Terry's Tale

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Leslie helps Terry fulfill 'his' desires.
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It still amazes me that people would pay money to see me naked! All through high school I was a complete outcast. A short, skinny boy with a high pitched voice will never fit into high school cliques. Now, just a few years later, there is a website on the internet that featured little old me!

The website was all Leslie's idea, I have been living with her for over a year. She 'picked me up' at a gay pride parade of all places, we have been together even since. Our relationship may seem a little weird to some, we have a bit of an age difference. I am 21 and she is 46, which makes her older than my mother. And the fact that we are both bi, but lean toward gay doesn't help.

Before I forget, my name is Terry. I stand 5'5" and weight just over 110lbs. My hair is dusty blonde and shoulder length. I have a few odd features for a guy, a swell to my hips, an almost unnoticeable adam's apple and my facial features. I have fuller lips, a softer jaw line and my nose is cute unlike most guys.

Leslie is a very pretty lady, she is tall, almost 5'11". Her weight, if I had to guess, would be about 150lbs. She wears a 36C bra, I know because I have worn them before. Her hips are too wide for me to wear her pants or skirts. She has shoulder blade length dark brown hair and matching brown eyes.

I believe what attracts me to her is the feeling I get when she is near. When I am around her, I feel safe and protected. She has a way of taking control of any situation. The fact that she is by far the breadwinner in our home may have something to do with that too. I am a part-time waiter in a trendy, semi-fast-food restaurant and she is the Director of the IT Department for a large local company.

Early in our relationship, Leslie asked what sorts of things I had done sexually before meeting her. I openly shared all of my sexual experiences. Most of them were with men, older men. The younger guys seemed to have no interest in me at all. And the two girls I had sex with turned into disasters. I kept falling out! But those two girls taught me to eat pussy!

Leslie seemed most interested in my encounters with Ralph. Of all the men who have fucked me, Ralph is my favorite. We had fun while we fucked. He was my parent's neighbor and he broke my 'cherry' before I graduated high school.

+++

Ralph came up to me one day while his wife was away and invited me to lunch. As we ate, he casually asked if I was a virgin. At the time I was and I answered honestly. He asked if I liked girls, again I answered honestly. I told him I didn't know, I found both boys and girls attractive. He was so cool and said that a lot of kids my age are confused about their sexuality.

He went on to question me about what sex I thought about when I masturbated. At this point I got a little nervous, but answered that boys filled my fantasies. Ralph dropped that subject and began to compliment my body. He said I looked so firm and my skin looked so soft, and that he thought I was sexy. This embarrassed me a little, here was a grown man calling me sexy. But the attention he was pouring onto me was addictive and I began to flirt with him.

When I finally asked if he would like to touch me, he readily agreed but suggested we move to the living room. As we sat on the couch, his hand touched my thigh and a spark of lust shot through me. Ralph squeezed the top of my leg then slid his hand under so his fingertips were touching the hem of my thin white nylon shorts. Ralph asked if he could touch my stomach, he said he hadn't seen a stomach that tight in a long time. I raised my shirt and leaned back a bit, his hand began to caress my skin. I was in heaven.

He touched my hand holding the shirt and knew what to do, I raised it up and over my head and dropped it on the floor. He lowered his head and sucked on my nipples while exploring all over my upper body with both hands. Before long he was tugging down my shorts, when they got to about mid thigh, he pulled away from me and stared at my white cotton man-style briefs.

I asked what was wrong and he explained that someone as pretty as I was should not be wearing underpants like that. He took my hand and led me to his daughter's room, she was at away at college. He opened her panty drawer and pulled out a pair of pink satin bikini panties. Holding them on a single finger, he told me pretty boys should wear pretty panties.

Not wanting to miss this chance to finally have sex with someone, I quickly dropped my drab cotton shorts and took the frail garment. I stepped into them and when they were situated on my hips, Ralph smiled proudly. He took me back in his arms and I rose to my tip-toes as he kissed me deeply. His hands dropped to my bottom and he squeezed my cheeks through the panties. I reached between us and touched the hard bulge in his pants. As my little hand wrapped around that big piece of meat, I squeezed it and sort of jacked him off through his pants.

He broke our kiss and led me to the bed. He placed his hands on my shoulders and pushed as he sat down. I was on my knees between a man's legs, staring at a huge bulge and I knew exactly what I was going to do. I reached out and undid his pants. He stood up a little so I could pull them off of him.

When he was seated once again, I reached out with a shaky hand and wrapped my fingers around his rock hard cock. I lowered my head and began to lick it. I then took it in my mouth and began to bob up and down. When it was covered with a thick layer of my saliva, he pulled my head off and picked me up in his arms. I was laid down on the bed and rolled over onto my tummy. I got on my hands and knees per his request, he pulled the panties off and licked my little brown hole!

Oh my god! Fireworks went off in my head! I never thought being with another person would be this good!

He lapped at my ass for quite a while, even dipping his tongue inside me! Kisses were placed all over my cheeks and back until he somehow wound up laying on his back on the bed. He sort of moved me on top of his face, I was facing his feet and couldn't keep my eyes off of his cock. I bent forward and took his cock back in my mouth as he started licking and kissing my ass again. We ate each other like that for only a little bit until I felt his cock swell in my mouth. As soon as that happened, he pushed me off of him and told me that he was going to fuck me before he came.

Ralph rolled me onto my back and pulled me to the edge of the bed so my butt was hanging off the end. He grabbed my ankles and lifted them onto his shoulders. Reaching down he aimed his dripping cock at my sopping wet hole and slowly pushed.

When the head of his cock passed my tight ring of muscles, I won't lie, it hurt like hell. But the pain passed quickly and was replaced with a strange feeling. My body felt full, almost bloated. I was just about to ask him to take it out when he pushed a little more and then a little more. That full, bloated feeling faded and I felt sexy and horny. I wanted more!

I squeezed down on his cock, this must have let him know I was alright. He kept pushing until I felt his balls against my cheeks. I was writhing around on the bed as looked down on me. I wanted him to fuck me! I needed him to fuck me! I openly begged him to fuck me! And fuck me he did!

He drove that hard monster in and out of me at a furious pace! The bad part was that it didn't last long enough. He pulled out quickly, jumped up on the bed and straddled my chest. Taking his cock in his hand he pulled on it only a few times until a large wad of cum shot out of the tip and drew a line from my chin up past my hair. I opened wide for the next shot and he aimed perfectly. I felt his cum strike the roof of my mouth and then drain down onto my tongue. The last blast started on my nose, passed over my mouth and continued down my chin.

He watched closely as I moved my tongue around, treasuring the taste and feel of his cum. Finally I closed my mouth and swallowed.

That was my first visit to Ralph's house. There were many more after that. I discovered that he liked to have me dress up as a schoolgirl. He would play the principal and we would act out an entire scene of me being a bad girl. He would spank me, and then finger my ass. I would suck his cock. And we would always wind up fucking until he came all over me.

He always called me a 'bottom', I just smiled at the time even though I had no idea what 'bottom' meant. I was fucked several more times before it dawned on me what that word meant. To sum it up, I have never had the urge to put my little cock into anyone, but I am totally into being fucked by others, always on the bottom.

+++

In addition to my sexual encounters, I also shared my biggest fantasies with Leslie. When I finished telling my top three, she said that they all began with a common theme, exposing myself while dressed as a girl. She sort of teased me about the influence that Ralph had had on my life. With this information and my willingness to follow her lead, we went on a shopping spree, it was the most fun I have ever had! We wound up buying three outfits, all of them were feminine, short and very sexy.

Leslie must have known I wasn't quite ready to walk up to someone and flash myself. The following day I wore a pair of tight, white cotton, stretchy short-shorts, matching half shirt, white cotton ankle socks and cute white tennis shoes. Underneath I wore a white lacey thong and matching bra that clipped in the front. Even with an A-cup, the bra looked empty, but that was the look Leslie wanted. My hair was pulled into two ponytails and held in place by poofy white scruchies. All that white material really made my tanned skin stand out! The final touch was a bit of make-up. Leslie applied hot pink lipstick, lip gloss, black eyeliner, mascara and just a touch of pink rouge. I had played with girls clothes before, but I never looked that good! I felt wonderfully horny! My little 3" cock was rock hard.

Once dressed, she led me to our backyard. We live at the top of a cul-de-sac, so our backyard is huge. Leslie had it professionally landscaped and it is surrounded by a privacy fence. We have four big shade trees in the corners and a pool off to one side.

After the camera was set on the tripod, she took hundreds of pictures of me. Leslie helped with the poses until I got the hang of it. I then slowly stripped, piece by piece. I couldn't stop smiling the whole time, I felt so free and happy and loved! When I was completely naked, she had me pose in different positions all over the yard. We finished off with me swimming naked in the pool. Leslie captured everything with her camera.

As soon as she stepped away from the camera and sat in a lounge chair beside the pool, I pulled myself up out of the pool onto the wall opposite Leslie. It had taken everything I had to keep from jacking off during our photo shoot. I lay back on the warm cement and pulled my feet up onto the gutter ledge. I closed my eyes against the bright sun and reached for my cock.

My cock is pretty thin and only 3" long. Each of my balls are almost as big around as a quarter. I have always kept my light brown, pubic hair trimmed short, I heard that will make a cock look bigger. This didn't work in my case. But I think it looks cuter with short hair than with a big bushy mound.

I placed my thumb on top, just below the head of my cock and my index finger beneath. I held my finger still and rubbed my thumb back and forth. In no time at all, I was writhing on the cement and three spuirts of cum erupted from my cock. I lay there for a while to catch my breath, enjoying the feeling of the warm cum on my skin as it ran down my sides.

Later that day, we sat in her office and examined all of the pictures she had taken. Seeing myself dressed as a girl was a little shocking. Surprisingly, I looked hot! And Leslie thought so too. I told her that I thought the pictures of me completely naked except for make-up and scruchies in my hair looked really weird! It was like seeing a boy, but with a girls face! No body would want to see someone like that!

Leslie corrected me by browsing through the internet until she found pictures of boys dressed as girls! There weren't very many of these sites, especially when compared to similar sites featuring girls. And the sites we did find had models that were far from cute.

After several hours of looking at porn on the internet, we were both completely aroused. Leslie had plans for the evening. That night she introduced me to chat rooms. She paid a small fee to get us enrolled on an adult chat site. As she set up my profile, she suggested I go put on something sexy.

I didn't hesitate and scampered to my room. I dug through my drawers for a minute before pulling out my tight, pink cotton teddy. It is really high on the hips, has a thong back and lacey coverings for my "boobs". I slipped on a pair of 4" clear acrylic sandals and walked as fast as I could back to the study.

Leslie was in the bathroom getting undressed. When she had stripped naked, we quickly made up our faces again and re-did our hair. With a dash of perfume, we headed back into the study.

We set up a profile saying I was a sissy boy looking for a daddy. I couldn't help but giggle. She also uploaded one of the pictures we had taken that day. The pictures showed me from the front, I was toying with the shorts, exposing the straps of the thong beneath. The lump of my little cock was obvious under the tight white fabric.

I wasn't a great typist, so as we entered my first chat room, Leslie typed what I said. She taught me chat room manners: when entering a room you say hello, never use the abbreviations so many others use and always read their profile before chatting with anyone. She showed me the list of the people in the room and we browsed through their profiles while waiting for someone to contact us.

It didn't take very long at all. Someone called daddy1032, or something like that, IM'ed me (I know some of the chatroom lingo now). The first thing he asked was if the picture was real, I still get that to this day! Anyway, I told him that it was, we took the picture in our backyard that afternoon. Of course, he asked for another picture.

Leslie said this was my chance to expose myself someone. At that moment it dawned on me that I could send him a picture of me naked! Oh my god! I was so excited! We browsed through the folder until we found one a little more revealing, it showed me from behind, bent over at the hips wearing only the thong, tennis shoes and socks. My tan lines were hidden under the thong, I tan in a thong, my cheeks looked really good in that picture! My back was arched and the globes of my butt faded gracefully into my thighs. My legs looked really good too! Because Leslie had me point my toes together, the muscles of my thighs and calves were really defined.

I was rubbing myself through my teddy even before Leslie hit the send button. This was it! I was exposing myself to another person while dressed up as a girl! This had been my fantasy for so long, and now, thanks to Leslie it was coming true!

Daddy1032 replied almost immediately and offered to be my daddy. We began to chat back and forth. Before too long our conversation turned into cybersex! He was playing the part of my daddy, I was his 'daughter'. The scene he set up was him coming home from work after a hard day and me greeting him at the door ready to please him.

I had my hand beneath my teddy and was jacking off wildly! Leslie told me to hold off for a minute, she pulled a little box off of the back table and plugged it into the computer. A few menus popped up and she filled in boxes. As she typed she told me it was a webcam and we could show daddy1032 what I was doing while chatting with him. I was way too horny to say anything except yes.

Leslie got back to daddy1032 and told him she was there to type for me. She then welcomed him to watch me on my webcam. He eagerly accepted the invitation and a few seconds later, the webcam was on and we had confirmation that he was watching me. I smiled and waved to him and said hello. Leslie informed me that it didn't carry sound, only the picture.

Daddy1032 said, "Wow!". He told me to stand up and turn all the way around so he could get a good look at his 'daughter'. I stood and spun around on my toes, not being able to wipe the smile off of my face the whole time. He then told me to turn around and bend over. I turned and bent over, sort of facing Leslie.

Leslie was typing with one hand and diddling her clit with the other. Her nipples were standing out proudly on her big boobs and a thin layer of perspiration covered her skin giving her a shine. I could smell her sweet scent in the air and it was making me even hornier!

My 'daddy' told me he was playing with himself as he looked at his 'daughter's pussy'. I wiggled my butt a little and reached back and grabbed my cheeks and squeezed them.

Leslie loved that, she told me I could strip all the way if I wanted to. I thought about that as I continued to squeeze my cheeks and spread them apart for my 'daddy'. With a smile on my face, I reached between my legs and pinched the crotch with my thumb and finger. There were three snaps, I took my time and teased 'daddy'. As the last snap popped, the front of the teddy fell and the back jumped above my hips.

I felt so nasty and sexy! My little cock was dripping my juice and I couldn't stop grinding my hips if I wanted too. It was a HUGE turn-on to know there was a man somewhere beating off while looking at my naked bottom and little sack of balls.

I stood up straight with my back to the cam, reached down and grabbed the sides of the teddy and quickly pulled it up and over my head. As I dropped it to the floor, I knew I would do this again. I was safely exposing myself to someone else and I loved it!

Bending at my hips, I wiggled my butt then reached back with both hands and spread my cheeks wide. I told Leslie to tell daddy1032 that this is where his hard cock should be, buried deep inside me. When she finished typing, I began rubbing my little brown hole with my fingertip.

Leslie told me that he was about to cum. Quickly before he came, I rammed my index finger all the way into my ass. I stood there in front of the webcam and fucked myself with my finger until Leslie told me he had cum. I withdrew my finger, turned to face the camera, bent down so my face was all he could see and blew him a kiss.

That night, Leslie and I fucked and sucked until we were both completely exhausted. We began with a 69, I love to suck on her clit and finger her pussy. And that night she was so wet that my entire face was drenched when I came up for my first breath. She says that sucking on my cock is kind of like sucking on a really big clit, I have always taken this as a compliment.

Just as I was about to cum, she pushed me off of her. I rolled onto my back and gave her my best pouty look. She hopped off the bed and pulled open our drawer of toys, she pulled out the black leather harness and long pink dildo. Smiling at me she slid the long pink shaft through the harness. Leslie can read me like a book, she always knows exactly what I need.

As she positioned the harness so the nub on the inside rested against her clit, I couldn't help but admire her. She was so beautiful, especially when she is horny and feeling nasty! When the harness was arranged, she grabbed the lube and stepped toward the bed. I slid to the edge of the mattress and let my butt hang off the edge. Grabbing my ankles, I pulled my legs wide open and spread wide. She poured an ample amount of the liquid lube all over my cock, balls and down the crack of my ass.

"Want it rough tonight, slut?" she asked.

"As rough as you can be, big boy!" I giggled happily.

Leslie knows I like to be fucked roughly and plays the part. With her free hand she smeared the lube all over. Grabbing the dildo, she aimed it at my hole and let it tap against me.

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