Disclaimer: SissyAndi stories contain sexually explicit descriptions of consensual and Non-Consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. The characters in these stories are fictional. All Stories are the property of the Author. Any feedback would be greatly appreciated. Thanks.
Authors Note: The following story is part of the ongoing saga of Andi, a 15 year old, cross dresser who is 5'9" 130 pounds, long blonde hair and blues eyes.
While it is my hope that each chapter will be entertaining as a stand alone story, I suggest that all new readers go back and read the "Andy And The Team" series, as well as previous entries in the Andi's Adventures Series. They contains a lot of back ground information that will help explain each story.
Andi's Adventures - Part 22
I had recovered from the Halloween party at the frat house. It was Monday afternoon when I got a call from Marcus, who I thought was my boyfriend. he had been at the beach all weekend and he was calling to ask if I wanted to come over. He had something he wanted to talk to me about.
On my way over to his house I was hoping we would do more than talk. I wore a simple black dress that came just to below my knee. I was wearing a gray bra and panties set and a pair of two inch flats. I know Marcus liked my hair back in a pony tail but I was wearing it down today. I was wearing my favorite shade of red lipstick.
In the past, if I did not have a ride, Marcus would always pick me up. Today he did not offer to come and get me and I ended up taking the bus. I hated taking public transportation, the bus was crowded and I had to stand and try to keep my balance while holding onto an overhead bar.
There was this older overweight white guy standing behind me. He took every opportunity to rub up against me. At one point I was wedge between him and another passenger and I could feel his hard cock pressed against my butt.
I felt his hot breath on the back of my neck and tried to move up but was unable to. I felt something as he reached between us trying to adjust his hard cock. He also took the chance to squeeze my ass making me jump.
Finally it was my stop and I had squeeze through the crowd to get off the bus. I was glad to be free as I walked the short distant to Marcus's house. I found him in the garage working on his motorcycle. He was wearing a pair of lose fitting shorts and a thin T-shirt. His 6' tall muscular frame always made my mouth water and just thinking about his 10 and 1/2 inch cock always made my mouth water.
When he seen me he stopped what he was doing. He took me into his arms and kissed my forehead. I tried to kiss his lips but he pulled away and told me to come inside so we could talk. I had a real bad feeling in the pit of my stomach.
I followed him into the house and he asked if I wanted anything to drink. I told him no thanks and waited on the couch while Marcus went and got himself a cold beer. Instead of sitting beside me on the couch, Marcus sat down in the recliner.
I wanted to ask him what was going on so bad but made myself wait until Marcus said something first. He looked me up and down as he took big swallows of his beer. Then he just cam out with it. He said he thought it was time to end things between us.
I was shocked because this came out of nowhere. I immediately started crying. Asking him why. He told me it was nothing I did or did not do. He just thought it was time for a change. He said he enjoyed what we had but he had decided to go back with his ex-wife.
I beg him not to break up with me. I mean I literally got on my knees in front of him and begged him not to end things. He said he had made up his mind and that was that. At this point I was desperate. While I was on my knees I reached out and cupped his cock through his shorts.
He pushed my hand away and told me to stop. I again begged him not to do this as I tried to free his cock from his shorts. He did not fight me but just watched as I tried to work his shorts down his legs. He stopped me again and told me that maybe I should leave. I was mad and I was heart broken.
I don't know why but I looked at him pleadingly and asked him if I could suck him just one more time. It was humiliating having to beg him to let me suck him but I wanted and needed it one last time. I was also hoping that maybe If UI did a good enough job I might could change his mind.
He finally shook his head yes and raised his hips allowing me to slide his shorts off exposing his semi hard cock. I took the shaft in my hand and started licking the head. I wanted to give the best blow job ever, I wanted Marcus to realize what he was giving up.
I took my time and bathe his balls with my tongue. I lick the soft sensitive place between his balls and his ass. I was working my hand up and down as I smothered his thighs with soft kisses and long licks. I took the head into my mouth and sucked it hard. By now he was rock hard and I wanted to show him I could take it all. I started working my mouth up and down slowly taking more and more into my mouth each time.
After a long time and a good deal of effort I felt his coarse pubic hair tickling my nose. I had taken the entire length of his cock into my mouth and throat. I pulled back letting all but the head out of my lips then I would plunge my head back down engulfing his cock again.
I was fighting my gag reflex each time I went down on his cock but I was determined to make him have an incredible orgasm. I squeezed and fondled his balls as I sucked his cock. Marcus was breathing hard and occasionally moaning. When his cock throbbed and grew even bigger I knew he was about to cum.
I pulled back a little so I could still breath and swallow at the same time. When Marcus came he flooded my mouth with a sea of cum. I still swallowed most of it but some did drip form the corner of my lips and run down my chin. When the flow of cum subsided I pulled my mouth off of Marcus's cock.
I started licking around the base and his crotch licking up what cum was left. Marcus pushed me away. I again begged him to please do not do this. He said it was time for me to leave. He ordered me To leave now. I was stumbling as i ran from his house with tears flowing down my face.
I got on the bus and seen everyone staring at me. I was crying, my mascara was running and I realized when I got home I had spots of dried cum on my face. When I got to the house I went looking for Mom but she was out with her girlfriend so I went to my room and cried myself to sleep. ______________________________________________________________________________
I cried for a week, I would not even get out of bed in the morning. Mom called Ian, my private teacher, and told him I was sick and needed to be out a few days. My mom seen the miserable shape I was in and tried to console me. My friend Jamie called me and tried to console me He told me he wanted to be there for me.
Finally my best friend Cindy came to visit me. Cindy is Asian, 5' 3" tall. Really slim, gorgeous eyes and short black hair. When she arrived she was wearing a short red skirt and a red tank top with spaghetti straps. She is also a girl like me, one born male but living the life of a female.
Cindy let me cry on her shoulder. After a long period of telling me it would be alright She decided to take another approach. She told me to get my lazy ass out of bed. Enough was enough it was time to try and put it behind me. She went into the bathroom and filled the tub with hot water. She added some scented bubble bath and came back to get me.
While she was in the bathroom I crawled back into bed and covered my head. When Cindy came back she acted pissed. She yanked the cover off of my bed. Then she took my arm and pulled me to my feet. I told her to leave me alone. She continued to guide me toward the tub.
Cindy kept talking to me the whole time, telling me it would get better but I had to at least make an effort. She even started unbuttoning my silk pajama top. She slide my top off my shoulders and then told me to take my pajama shorts off.
I finally showed some life when I slide them down and off. Cindy pushed me to the tub. I got in and let the warm water cover my body. Cindy sat on the edge of the tub, continued to talk to me, and watched me take my bath. When I had washed my body she offered to wash my hair.
It felt good to be pampered. I loved Cindy with all my heart. She seemed to know just what I needed. After I had soaked in the tub until the water was cold. I stood up and as I got out of the tub, I pulled Cindy close and hugged her tight getting her all wet. After the hug Cindy wrapped me in a big fluffy towel drying me off.
She led me back to the bed and set me on the edge, she sat down beside me and took me into her arms, hugged me close and told me everything would be ok. Then she kissed me lightly on the lips. Then she kissed me more passionately. As we kissed I felt her hand on my thigh caressing it.
Cindy broke the kiss and leaned her head down sucking my right nipple into her mouth. I let out a low moan as she went from one nipple to the other. She worked her hand up to my "clit" and starts squeezing it. After some time of this I become hard and Cindy pushed me onto my back. She bent down and starts kissing my clit and swirling her tongue around it.
Cindy took my small limp cock into her mouth and sucks it gently. As she sucked my clit she worked her hand under me and slowly starts working one, then two fingers in and out of my butt.
I was so depressed I had not even thought about sex and had not cum in almost a week. Cindy was good at what she was doing. She had my clit rock hard in not time.
Cindy was sucking my clit and fingering my butt and she had me moaning and shaking from the pleasure. before long my whole body tensed up and I went into spasms as I came so hard I momentarily passed out.
When I regained consciousness Cindy was laying beside of me holding me tightly in her arms kissing me again telling me everything will be alright. I drifted off to a blissful sleep feeling better than I had since Marcus dumped me. Sometime in the evening Cindy slipped out of bed without disturbing me. I found the note when I woke up, Cindy wrote that she loved me and I would be ok in time.
I had resumed my studies with Ian, I still did not feel like venturing out of the house though. Ian had talked his Aunt into letting us use the pool house for my tutoring. It was private and we were not disturbed by the maid, visitors or anyone else. he even had a desk set up like you would see in a real classroom.
Cindy would call every day to check on me and to encourage me to get out there and have fun. She kept telling me to find someone new, it did not have to be a serious relationship. If nothing else just find an anonymous cock and have incredible sex.
I did not know about finding someone new or anonymous, but I was missing the sex part of my life. That is when an idea formed in my head. Ian had not said anything about what happened Halloween weekend and he has not made advances to me, he had been strictly professional ever since.
I decided that was going to change today. I showed up at the pool house dressed in a sweater and jeans and we got to work. After about an hour or so Ian said we should take a break. I agreed.
Ian was 5' 11", has short brown hair, dark eyes, he was in decent shape, not muscular but not flabby. He also had a beard that made him look older, like a college professor. I figured he was a good choice to get back in action.
I grabbed my book bag and excused myself. I went to the bathroom to get ready for Ian's surprise. I stripped off my sweater and jeans. Underneath I was wearing a plain withe cotton bra and basic white cotton panties.
I laid out my new outfit and started getting dressed. First I slipped on a thin white almost see through blouse. I left the top three buttons undone and rolled up the sleeves.
Next came a red and black plaid skirt that was so short that if I reached up or bent over I would be exposing my panties. I reached in my bag and got out the white knee socks. Then I slipped my black patent leather shoes back onto my feet.
I took some rubber bands and put my hair up into pigtails. I made sure to put on a heavy coat of dark red lipstick. When I looked in the mirror, staring back at me was a slut with the classic naughty catholic school girl look.
I peeked out of the bathroom door and seen that Ian had his back turned to me so I tiptoed back into the room. In my best little girl voice I said "Mr. Rhodes can you give me some special help after class?"
He spun around and saw me standing there. His eyes got big and his mouth hung open, but I have to hand it to him, he recovered quickly.
"Well Ms. Andi I think I can help you out, you seem to need a lot of direction."
I smiled at him and he took me into his arms and started kissing me, I felt him exploring my mouth with his tongue so I started sucking on it. I felt hi right hand squeezing my breasts through my clothes.
Ian broke the kiss and told me I had been a very bad girl. I giggled but stopped suddenly when he spun me around and bent me over his desk. He had one hand on the small of my back pinning me down. The other hand was pushing up my short skirt and rubbing my ass. He pulled my panties down to my knees.
I let out a yelp when the first blow hit my ass. he had an old wooden ruler that he was spanking me with. He smacked my ass with that ruler over and over as he kept telling me what a bad, bad girl I had been. The spanking stopped when Ian leaned in and started kissing and licking my butt. I felt him spread my ass cheeks and push his tongue into my butt. He licked deep then started swirling his tongue around rimming me.
it felt incredible and I wiggled my ass. When Ian removed his tongue I looked back over my shoulder and seen that he was undressing. I started to stand up and he ordered me not to move. When he was completely undressed, Ian told me to turn around. He had sat in his chair and was stroking his cock.
Ian said "You are such a naughty cum slut, get on your knees and show me just how much you loved cock."
I got on my knees. before I could do anything, Ian reached out and force my mouth down onto his hard cock. He was not gentle and I gagged. That did not even cause him to slow down. Ian had one hand on each side of my head and was forcing my lips up and down his cock.
Ian must have been really turned on by using my mouth because he came hard without warning. I tried to swallow as much as I could before Ian finished cumming, he pulled out letting two or three strands of cum hit me in the face. Ian let go of my head and leaned back in his chair. I went to wipe his cum from my face but he stopped me. He told me to start over and give him a proper blow job.
I took his cock in my hand and started licking his cock. I licked and sucked on his balls. I went back to sucking his cock. I would work my mouth up and down taking his entire length in my mouth. Before I could get him off again Ian pushed me away. He stood up and turned around.
He reached back and spread his ass cheeks. Ok slut eat my ass like I did yours. I was reluctant but I pushed my tongue into his ass. He ordered me to lick deeper. I stuck my tongue deep into his ass. It was a musky, tangy taste, not as bad as I thought it would be.
I started to tongue fuck his ass, swirling my tongue around and round rimming his ass. Ian kept pushing his butt back to me trying to feel my tongue even deeper in ass. Ian turned around and pulled me up by the pigtails. He pushed me back onto the desk and grabbed me by the thighs lifting my legs into the air.
Ian lined his cock up with my ass and drove his hard cock deep into me. Good thing he had licked my ass and I had sucked his cock earlier or he would have forced his cock into me without lube. It hurt enough as it was. Well it hurt at first, soon it was feeling so good.
Ian let go of my legs and reached down ripping open my blouse. He pushed up my bra and started slapping my small breasts as he fucked me. He repeatedly slapped my breasts then started pinching my nipples. Soon he was slamming his cock into my ass and twisting my nipples.
I felt an intense pleasure build inside of me and I could not stop it if I had wanted to. I came and I came hard. Ian pumped his hard cock in and out of me and continued to abuse my nipples.
He drove his cock deep and held it there, He leaned down and started sucking my right nipple. Then he switched and sucked on my left nipple.
He bite down on the nipple sending a searing pain through my left breast. I was hard again. Ian reached between us and started stroking my small cock.
Since I had started on hormone therapy I had not been able to cum more than once, even when I was with Marcus. I had already cum once and Ian had me on the verge of a second orgasm. Ian squeezed the head milking the pre cum from my small cock. He took my pre cum and rubbed it onto my nipples then he licked my nipples clean.
When my second orgasm hit me I got very light headed. Ian caught what little cum came out and pushed his fingers into my mouth where I sucked his fingers hungrily.
Ian resumed fucking me. He rammed his cock into me hard, fast and rough. He had already made me cum twice, now he was only interested in his own pleasure. He was sweating and breathing hard. I felt Ian drive his cock deep, his cock started to throb and there was an explosion in my ass as he filled me with hot cum. He collapse on top of me and gave me a deep hungry kiss.
We were both covered in sweat and cum. As Ian rolled off of me he laughed, kissed me again and said that what I did was worth a B at least. I playfully slapped him on the arm and said I thought I deserved an A. We both started having giggling fits as we continued to kiss. Ian got dressed and I went back to the bathroom to clean up.
My blouse was torn and several buttons was missing and my little red and plaid skirt was ruined as it was covered in cum from both of us. Oh well clothes can be replaced and it was definitely worth it. I was already starting to forget about Marcus.
More to come, especially if I continue to get positive feedback.