatively at me.

Chapter 6 - The Climax of the Evening

I suggested that she freshen up in the hallway bathroom and then join me in the master bedroom. I used the ensuite bathroom to freshen up including brushing my teeth and dabbing on a bit of musky cologne.

Just as I came out of my bathroom, Rhianna entered the bedroom. She had refreshed her makeup and lipstick again. She helped me turn down the bed and then we embraced, kissing passionately and we further disrobed each other. It took only moments for me to be naked as I only had to remove my socks and shirt. But Rhianna took the opportunity to again run her hands through my thick chest hair and to pump my cock a couple of times.

I helped her out of her skirt and her blouse. I also removed her bra and discovered that she had two small bags of bird seed that had given her the illusion of tits. She tried to cover the nipples of her flat chest with her hands, but I pulled them back. Her chest was hairless. Either she was naturally that way or she had been waxed. I caressed one of her nipples as I pulled her to me, kissing her lovely lips. She shivered. We stayed in the embrace as my fingers found and unsnapped the catch on the side of her panties and drew them off of her. I was then able to find the material of the gaffe that she wore to hold her cock tucked back and I released it.

Her cock sprang free and was almost instantly erect. As we continued to kiss I toyed with the head of her penis. It was very slick with precum and she moaned into my mouth as our two penises pushed against each other. My hand reached back behind her to finger her asshole, but I encountered something hard and rubbery. She was wearing a butt plug!

She smiled at me. "Debbie has been fucking my ass for the past month. But I wanted to be sure I was ready for you tonight!" I move behind her and she bent over slightly. I pulled and twisted at the plug and slowly pulled it from her asshole. It was not large, but not small either. As it popped free, Rhianna giggled and then pushed her ass back so that my cock lay nestled in the crack of her ass. She raised herself up and, still rubbing my dick with her rump, turned her head for a kiss and then said, "I am SO looking forward to this!"

I picked her up and tossed her laughingly on the bed. I then made as if to leap on her and she screeched and rolled away. I flopped onto the bed and drew her to me. We kissed hungrily. My hand teased her prick briefly and then stroked her stockinged legs. "I love a gal in stockings!" I whispered to her.

She was still wearing her garter belt, stockings and heels. The perfect outfit for a gal who wants to be fucked!

I kissed her neck and moved down to her nipples, teasing them with my lips and tongue. I kissed my way down to her belly button and then moved down further. She was completely clean shaven I thought, and then realized there was no stubble. Debbie had waxed Rhianna completely this afternoon!

I grasped her dick and fisted it briefly before bringing it to my lips. I sucked her cock into my mouth and she grasped my head. "Ohhhhhh," she moaned. "That is so fucking good!" I bobbed my head a few times, but then she told me to stop. Puzzled I looked her in the eyes and she encouraged me to come up and lay beside her.

"Thank you," she said. "But tonight I just want you to fuck me. At least, for now!" She kissed my chin and nestled her head on my chest. She twirled my chest hair as she told me, "You are the first guy to ever touch my cock. Heck, no one has touched it in over a year, other than to try to cause me pain. Thank you."

"But tonight, I want you to fuck me!" I kissed her.

"Debbie has had me suck off a few guys and now she wants to watch a guy fuck my ass."

"You're okay with that?" I asked.

"Sure. Yeah. I guess." she replied, but no too convincingly. "She says she has a couple of guys picked out for me. They both know I'm really a guy. I think they're gay, or maybe just into gals like me..."

"You don't know these guys? Why would you..." I started to ask.

"Because Debbie wants me to. Because... well because I guess I don't really know what I want!" She took my cock in her hand and toyed with me. I was hard as soon as her hand touched me. "I told her I would do it, and she has been fucking me with a dildo to help prepare me, so it doesn't hurt when I do it for real, but I told her I wanted my first time with a guy to be special."

"I told her... I told her I wanted it to be with you. And without her watching!" She smiled up at me. Her lipstick was messed up again and her mascara was running a bit, but she was very pretty. I knew this was the boy who had grown up next door to me, but I also knew this was a pretty young woman who knew her mind.

Well, she was being deeply influenced and led by her "friend" Debbie. But in this she was certain. She wanted me to fuck her.

I reached into a side drawer and pulled out a few towels. Not very romantic perhaps, but I rolled her over and placed a couple of towels beneath us. If she was going to bleed, I preferred to not ruin the sheets. I also pulled some lube from the drawer.

As I knelt between her thighs I lubed up my cock. I also took a few dollops of lube and used my fingers to push the lube into her ass. She was tight, but not too tight. The plug had done its work. I wiped my hands on a towel and tossed it to the side of the bed.

I lay upon her, our lips met and we kissed passionately.

I whispered to her, "Say it. Tell me what you want!"

She whispered back, "Fuck me! I want you to fuck me!!"

I knelt back up. She raised her legs, presenting her ass to me. I held my cock and placed it against her rosebud. "Fuck me, Mr. Drake! Please! Put your cock in me and fuck me!!"

And I did.

I pushed and the head of my dick slid inside of her. She grunted and stiffened her back a bit. I pushed again and a couple more inches disappeared. Her face contorted a bit and I gave her a moment to get comfortable. Then she reached up and caressed my arm and nodded. I pulled back a bit and then pushed back in again. Most of my cock slid into her. She gritted her teeth a bit and said, "Keep going! Put it all in me!"

And I did.

With one more thrust, my cock was fully inside her. I paused again for her to get used to my dick, and then I pulled back slowly and thrust in slowly. Her hand went briefly to her lips and then she sighed and nodded again and said "I'm fine! That feels SO good. So much better than Debbie's dildo. Your cock feels so warm. So beautiful."

I smiled down at her and began to set up a slow rhythm of pulling out and pushing back into her. She shifted her position a bit. She tried to wrap her legs around my hips and I moved more fully above her. Now I was able to lower my head and kiss her. She was eager for my tongue, sucking it so hard that it hurt. "Fuck me faster!" she said.

And I did.

I was now rutting inside of her. My cock was going faster. Rhianna's hands were both gripping the sheets. Her body suddenly stiffened and she let out a delighted yell. "There! There! Oh, there! That's.... that's the spot! Fuck me there!" I had hit her prostate!

My pace was quite frantic now. Her ass chute was so delightfully tight. Every time I pulled almost all the way out and then rammed in again, her tight ass grasped the underside of my dick head. I was spewing precum into her ass, making her more slick. This both made it easier to fuck her and also more frustrating since she was no longer quite so tight and my glans was not as stimulated. Until I was fully balls deep in her. Then it was like she was milking my dick!

Rhianna's cock was also leaking precum continuously across her belly. I scooped up a pool of precum and used it to slicken her dick. She tried to thrust her cock in my hand, but she was impaled on my cock and not able to push. But that was no problem and I set about vigorously jerking her cock and twirling my fingers around the base of her glans. She groaned and pushed back against my thrusting dick.

"Oh, Mr. Drake! I'm going to cum! Stop! Stop! I want to cum at the same time as you!"

"Don't worry baby, I'm cumming too!" And I did! Just as Rhianna unloaded jets of jism from her dick, covering her chest and chin in thick white cream, I thrust deep into her ass and unloaded my own scum into her bowels. I pistoned my cock in her ass a few more times, ensuring my load was buried deep inside her, and then collapsed alongside her on the bed.

We were both panting hard. "That was amazing," she said. "Fucking amazing! It was never like that with Debbie. She's only ever fucked me from behind. But to be able to look into your eyes, to be able to kiss while your cock is inside me. Fucking amazing!" She kissed me tenderly and reached for my cock.

I stopped her. "I'm a bit messy down there. You're a bit messy down there too!" I said. Taking a towel I first wiped off the mess from my cock and then tenderly wiped her asshole. "Next time we do this, perhaps it should be before dinner." I grinned at her.

"Oh, I'm sorry! I didn't think..."

"It's okay sweetie," I said, kissing her on the tip of her nose.

I used the ensuite bathroom to wash off my dick and urinate. When I came back she was still on the bed, looking very dishevelled but lovely. Her makeup was a mess and her wig was crooked. She had kicked off the heels and was rubbing her feet. "They make my legs look great, but they hurt like hell!" she grinned. "I guess I should get dressed and head home."

I stopped her and kissed her again. "Would you like to spend the night?" I asked her. She nodded eagerly. "There are some wipes in the side drawer in the bathroom that you can use to remove your makeup. You shouldn't sleep in it. And you can put your wig on the dresser."

"But then... then I'll just be Ryan!" her lips trembled.

"Who you are is not what you look like," I said. "It's what's in here!" and I tapped a finger against her forehead. "You get cleaned up and I'll find you something to wear to bed!"

As I straightened up the bed, I heard her tidying herself up in the bathroom. It took ten minutes before Rhianna reappeared. Yes, she was looking very much like Ryan, but she had left the stockings and garter belt on, and had applied a light touch of lipstick. Without her wig her hair was very short and she now looked like a cute adorable boy. She blushed as I complimented her.

I handed her a nighty that I told her one of my past guests had left behind. She cooed at it and pulled it over her head, then ran her hands up and down her body. She stood in front of my full length mirror and posed in a couple of different positions. "It's lovely," she said and came over and kissed me on the cheek.

We climbed into bed and pulled a single sheet up over us. We lay facing each other and she came into my arms. We kissed tenderly and then she snuggled her head into my neck and we just lay there cuddling. After fifteen minutes or so she was almost asleep but rolled over the face the other direction. I moved behind her and spooned her, my cock semi hard and nestled against her ass. We both fell asleep.