My Seduction into CD'ing & Gay Sex

Sliding off the cushions my dress and slip hems rode up my legs well past the top of my nylons.

"You'll need to be a bit more careful in the future if anyone else is around," he grinned at me, "That is really sexy flirting."

"I'm sorry," I mumbled and began to blush.

"Don't be sorry with me," he commented, "I love it! You really have lovely legs."

I felt flattered and loved hearing that from Mr. Ferguson. He led me through the house and to the stairs.

"We need to see how you navigate going up stairs compared to down them," he told me, "You are still walking a bit like a boy in high heels but I think we can cure that shortly."

I managed to get upstairs all the while knowing he was watching my backside and looking up my dress at my legs. It was a bit exciting for me.

In the bathroom I was about to close the door but he stayed with me.

"No, no," he admonished me, "I need to be your 'shadow' all the time to make sure you obtain the habits of a young lady if you are going to have that inside track on how they think."

As I stood before the toilet ready to hike up my skirt and lower my panties he was again correcting me.

"No, Alicia, not that way. Boys stand to piss, girls drop their panties below their knees and sit on the toilet to pee properly. You must always do it that way, too."

It was a bit embarrassing to turn and lower my silky panties down over my nylons, the sensation once again making me shiver in pleasure, and then sit there and aim my pee inside the toilet bowl.

When I had finished Mr. Ferguson had me softly tap my penis dry with toilet paper, like girls do to their pussies, before I could get up.

I was about to pull up my panties when he advised me to take them off as we needed to get another task completed. As he did so he was filling an enema bag with warm water at the sink.

"Get down on all fours on the large towel on the floor," he directed me. I then felt him lifting my skirt and slip up over my ass and draping them well up my midsection out of the way.

He greased up the nozzle, as I watched, and then moved behind me and told me to just relax and let the end of the nozzle slide inside my anus.

Easier said than done, I quickly realized, but with gentle persistence on his part he made me relax and the nozzle end slowly entered my nether channel.

Gradually, he eased the slippery hard plastic into me and then released the flow of water from the bag which he had hung on a hook behind the bathroom door.

"ohhh," I moaned gently as the water gushed down the tube and into me. As that was happening he kept slowly easing the nozzle in and out of my anus but never taking it all the way out.

Despite myself I began to slowly rock back and forth to meet the gentle thrusts he was giving me.

"I can see this is becoming enjoyable for you, Alicia," he whispered in my ear as he reached around me and stroked my now stiff cock. "Maybe you and I will want to do this often."

Soon I was feeling quite bloated with water and he eased me up to a standing position. Guiding me back to the toilet he had me sit on it but scrunch forward so he could deftly remove the nozzle from me.

The water shot out of me into the bowl and I felt instant relief. I was glad this was over, even though it was a bit of a turn on, since it was a bit humiliating.

Before I could get up, though, he had refilled the bag and bade me to wipe myself clean and then get back on all fours for him.

This time he had a different nozzle on the end of the enema tube and it was shaped like a cock.

"This will make it easier for you to accept the butt plug," he advised as he liberally greased up the false phallus. "It won't hurt you and will probably feel a bit nicer than the nozzle did."

With that he got behind me again and put the head of the false cock up against my anal opening. It took a bit of trying, on my part, to relax but finally he had managed to ease the head of the enema dildo inside me.

"ohhhhh," was all I could muster as he slowly worked in further and further inside me. Soon he had all six inches buried inside my ass and I was becoming accustomed to having it there. Then he released the water and I felt my rectum taking on another bag full.

As before, he began working it in and out of me as the flow entered me. I couldn't resist rocking back and forth to meet the thrusts and he began stroking my cock again.

"You're enjoying this, aren't you, Darling," he commented as he worked on me driving me to a fever pitch.

Soon I as filled with the other bag of enema water and also wanting to cum. However, he held me close and led me back to the toilet so I could void the contents of the enema.

After wiping myself clean and dry he had get back on all fours once more. I began to wonder how many times he would be giving me an enema.

He produce a metal ring with an inside diameter of nearly two inches. From somewhere he had ice cubes in his hand and quickly my hard-on disappeared and even my balls seemed to shrink.

"Good girl," he intoned and then quickly slipped the ring up my cock to the base and managed to get both of my balls through it, too, before I started to swell up again from his fondling. Now I had a metal ring surrounding my sensitive area and I learned it would prevent me from losing my hard-on.

"Perfect, Honey," he said softly, and then he fitted a leather strap around my waist. I was now quite curious about what he was going to do to me but knew better than interrupt him.

The leather waist strap had another at the very front that he pulled down and looped it through the metal ring and then closed the snaps on it.

From the back of the waist band was a second strap that was longer and could be pulled between my legs to the metal ring around the base of my cock and balls.

From the counter he brought over a pink cone shaped device. It had a bit of a rounded top and flared out to a couple of inches across and then nipped in to about a half inch in diameter below it and had a flat rectangular base.

Liberally greasing up the cone I realized this was the butt plug he was referring to earlier.

"Now, just relax and let it enter you," he said softly as he began probing my anus. It took a few moments and then the rounded tip entered me but would not go further. It was larger in diameter than the dildo and I wasn't sure it would fit.

"Just relax, it'll work, Dear," he whispered, "And will soon feel wonderful for you. This is the toy that will help you learn to walk exactly like a girl."

It took another minute or two and it was finally snugly in my ass. Surprisingly, it felt very nice.

He then held out a small piece of leather that he fitted around the base of the butt plug and it had two sides that hung down about an inch each with snaps on them. These he fitted around the strap that went between my ass cheeks and snapped them closed.

Now he had the butt plug in place in me and it would not come out until the snaps were released. At the same time the cock ring was keeping me hard and my arousal was a great surprise to me.

This day had been one of nothing but shocking surprises and I began to wonder how many more were in store for me as I moved to each plateau.

"Okay, Honey," he told me as he held out his hand, "You can stand now and put your panties back on."

I did as he told me and was a bit stunned to feel the butt plug moving inside me as I moved my legs to step into the panties. The look on my face gave away the sensations I was now experiencing.

"Almost feels like someone is gently fucking you, doesn't it, Alicia?"

"Ye, yes sir, I guess that's what if feels like," came my shaky reply.

"You'll like it and at the same time it will force you to walk like a girl."

He held my hand as I walked through the master bedroom, down the hallway, and traversed the stairs to the living room. My quiet sighs and slight moans reinforced what he wanted of me. I was astonished to feel this plug bobbing up and down inside me with each movement and wanted to walk more and more to keep it doing it.

"You're already walking more like a girl," he mused and then poured me a glass of red wine.

Taking my hand in his, as we walked back to the screened in porch, I felt like a girl who was slowly getting well fucked and loving it. I was transitioning into young womanhood.

"Here's a toast to you, Alicia, on becoming a young girl and tonight you will experience fully what it is like to be a woman."

With that we clinked our glasses, sipped a sip, and then he kissed me as his free hand managed to push the butt plug further into me and then ease it out. My moans were music to him and my knees visibly trembled inside my nylon stockings. I didn't think to question his comments about my experiencing fully what it would be like to be a woman.

Taking my hand he led me to the glider and he had me ease down softly onto the stuffed cushions.

"You don't ever want to sit down hard while wearing a butt plug, Darling," he told me, "It can really hurt."

I assumed he was right as just sitting down seemed to ease the plug further up my back channel and I squirmed a bit at the feeling of it. That didn't go without notice by Mr. Ferguson.

We chatted awhile and he inquired what I thought of the young girl's magazines he'd given me to read. He seemed pleased to learn I found them interesting and there were several articles I really thought might be fun to complete reading.

We held hands on the glider and sipped our wine as we chatted. Pretty grown up for me, but at 18 you can have certain drinks in our province. I felt like a young woman on a date and I was really loving it.

"Girls are sooo fortunate," I thought to myself as we sat there.

Eventually, Mr. Ferguson told me it would soon be dark and we needed to have our dinner. He was going to scurry into the kitchen and fix a salad and then we could team up on barbequing the steaks he had gotten to celebrate my transformation into a young woman.

A short while later he came back and asked me if I'd like to help with the barbequing of the steaks! I'd hardly nodded my head when away we went through the kitchen to grab the steaks.

He fired up the grill and showed me how to grease up the grill top so the meat would not stick.

"You need to always use something to grease up where you are going to put your meat," he grinned.

"Unless my mouth is wet and waiting for it," I grinned back and we smooched as we stood next to the barbeque. Before long he was thrusting the butt plug into my ass again and it was turning me on like crazy.

"I think we need to stop," I whispered in his ear, "Even though I don't want to. However, if you keep that up I'm going to cum in my panties."

We managed to control ourselves and finish cooking the steaks and then he took me back to the porch where he had somehow set the table and he then lighted a couple of candles. It made for a very romantic setting for our dinner.

We enjoyed our meal and he told me dessert would be special tonight. I was curious and hoped I was the dessert.

He poured us each some more wine, although I didn't need any as I could already feel the effect of my first glass. We sat there and sipped our drinks and chatted about a variety of things until he turned the conversation about my wearing only girl's lingerie, a dress, stockings, high heels, and makeup along with a wig.

I admitted I was loving it and his gift of the panties, the other day, had started the whole thing.

"I had hoped it would, Alicia," he said softly. "I've been wanting you for a long time and this is a great way to make you happy, you can learn what you need to find out about femininity, and maybe more."

"I suspect you plan for more in the plateaus you referred to," I commented over the rim of my glass as I smiled at him.

"Tomorrow you will be learning a girl's domestic duties. I want you to learn some basics about cooking, which your mother will love, as well as house cleaning, etc. You will wear a maid's uniform and I've another pair of high heels to go with the uniform."

"Wow," I enthused, "That sounds like fun. I'm really enjoying living like a girl."

"Great," he said as he looked at me from across the table. "Tonight you will learn even more."

As he said this I suddenly felt a slight buzzing in my bottom and it seemed the butt plug was vibrating.

I must have gotten a funny look on my face as Mr. Ferguson just looked at me and smiled more broadly.

"Does your butt plug feel nice, Honey?" he asked and suddenly the vibrations increased quite a bit.

It was all I could do to sit still in my chair without wiggling all over it caused by the butt plug.

"Wha, what are you doing?" I wanted to know and the vibrations got even more pronounced.

"It is a remote control that is tuned in to your butt plug, Darling," he smiled. "I think it must be feeling very good to you. Now let's try this," and so saying the butt plug not only vibrated but began to pump up and down inside my ass!!

"That's it, Alicia, just let it take over and give you a nice ass fucking. I'm sure you are loving it from the look of ecstasy on your face."

I was now holding onto the edge of the table as the butt plug took on a life of its own. It was vibrating strongly, so strongly one could hear it, and it was thrusting up and down inside me.

"Oh, o, oh, um, M, Mr. Fer, Fergus-son, I, I'm go-going to c-cum!" With that I began flooding my pretty pink panties with my gism as the tool worked away on me training me to accept being fucked back there.

It took me a few minutes to settle down and he didn't reduce the vibrations or thrusting until he knew I was done cumming.

"Let's take you upstairs to the bathroom and get you cleaned up and into a fresh pair of panties," he told me.

Upstairs he gently washed me with a warm washcloth and then gently dried me and powdered my cock and balls before helping me step inside a fresh pair of sheer pink panties and snug them up in place.

I was still a bit weak from what I'd just been through and also wondered if the wine was having an effect upon me, too.

"Come on down to the family room," he told me, "And we'll watch some TV after I clean up our dishes."

I went downstairs with him but insisted on helping clean up after our meal. The butt plug was now silent in my ass but I was constantly aware of it and my cockette was remaining hard thanks to the cock ring he had me wearing.

With the remnants of our repast put away, and all the dishes and other items washed and drying, he took me into the family room and had me sit on the sofa facing the large screened TV set.

"I've a couple of movies that you might enjoy seeing," he said and clicked on the remote. As soon as a picture came up on the screen he clicked another remote and the video player began.

It showed a guy and a gal necking in her living room. He was trying his best to get his hands up her skirt past the tops of her nylons. However, she pretty successfully fended him off and allowed him to open her blouse and eventually unhook her bra. Soon they were kissing and he

was feeling up her breasts and then suckling on them. I found it stimulating to watch as I'd never seen a movie like this but had heard of X rated movies.

Mr. Ferguson was now sitting next to me with an arm around my shoulders as we watched the video. He was holding me close and I was loving the feelings of being cuddled by a man.

"Here comes the better part," he whispered in my ear and then kissed me. "Watch what happens."

The couples necking had become more heated and she had unzipped his pants and was slowly jacking him off as he suckled on her breasts. He was still trying to get his hand up under her skirt and she was twisting to and fro trying to fend him off.

Finally, he managed to get his hand into her panties and began feeling her up more but, all of a sudden, he stopped and looked at the precious platinum blonde with total surprise on his face.

"What's this?!" he wanted to know and pulled her skirt and half slip all the way up to her waist. Revealed to the camera was more than just the tops of her nylons, garter belt, and sheer white panties, but she had a cock, too!

"I've been afraid to tell you," she muttered and began to blush. "I want you as my boyfriend but how could I tell you I am a boy, too?"

"It, it's beautiful," he whispered and pulled her cock out of the leg opening of her panties. "I think it is great you have a cock, Darling!"

Her head fell back and her eyelids fluttered as he lowered his mouth to her cock and began sucking her off.

It wasn't long before he had her panties off, had shucked his jeans and shorts, and was fucking her with long hard strokes as she wrapped her arms and nylon clad legs around him and urged him on.

By this time I was fondling Mr. Ferguson's cock, which I had freed from his trousers, and his hand was up under my skirt feeling me through my panties.

"You are staying hard, Sweetie," he murmured to me between kisses.

"So are you, Darling. I need to do something for you, and lowered my head to his cock.

However, he had other plans.

"No, no, Honey, let's go upstairs to the bedroom. We can watch more of this movie, and others if you want, later. Right now I want you."

I offered no resistance as he led me upstairs and fondled my ass on the way up. In the bedroom he helped me out of my dress and slip before bringing me a floor length sheer chiffon nightgown in a delicate pink.

Soon I was standing before him in the soft light of his room wearing a beautiful nightgown, my bra and inserts, panties, garter belt, nylons, and high heels. I had already forgotten about the butt plug and was eager to get my hands on his cock!

He quickly stripped nude and then embraced me. I loved seeing him nude! Quickly we were necking and stroking each other and I was about ready to erupt. He could sense it and suddenly stopped and told me we needed to take the butt plug out as it was time.

He undid the harness from around my waist and unclipped the wrap holding the butt plug. His easing it out of my ass suddenly had me feeling like I was really missing part of me. Then the rest of the harness was removed from me along with my dear pretty panties.

The metal cock ring he left in place and I didn't ask.

Taking me to the bed he had me lay down on my back with my head on the pillows. Then from his nightstand he produced some lubricant called "Anal Ease" and quickly slathered it all over his cock. Now I realized what he meant when he said I would soon experience fully what it was like to be a woman.

I kicked off my high heels when he lifted my legs apart and I felt him nudge my anus with the head of his cock. By this time I wanted what I knew was coming. I wanted to be just like the he/she in the movie we'd just been watching.

"Oh, ohhhh, Mr. Fer-ferguson, You, ohh, are soo b big," I muttered as he slowly worked he head of his cock in my ass.

"I hope it isn't hurting, Honey," he whispered, while kissing and licking my ear, as he kept easing more and more of his dick into me.

"No, no, it's a bit, uncomfort..... ohh, no, I kind of, li-like it," I moaned as he slowly but surely pushed his cock further into me. The butt plug had prepared me well for this.

Then he slowly withdrew it most of the way and then slid it back in. Soon he was thrusting in and out of me rapidly and all I could do was wrap my arms and legs around him and try to work with him. It seemed I was constantly moaning and wanting more.

"Ohhhh, fuck me, fuck me, make me your girl in all ways!" I screamed out not caring if the neighbors could hear us or not.

"I knew you would like this," he whispered in my ear as he was tonguing it turning me on even more. Then he gave me a deep French kiss and I felt my cock rubbing between our tummies as he kept on rapidly fucking me.