Rhianna, The Boy Next Door

It's been a few years since I have posted anything. I have not stopped writing, but somehow lacked the desire to share. Perhaps after posting this I will post more of those stories you have not yet seen! Feedback helps! - Tawny

Rhianna, The Boy Next Door

by Tawny Suede

Chapter 1 - Introductions

My name is Mark Drake. Glad to meet you.

I'm in my mid-forties and single. Well, technically I'm divorced, but my one marriage was in my early twenties and was very brief. I'm reasonably fit. I run every morning before I go to work and I watch what I eat. I have gray hair but still a very handsome face and perpetual stubble. Yeah, I could shave completely but the women seem to like the rugged look. They are also attracted by my nice income. I don't flaunt it but I live on my own in the suburbs and I drive this year's model Mercedes as well as always wearing very nice suits.

This particular story started with a strange email from my next door neighbor Shelly. I've lived in this house for the past fifteen years. Shelly and her husband and their son Ryan moved in about two years after me. The husband moved out about five years after that. Shelly would have been about thirty-five at the time, and Ryan just eleven. Ryan took the split hard at first but eventually adjusted to seeing his dad a lot less.

Over the years I've helped with odd jobs at Shelly's house and helped Ryan with his home work or tossed the ball with him in his younger years. Shelly has cooked me dinner many times. We've occasionally gone out on dates together and I've even fucked her a few times when Ryan was away for the weekend with his father. But it was never anything serious between Shelly and me. I knew it and she knew it. We both knew that it was just a bit of fun between friends, and to scratch an occasional itch.

Shelly just wasn't my type. What was my type? Well, I've always considered myself to be straight, but I guess you'd really have to call me bisexual. Oh I have no interest in guys, as guys. But I definitely preferred my dates to have dicks. Yes, I lusted after gals with a bit extra in their panties. Crossdressers, transvestites, transsexuals... whatever you want to call them, or however they labelled themselves is fine with me.

Weekend nights I was usually downtown on the gay strip hanging out at the bars that had drag shows, or were simply known for the number of transgendered gals who hung out there. Being handsome and well dressed I had very little trouble finding company for a few hours, whether it be at a local hotel room, or if I felt comfortable enough taking the gal back to my home, which needed a lot of trust on the part of both of us.

Shelly knew my preferences. But she was a great looking gal. And sometimes one or the other of us was feeling down, or feeling great and was in the need of a good fucking. So we fucked. We just tried to keep it discrete from her son Ryan.

Oh, yes, the email....

A few months back Shelly had started a new job that required her to travel out of town for several days at a time. Ryan was now nineteen and would be going to college soon. He was old enough to stay home on his own and he was generally pretty good at looking after the place and not having parties, etc. So she trusted him but he knew he could call me if he needed anything.

Shelly was going to be away for ten days this time, the longest trip yet.

Two days after she left I received an email from her which was very unusual. It said, "Mark, my niece Rhianna will be staying at my place for a few days while I am gone. Could you be a dear and take her out on a date on Saturday night? Much appreciated, Shelly xxx"

Why wouldn't she have asked me this in person before she left? Why was Rhianna visiting while she was not there? And why would she set up a date for her niece with a much older man? Something was not right, and I instantly had a suspicion as to what was going on.

But I played along and replied, "Shelly, I would be very pleased to entertain Rhianna on Saturday night. I am looking forward to it! Mark"

This was on Wednesday evening. Over the next couple of days we exchanged a couple more emails and we agreed that Rhianna would come over and knock on my door at eight pm on Saturday night.

Over the next few days, whether it be during my morning run, or when I pulled into the driveway in the evening or taking care of my backyard in the evening, I never saw any sign of the niece. Ryan would be outside at times and wave at me but we never spoke. He seemed awfully nervous and I was pretty sure I knew why.

I was fairly certain that Ryan was Rhianna.

Chapter 2- Ryan

At least the meager evidence so far pointed to Ryan being Rhianna. Ryan was probably using his mother's email account to send the emails to me and instantly deleting them so that his mother knew nothing about them. He would know I would do most anything for my friendly neighbor, his mother.

And Ryan and Rhianna sounded very similar. Many crossdressers chose girl names close to their boy names, when they were starting out.

Of course, I had never suspected Ryan liked to wear female clothing, or thought of himself as female at all. But then, how well does anyone really know anyone else, especially across generations. As I said, I am in my mid-forties and Ryan is nineteen.

I barely noticed Ryan when we first met. I would chat with Shelly or his father over the back fence and sometimes at a neighborhood barbecue. Six year old Ryan would be playing with the other neighbor kids in the background. When Shelly split up with her ex, I would sometimes help Ryan with his homework or play catch with him; surrogate father stuff. He was always polite and called me Mr. Drake. When he became an adult I told him to call me Mark, and he tried, but it always seemed awkward for him, so he would always fall back on calling me Mr. Drake.

Over the past couple of years we had very little interaction. He was never very athletic and due to the courses he was taking he had changed high schools. So he had lost most of his local friends. Yes, they still lived in the surrounding houses, but lack of contact during the school day meant that they drifted apart. Ryan started to become withdrawn. We still said hi over the fence when one of us was cutting the grass or doing other outside activities but he no longer needed my help with school work.

Ryan had very few friends it seemed. His best friend was a girl named Debbie who lived a few miles away, but had a car. She often picked Ryan up and they went off and did whatever teenagers did together these days. Sometimes just the two of them and sometimes with one or two other girls. When I asked, Shelly told me that there was nothing romantic between them. They were a guy and girl who were friends. She was not Ryan's girlfriend and in fact, of the two of them, Debbie took the lead most of the time when deciding what they might do.

Did I suspect that Ryan might be femme, or gay? The thought had not crossed my mind until now. But thinking back, I realized that many times I had caught Ryan looking at me when I had not suspected. Particularly on occasions when I might be in the back yard in my swim suit by my pool, or using my weight equipment that was in the car porch where I never parked the car. I had spotted him watching me from his bedroom window a few times, and quickly darting behind his curtains. Or he might engage me in conversation across the back fence while my shirt was off and sweat was dripping through my chest hair after I had finished a workout.

Thinking about it brought back other instances when Ryan might have been checking out my body. And yes, I think I did spot him a few times checking out my junk in my swim trunks and then averting his eyes.

Despite us being careful over the years, I am pretty sure that Ryan knew that his mother and I had fucked once in awhile. His mother certainly had boyfriends over the past several years, and some had stayed over night. But no one had stayed in Shelly's life more than a few months. Shelly and I had our fuck buddy sessions when Ryan was away, but while the boy was not a genius there were enough clues over the years that he should have figured it out.

Similarly, he probably had observed enough of my dates over the years to realize that I was at least bisexual. Most of the gals that I brought home left in the early hours, but some hung around for breakfast and even a morning swim in the pool. Sometimes they presented well as female even in the morning or in a swim suit, but some of them looked very male in the morning light. That did not bother me at all. When we were fucking at night, I wanted the illusion of a female with a dick but I realized that my companions were male, or at least started off that way and in the daylight they might prefer to be seen as guys. I respected that and that is one of the things that made me popular at the clubs. I accepted people for who they are, not who I might like them to be.

Ryan might have seen a young guy hanging out with me by my pool and might have seen me give them a kiss goodbye as they left, and I'm not just talking about a peck on the cheek. If he had been watching for me to come home late at night, he would have seen me arrive home with an apparent female, and in the morning might see a guy depart in a taxi.

So I am pretty sure Ryan knew the type of gals I was dating.

And perhaps he decided he wanted to be one of those dates.

We would soon see.

Chapter 3 - Introductions

If it WAS Ryan, I decided to tease him a bit. On Saturday morning I saw him outside mowing the back lawn. So I put on some short shorts and went out and used my weights for ten minutes. I did not wear any underwear under the shorts and my package was evident to anyone who might be looking - peering over my fence for example. As I went through my exercises I glanced over but it was hard to tell if Ryan might be trying to get a look.

Next I changed into a tight swim suit and did a few laps in my pool finally ending up relaxing on a lounge chair by the pool. My wet suit definitely showed off my hard cock, kept hard by remembering the sweet young crossdresser I had brought home two weeks ago. Ryan did stop the lawnmower and we had a short conversation over the fence. He was definitely checking me out.

I had some work to do and so was inside the house for the rest of the day. Around four pm I heard a car door slam. I looked out from my kitchen window and I saw Ryan's friend Debbie pulling two large cases out of her car and taking them into the house next door.

I slowly did a clean up of the house. Not that it was dirty, but I straightened cushions and put various items away in cupboards. I also organized the kitchen. At seven I went upstairs and shaved and showered and put on the clothes I had chosen for the evening. While I was still upstairs I looked outside as Debbie's car drove away.

I continued with preparations for the evening as the top of the hour approached. At three minutes after eight my front doorbell rang and I opened the door to a vision.

"Hi, my name is Rhianna!" he said, smiling but not quite able to look me in the eye. It was definitely Ryan, but also delightfully feminine. His hand brushed some hair from his face. A very cute gesture.

"Hi Rhianna, you are in the right place. I'm Mark. Please come in!" Ryan stepped inside and continued to the living room. He had a delightful wiggle to his hips as he walked confidently in his three inch heels. He was wearing a white top above a tan skirt, and a short leather jacket that looked quite expensive. He also wore stockings (I love a gal in stockings!) and I could make out the outline of a bra beneath the blouse. He filled out the bra nicely, but I did not know what he had stuffed it with. Over his normally very short hair he was wearing a blonde wig with shoulder-length hair. It framed his face very nicely.

"You have a lovely house," he said. Ryan had been in my house several times over the years, but of course Rhianna had to pretend she had not. I took his jacket and placed it over the back of a chair.

"I have a bottle of wine open in the kitchen. Would you like a glass?" Ryan nodded, and led the way, which of course he could not have done if he had not been in my house before. A small mistake, but a telling one.

"Very nice," he said, as he took a sip after I had poured two glasses. His fingernails were painted red, to match his lipstick. His eyes were expertly made up, smoky and dark. His earrings were long and dangly. His ears were pierced, which I had never noticed before.

We wandered out of the kitchen and back into the living room where we sat in two chairs opposite each other while we enjoyed our wine.

Rhianna presented very well. It was obvious, to me, that Debbie had come over and helped with the makeup but Ryan's confidence in the clothes and walking revealed that he had dressed as Rhianna several times before. It's amazing what you do not know about your neighbors, isn't it?

Rhianna's voice was light and a bit higher than Ryan's normal voice. As we talked he did make eye contact with me regularly, but every once in awhile his confidence broke and he looked down.

If I had been just the average good looking guy next door and did not regularly date gals with dicks, Ryan might have fooled me into thinking he was a regular girl, for awhile anyway. But his adam's apple gave him away for a start. And I was well versed in spotting the slightly larger hands and the hips and other features that distinguished a male from a female. Interestingly, those subtle differences actually added to the allure of the crossdressers and other transgendered gals who I liked to spend time with.

After about twenty minutes I led us back to the kitchen to refill our wine glasses. As we took those few steps from one room to the other, I placed the palm of my hand against his back and I felt him shiver. He faltered a bit on his heels, but he paused so that the pressure of my hand increased and he moaned very softly.

As we sipped our wine he asked me about our plans for the evening. I smiled over the wine and told Ryan that I had decided we might be more comfortable not going out, and that I had decided to cook for us.

I saw him tremble a bit, and then smile. It was almost as if he was torn by the relief of not having to go out to a public restaurant, but also the desire to see how successful he might be at it. Of course, I had no idea how often he had been out in public, dressed, if at all.

I decided it was time to relieve his mind a bit. We had been wandering around the island in the middle of my kitchen. He was admiring this item and that as he sipped his wine. I waited until a moment when he had set his glass down, so that there were no accidents. I came up behind him, and put my arm around his waist. I pulled him back against my body. I brushed his hair aside and kissed the back of his neck. He moaned, enjoying the moment, which I then shattered by saying, "Ryan, I know this is you!"

His hands flew to his face, he hunched over a bit and began to sob.. I tried to turn him around, but he resisted briefly and then he pressed his face to my shirt and sobbed, "Oh, Mr. Drake! I am SO sorry!" His hands went to my shoulders as he cried gently against me. I let him sob for a full minute and then placed my fingers on his chin and tilted his head up.

His mascara was smeared a bit but his lipstick was unsmudged. So I did the gentlemanly thing, and I smudged it. I lowered my face and I kissed his beautiful lips. After a pause, he kissed me back.

No tongue. Not yet.

He stopped his sniffles, but again said, "I am so sorry, Mr. Drake. I should never have tried to fool you..." I stopped him by kissing the end of his nose. That evidently made it itch; he scratched the itch, and then smiled at me.

And at this moment, Ryan disappeared, and for the rest of the evening there was only Rhianna.

Chapter 4 - Rhianna

"Relax, Rhianna, I am a friend. You know that. I'm sorry, but you did not fool me. Not even from the first email. I knew who was messaging with me, and I welcomed you." She smiled at me as I said that, still trying to wipe tears from the corner of her eyes.

"Oh, Mr. Drake...."

"It's Michael, remember! Now why don't you take your purse into the bathroom and fix up your makeup.."

"Oh no," she cried. "I must look a mess!"

"Not at all," I said, and I kissed her on the forehead.

She frowned at that. "I'm not a kid!" she said, and then kissed me on the lips. "I'll be right back." and she walked to the bathroom, a bit of extra wiggle in her hips.

I pulled the fish out of the fridge and began to prepare dinner.

Rhianna was in the bathroom for about ten minutes. I suspected that perhaps she had called Debbie on her cellphone to give her a quick update. Rhianna's makeup was very well prepared. This told me that she was not totally dependent on Debbie in that area and so Rhianna had had a bit more experience at dressing than I had suspected.

Cooking the fish and rice and preparing a small salad did not take much time at all. Rhianna continued to sip her wine and made more animated small talk. She was smiling much more and giggling a lot. It might have just been the wine, but I suspected it was because she was relieved that she was not hiding Ryan from me. Yes, she needed to stay in character, but any small slips would be forgiven.

Just before everything was ready, I opened a second bottle of wine and reached for her glass. But she put her hand on top of the glass to stop me pouring. She stood in front of me and leaned in to me with her mouth open slightly. With this invitation, my mouth moved to hers and this time our tongues danced together as we kissed, this time with a bit more urgency. And her hand gently squeezed my hardening cock.

"Just so that you know it isn't the wine," she said softly. And she whispered in my ear. We looked at each other and each smiled with delight. I pecked her on the lips and said that dinner was ready.

She took a napkin and wiped some lipstick from my lips and then made a brief trip to the bathroom to repair her lips.

When she returned, I handed her a plate. But instead of going into the dining room, I lead her out the back door to the back patio where I had set a table with tablecloth and candles. I have a couple of tiki torches out there as well, which I lit, giving the table a romantic glow. It was a small table and so, although we were seated across from each other, we were still very close.

I topped up our drinks again and we toasted, To the Evening Ahead.

As we ate Rhianna related how she has begun dressing in women's clothing. It was not anything she had thought about until she had met Debbie, and it was at Debbie's encouragement that she had first started trying on panties, and then stockings, and then going further. Although they were not boyfriend and girlfriend, they had fooled around with each other but from Rhianna's descriptions it seemed that the sex was mostly Debbie rewarding Rhianna for becoming more and more feminine.

Debbie had brought a couple of girlfriends in on their shared secret of Rhianna's dressing, and soon all four "girls" began going out to clubs in the evening, and eventually convincing Rhianna to go out to the mall with them. So long as she was in the company of the other girls, she felt safe.

As we ate, I would occasionally touch her hand with mine, or lay it upon hers briefly. At first she pulled back and eventually we were holding hands briefly between needing to raise forks to our mouths. I also felt Rhianna's foot running along my leg at times.

Debbie had been encouraging Rhianna to dance with guys when they were out at clubs. It seemed a sure way to get the guys to buy the drinks, she said. Rhianna had become comfortable interacting with others at the clubs, but she was not sure she was attracted to any of the guys. She admitted to liking being held by a larger man, but she did not have any feelings for anyone she danced with.