Date: Sun, 26 Nov 2023 18:06:57 -0700 From: Sissy Chanel Subject: It started with my best friends dad Please give generously to Nifty and support this awesome site. Help continue these stories being available free of charge. Disclaimer: This story is an erotic fantasy. The characters and events described are fictional. Any likeness or similarity between persons, places, products, or concepts is purely coincidental. If you are under 18, and/or offended by descriptions of homosexual activity or live someplace where reading such material is prohibited, don't read this. The following story contains strong language and explicit scenes of male-on-male sex, and cross-dressing. Please email me your comments to sissy Chanel, if you enjoyed reading, shot your load, or can relate to the story in any way. It means a great deal to me to get feedback from my readers. I will try to respond to every one of them. My email address is Sissychanel9@gmail.com This story is the copyright property of the author and may not be copied, used, or posted to any other websites without explicit permission from the author. Chapter one: All my life, growing up, I struggled to make friends. My feminine facial features, high cheekbones, and slim figure only made things worse. I was only 5'4 and that didn't help matters either. My slim thighs, slender arms, smooth skin, and soft hands were almost always mentioned in a handshake or hug. My slightly less-than-average-sized member isn't necessarily a gift from god. I only had one friend that I had while growing up. I met him on the swim team in Junior High School. His name was Billy. Billy always made an effort to hang out with me. The only real thing we had in common was being on the swim team, watching sports, and playing video games. He always found awesome video games and sports we could watch. Over the years our friendship developed. He was my only friend. I was at his house a lot either playing video games or watching sports. It wasn't uncommon for his father to join us in watching sports. He was a huge sports fan as well so we all had that in common. Billy's mother had died when he was young, so it was just him, his dad, and his older sister Tiffany. I never saw much of her as she was older than Billy and usually away at college on an athletic scholarship for cheerleading. She still had everything she owned in her room when she came to visit. Billy was always a great swimmer and good enough to compete in the state championships. Billy, like his father, was about 6'2 which gave him a huge advantage in swimming. Being on the swim team we always made it a point to keep our bodies shaved smooth like all swimmers do. Billy had won state in a few of his competitions and was heavily recruited by many elite colleges. The week after we had just graduated high school Billy was going to look at a few colleges that were offering him a full-ride athletic scholarship. I told Billy that I would swing by Saturday evening to say my goodbyes and watch some games before he left for the next two weeks. When I arrived at his house Saturday evening his father answered the door. He informed me that the first college had changed Billy's travel plans and picked him up much earlier than anticipated. He invited me in and told me all the usual food we ate had been delivered and he couldn't eat all of it by himself. Also, he was looking forward to watching the game, and watching it alone would be a boring way to watch it. I agreed since all of us watching the game was the plan anyway. We always ate at the kitchen counter. It was easy to move and didn't require sitting. As I entered the kitchen everything was familiar. There were chips and salsa, wings drenched in sauces, queso, pizza, etc. It was always a production his father put on. I think he enjoyed hosting. I don't think he'd admit that he didn't like to be alone either. The game started amazingly. Both teams were playing well. I had loaded up my plate with everything there was to offer. I had chips, salsa, and wings drenched in sauce piled on my plate. During one particular play, the refs completely blew a call. I was so mad I slammed my fist on the counter to protest. At least that is what I intended to do. Instead of hitting the counter, I hit the side of my plate and all of my food went flying into my face and all over my clothes. I was wearing shorts and a loose white T-shirt. There was food everywhere. Without missing a beat Billy's dad, Alec, told me to strip off my clothes and go take a shower in Tiffany's room and that he'd lay out some clothes for me and start the laundry so my clothes wouldn't stain. Tiffany had the master bedroom so she could have privacy. As I was showering I noticed all the soaps and shampoos were scented just for women. I thought "Oh well, no one is going to smell me." So I used them as it wasn't a big deal. I stepped out of the shower smelling of lavender and used one of the big pink fluffy towels there. I exited the bathroom and my jaw hit the floor when I saw what was laid out for me to wear. A pair of hot pink satin bikini panties, a pink mini floral halter top, and a low-rise black mini skirt. I stood there completely befuddled at my situation. I had never worn women's clothing and to be wearing Tiffany's clothes seemed taboo. Furthermore, I was kind of getting turned on by this situation. Not knowing what to do I yelled into the kitchen that the only clothes in there were Tiffany's. Alec yelled back that I wouldn't be able to wear his or Billy's clothes because they were too big and that would be the only thing that fit. Also, my clothes still had over an hour to wash and dry. Furthermore, it was just us two at the house and no one would be coming here anytime soon and halftime was almost over. Those were all valid points that he presented. I went back to the bed where the clothes were laid out and slowly picked up the satin panties. I couldn't believe how good they felt in my hand. I hated to admit that I loved the color and the detail in them. They were hot pink with black lace trim and a cute tiny pink bow in the front. I slipped one foot through then the other. I couldn't believe how great it felt once they hit my cock. I was rock hard in these pretty pink panties and the pre cum oozing already was proof that my body liked this. As I was standing in front of the mirror I heard Alec yell from the front room "Hurry up, the games are about to start." So, I quickly put the pink floral halter top on followed by the low-rise black mini skirt. I did another double-take in the mirror. The halter top didn't hide my abs and the skirt showed off my legs and butt. I couldn't believe that this was me. I yelled down the hall to not laugh and that I was coming out. He promised so I stepped out and started heading down the hall. The next thing I saw was a big flash of light, then another. Multiple flashes were going off. Then it occurred to me that he was taking pictures of me all dressed up in this very provocative outfit. I yelled at him to stop and ran down the hall back into the bedroom. Earlier I had taken my keys, wallet, and cell phone with me into the bedroom to shower so I wouldn't lose them. The next thing I hear is my text message going off. It was a picture of me all dressed up in Tiffany's clothes. There was no mistaking it was me and no good way to explain to her what happened. The message said to come back and watch the game with him dressed like that or these would be sent to Tiffany, Billy, my parents, and even to my boss! Alec was not the type to bluff so I knew he was serious. I slowly made my way back out and down the hallway to where Alec was. Alec told me I should never keep him waiting and as punishment, I needed to go put on one of Tiffany's Halloween wigs and put on lipstick and a bra as well. I knew what the consequences would be if I didn't comply so I slowly made my way back to her room and opened her dressers. I picked the matching bra that went with the panties, the bright pink lipstick, and a blonde wig she had worn on Halloween. I had never put on lipstick before. By the time I was done, I looked like a cheap street whore who used way too much lipstick. The wig was a little past shoulder length and made my facial features look even more feminine. I didn't know that was even possible. He told me to come out and be quick. I knew not to keep him waiting. When I entered the room there were even more pictures taken of me. He informed me that I was going to model this outfit for him. He had me take off the top and show him the bra I was wearing. More pictures were being snapped as well as videos. Then he had me lift the skirt to show the matching panties and bra. I obediently complied, forgetting about my aroused state. He took one picture of me wearing the blonde shoulder-length wig, hot pink bra, black mini skirt, and my little cock oozing pre-cum into the silky panties. The pre-cum changed the color of the panties and seeing the large wet spot in the panties was simply undeniable. He took a few pictures of me like that before I figured out what he was doing. He referred to those last pictures as "the money shot." I knew deep down that he now owned me. No matter what I did or said he had proof that I was dressed like a little sissy. Worse still that I loved being dressed like his little sissy. He informed me that he would treat me right if I was obedient. However, if I wasn't he would punish and spank me. Both options sounded like fun. What was I thinking? Fun? I'd never been with a guy before or even a girl for that matter. I'd never been spanked either but was pretty keen on the idea. I found myself willing to do whatever this dominant man wanted me to do. It was hypnotic how he would instruct me and I would just obey. I could feel his gaze scan over my body looking at my smooth skin. There was a palpable tension in the room. Alec finally broke the silence and told me I looked cute and sexy in the lingerie. Why was being called cute and sexy making me feel so aroused, docile, and submissive? Is this what I have always wanted? To be called cute, to be seen for once, and not be invisible. Deep down I knew he was telling the truth and I loved it. He slowly made his way over to me and took my bra straps down. Towering over me he slipped his warm hand into my bra. His palm cupped my A-cup breast. His thumb and forefinger start circling my erect pink nipples. Without warning he gave my nipple a tight pinch and twist. I let out an involuntary moan of pleasure. The other hand had slowly made its way down my side and to the panties. I felt his hand tug the waistband with his finger. He let the waistband go and it made an audible loud "snap" against my smooth skin. My little penis was rock hard. I had never been treated like this before and I loved every minute of it. Without a word, he grabbed my hand and let me into the bedroom. He had me face him then he gently yet firmly kissed me. As we kissed I found myself opening my mouth. His tongue expertly maneuvered in my mouth. As we kissed I felt his hands wrap around my tiny waist as if he was measuring me. I felt his hands on my shoulders and gently pushing me down to my knees. My heart stopped when he motioned me down because instinctively I knew this was where I belonged. As I was kneeling he had already taken his shirt off. Then he unbuckled his belt and let his pants hit the floor. Without thinking I reached out and slowly slid his underwear down. When I was tugging them down his huge cock sprung out and hit me in the face. I gasped at the size and that I was just smacked in the face with this man's hard cock. Suddenly I felt his large hand reach down and lift my chin. His hand pulled me closer to his cock and my lips, heavy with lipstick, grazed against it. Realizing my lips had just connected with this massive cock I slowly opened my mouth and stuck my tongue out and flicked it. Then I slowly started kissing every part of this amazing cock. His moans let me know that I was doing a job. I felt his hand grab the back of my head and he instructed me to open up. I opened my mouth and stuck my tongue out. Alec placed his erect cock on my lips and my tongue supported the base. I could taste him. It wasn't unpleasant and I knew I wanted more. He pushed into my mouth slowly and gently at first. Soon enough he started increasing the tempo with more vigor. My mouth and jaw were stretched as far as they could be. His hot cock hit deeper into my mouth and throat. All the while my little dick was bouncing up and down in the cute panties I was still wearing. I loved that I was giving this man so much pleasure. I could tell that he was getting close as he firmly grabbed my head with both hands. His hot warm cock still pounding my mouth wanting release so badly. Suddenly he pulled my head forward and drove his shaft deeper into my mouth. With a final thrust, he pushed as far down my throat as possible and unloaded down my throat making me his little sissy bitch. As he pulled his throbbing shaft out of my mouth it made a loud, audible pop. Waves of semen were in my mouth and dripping down my chin. All of a sudden I heard a click sound again. He had snapped a few pictures and had been taking videos of me while I was sucking him off. At that point, I had lost all sense of reality and knew that I now existed for this man's pleasure. Whatever he wanted and whenever he wanted I knew I had to comply. In all honesty, I wanted to comply. It felt amazing to feel lusted after. I loved how it felt to know that I had made this man cum, hard. Wearing and swallowing all his cum I knew that I would be seeing him again soon. I still hadn't cum myself but like an alpha he made me keep licking and sucking until I had gotten every drop out of his cock and balls. Alec told me how amazing that was and that I did a great job. By this time my clothes had dried. Alec made me wear the bra and panties as I dressed in my normal clothes. He didn't let me clean up either. He told me to be back tomorrow and I'd better be wearing those same bra and panties because sissies don't wear male underwear. He made it very clear if I didn't there would be consequences. I hadn't even left yet and I was already looking forward to what tomorrow would bring. If you liked this story and would like to hear more please email me sissychanel9@gmail.com