Terry's Tale
Keywords: Tale, Terry's,
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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.
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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.
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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.
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Keywords: Tale, Terry's,