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. She has a set of perky 32B size Breasts.
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 24
I awake in a strange bed, the sun is just starting to rise, the warm rays filtering through the window. I look over and see a very handsome man sleeping beside me, snoring lightly.
I am still wearing my black panties, garter belt and stockings. My little black dress was no where in sight but then I remembered taking it off in the living room.
Memories of the previous night come flooding back as I run my hand across his muscular chest and down his nude body. _______________________________________________________________________
It was Friday night and I agreed to go with Jamie to a local teen club. Jamie's cousin was the head of security for the club so we got in for free. I tried to talk Jamie into going to the club as a female but he said there was no way he could do that because no one in his family besides his Mom knew that he liked to cross dress on occasion. If he went dressed up, his cousin would recognize him and his secret would be exposed.
So I went as Jamie's date. When we got to the club Jamie introduced me to his cousin Tim. Tim was a senior in college and worked at the club on the weekend. While Jamie was a good looking guy who made a really sexy girl, Tim was all MAN. He must work out constantly to look like that. He was 6'3", Short Sandy blonde hair, gorgeous blue eyes.
Tim was wearing tight jeans and a really tight black T-shirt with the word security across his chest. All the young girls in the club were drooling over Tim. I know he made my mouth water. I could not help stealing glances at his crotch wondering how big his cock was.
Jamie and I found a table and order some soft drinks. Most of the boys in the club were dressed casually while the girls tried to look sexy in dresses and short skirts. The music was loud and upbeat. Jamie and I share a couple of dances. One was a slow song and I rested my head on his chest and felt his hands on my back, then my butt.
When we went back to our table, I noticed Jamie looking at this really cute redhead. I nudged him and told him he should ask her to dance. He smiled and said but I was his date. I told him it was ok I didn't mind.
I watched as Jamie lead her out on the floor. Jamie was not a bad dancer but the red head was pretty good. They made a cute couple.
I was sitting alone sipping my drink when Tim came by to see how we were doing, I told him that it looked like Jamie was doing great and pointed to the dance floor where the red head was grinding her hot young body against Jamie as they danced.
That was when Tim told me he did not know what Jamie was thinking, he came here with the hottest girl in the club and he left me sitting here to dance with someone else. I told Tim thank you but that Jamie and I were just really good friends.
I danced with a few different guys through out the night, no one I really liked enough to dance with a second time. Jamie and the redhead came back to our table and he introduced her as Sharon. She pulled Jamie closer to her when she seen me.
We sat and try to chat over the music but it was a lost cause so we just watched the crowd. Since it was a teen club it had to close by 10:30. At about 10:15 Sharon who turned out to be 17 said she had to take her friends home. Jamie and Sharon traded a deep wet hot kiss good night and Sharon told him to call her.
Tim came by again and asked Jamie how we were getting home and we told him on the bus. Tim told us if we wanted to wait he could drive us home. Since I really hated riding the bus we decided to take him up on his offer. Jamie said it was too hot in the club and asked him if we could wait in his car.
Tim handed Jamie his keys and told him the car was parked around back behind the club. It was dark and kind of creepy back there. Tim had a new big SUV. Jamie unlocked the doors and he crawled into the drivers seat. I got into the passenger seat.
Jamie asked me if I had fun, and I told him yea, but apparently not as much fun then he did. He laughed and said he did enjoy dancing with Sharon even if she did leave him with a painful hard on. We both laughed.
That is when he looked at me with that crooked smile of his, "Ah Andi, could you help me with that. please?"
"Oh so you leave me sitting so you can be with another girl and when she will not put out you come to me for help."
He started to apologize until he realized I was just teasing him. I reached over and rubbed the bulge in his jeans. Jamie moaned and reached down and unzipped his pants and fished out his hard cock.
I started working my hand up and down the shaft and heard Jamie let out another low moan. Jamie reached behind my head and pulled it down toward his cock. I resisted but Jamie continued to force my mouth toward his erection.
I heard him say "Come on Andi, suck it for me, I need to get off really bad."
I opened my mouth and took the head between my lips. Jamie was still applying pressure, forcing more of him cock into my mouth. I felt the head hit the back of my throat and I knew I had the entire length in my mouth.
Jamie eased up and let me pull back some then he forced my head back down. Sharon must have really turned Jamie on because I had never seen him this aggressive.
I finally managed to pull my mouth off of Jamie's cock and I gave him an annoyed look. He looked amused. I just sighed and went back to sucking the head of his cock. I squeezed his balls while I started working my mouth up and down the shaft again.
Jamie had decided to let me work at my pace and not his. I knew I needed to hurry though because Tim would be coming out soon, so I started to work my magic. I would vary the speed at which I sucked his cock. I would bob my head up and down quickly, then I would slowly and lovingly work my lips up and down the length of his cock.
I felt the head of Jamie's cock enlarge and I new from experience that he was about to cum. I pulled back and sucked hard on the head. Jamie thrust his hips forward and started cumming in my mouth. I swallowed quickly and was proud of myself for not losing a drop.
I was wiping my lips off with some tissues and Jamie was zipping up when we seen Tim coming around the corner of the club. _____________________________________________________________________
On the drive to Jamie's house I noticed Tim kept checking out my legs. I turned to talk to Jamie in the backseat and I let the hem of my dress slide up a little showing off more of my legs and the top of my stockings.
I felt the car swerve and Tim's eye went back to the road. I just assumed that Tim would drop us both off at Jamie's house and I would take the bus home but Tim said, "Now what kind of gentleman would I be if I left a sweet young thing like you to fend off perverts that ride the bus late at night."
After we left Jamie at his place I scooted over close to Tim and gave him a kiss on the cheek. I let my hand linger on his arm as I thanked him for giving me a ride home.
Tim said it was still early and it always took him a while to wind down after work. He asked me if I had a curfew and did I have to go straight home. I told him that my Mom was away on a trip with her girlfriend and that I was suppose to call her and tell her I made it home ok. With that I pulled my cell phone out and dialed Mom.
I was a little surprised when Jillian, my Mom's boss and lover, answered the phone. Jillian told me that Mom was a little tied up at the moment and laughed. I heard mom moan in the background.
I asked Jillian to tell Mom I made it home ok and I would talk to her tomorrow. Jillian told me she would let my her know and the phone went dead.
"There, I am covered for the night, so to answer your question, no I don't have to go home right away."
Tim smiled again, "lets go back to my place and hang out."
"Ah Tim, we need to talk about something before we go any farther."
Tim looked at me and seen the serious look on my face so he pulled into a deserted lot and parked. He turned the Car off and turned to give me his full attention.
I did not really know how to start bet decided that honesty was best. "Tim I feel an attraction between us but I do not want to mislead you. Ah, I am not what you think."
Tim keep his eyes on me and asked "What exactly does that mean?"
"Tim I am not a girl." I seen the look of confusion on his face. "I mean not technically. I was born a boy but I never felt right as Andrew. My Mom and I talked it over and we decided that I was meant to be a girl. Just over a year ago She took me to the doctor and he started me on hormones."
To his credit Time never looked away. The he smiled. "There is a picture in Jamie's room of him and a blonde guy, I was going to ask you if it was your brother. That is you in the picture isn't it?"
I just nodded.
"I have to ask, have you had surgery yet or do you plan on having it in the future?"
"No Tim I have not had THE surgery yet and right now I am not really considering it, maybe in the future. I have talked to my Mom about having breasts implants someday."
Tim surprised me, "Why? I think those perky little breasts of your are awesome. I would not change a thing."
That made me smile and I relaxed a little.
"Why thank you. So I take it you are not freaked out about me?" I asked.
He said no and that he still thought I was the hottest girl at the club tonight.
I thanked him again and took a chance and gave him another kiss on the cheek. Tim turned his head and lightly kissed me on the lips. before I knew it I felt Tim slip his tongue passed my lips as he started exploring my mouth.
We made out for several minutes until Tim broke the kiss. "So do you still want to hang out at my place?"
I kissed him again and said I would love to.
Tim had a really nice apartment, he had a room mate but Tim said he worked late and they rarely seen each other.
Tim told me to have a seat as he went to and got us something to drink. When he came back he handed me a glass of wine.
He excused himself and said he was going to change clothes and would be right back. While Tim was gone I slipped off my bra and put it in my purse. When Tim came back he had on a lose fitting pair of shorts. I loved the way his muscular legs looked.
Tim sat beside me and I snuggled up close to him, I rested my head on his shoulder as we talked. Tim tilted my head up toward him and started kissing em again. The kiss became very passionate and I felt his hand on my right breast.
He started pinching my nipple through the thin material of my dress. I was moaning into his mouth as we kissed. Tim reached behind me and untied the top of my dress, sliding it down exposing my breasts.
Tim broke our kiss then kissed my lips lightly. He then kissed my cheek, my neck, he even nibbled on my ear. I glanced down and seen the impressive bulge in Tim's shorts.
I moved my hand to his crotch and touched it lightly, that made Tim moan. I started rubbing his cock through his shorts as he started kissing, licking, sucking and even biting on my sensitive nipples.
Now it was my turn to moan, I threw my head back and closed my eyes. I was loving the attention Tim was paying to my breasts and he sent shivers through my body when I felt his hand starting to caress my thigh.
I stopped Tim's hand and pushed his mouth away from my nipple. I stood up and let my dress fall to the floor. I stepped out of it and laid it across the back of the couch. Then i stepped between Tim's spread legs and leaned down. I blew my hot breath onto his cock and watched it jump through his shorts.
"Baby take off your shorts, I want to see that beautiful cock." I cooed.
Tim quickly lifted his hips and slide his shorts off. OH MY GOD, I thought to myself. It was only 8 inches long but big around. It had a big mushroom head and a red vein that ran underneath the shaft. He squeezed the shaft and i could see the whole cock throb.
I could not resist, I leaned down and kissed the head as he instinctively raised his hips trying to force the head into my mouth. I asked Tim if we could go to his bedroom just in case his room mate came home.
Tim stripped off his T-shirt as he lead me into the bedroom. Before I could react he came up behind me and took me into his arms. I was facing away from Tim as he started kissing my neck again. Tim reached around and started mauling my breasts again as I felt him start grinding his cock against my ass.
Tim was pushing me to the bed the whole time. He pushed me face down onto the bed. I felt him get on the bed behind me. I expected to feel his cock head against my ass but was caught off guard when he pulled my panties aside and I felt Tim start kissing my ass cheeks.
He spread my cheeks and I felt his wet warm tongue start to dart in and out of my ass. It felt incredible and I caught myself pushing my ass back trying to get him to push his tongue deeper into me.
Tim started swirling his tongue inside my butt. I was grinding my little clit against the bed and felt an orgasm starting to build. I was disappointed when Tim quite tongue fucking my ass. That is when I felt his cock pressing against my butt. OH god the head was big and it was stretching out my ass.
Tim let out a low growl as the head of his cock popped into me. He slowly pushed forward. Tim was taking his time enjoying the feel of his cock sliding into me. Soon I felt Tim's pubic hair tickling my butt and knew he was completely in me.
He stayed there letting me get use to having his cock in my ass. When he felt me push back against him he started slowly pulling back. He went slow at first and it was driving me crazy. Suddenly Tim rammed his cock into me and started picking up the pace. That sent me over the edge and I emptied my cum into my panties.
By now Tim was working at a steady but rapid pace. He was fucking me deep and hard and I was loving every second of it, he really knew what he was doing.
He would fuck my ass until he was on the verge of cumming, then he would stop and let his cock settle down, then fuck me hard again. He was driving me crazy. The last time he stopped, trying to prolong it, I decided to take things under my control and I started pushing back hard against his cock. I was squeezing my ass together trying to milk Tim's cock.
I knew he could not hold out forever and Tim growled and shoved the entire length of his cock deep into my ass. I felt blast after blast of hot cum shooting into me and when Tim was done he collapsed on top of me.
We laid there for a long time, each of us trying to regain our strength. Finally Tim rolled off of me and went to the bathroom, I rolled over onto my back and was dozing when Tim climbed back onto the bed.
Before I knew it Tim had put his hands under my legs and lifted them into the air. He was already hard again and he had no trouble slipping his cock back into my already used ass. This time he was not worried about making it last. He started fucking me hard, deep and fast.
Tim leaned down and kissed me. He pointed my legs straight up into the air. As Tim worked his cock in and out of me I felt him run his hands up and down the back of my stocking covered legs.
I heard Tim moan "Oh god I am gonna cum again!!" Instead of cumming in my ass a second time he pulled out and shot his second load all over my tummy and chest. I lay there panting trying to regain my breath as Tim laid down beside me. I had to smile because he looked exhausted.
As Tim got sleepy and started fading in and out I slipped from the bed and went to the bathroom and cleaned up. When i returned and climbed back into bed, Tim put his arm around me and pulled me close to him. _______________________________________________________________________
Feeling Tim's hard cock throbbing in my hand brings me back to the present. He must be having a naughty dream because as I grasp his cock it is already rock hard. I slowly work my hand up and down and I heard him moan as I squeeze the head.
I could not resist, I leaned down and kissed and licked the tip. That brought a groan from Tim. It dawned on me that I did not get a chance to suck Tim's cock at all last night and I had an overwhelming urge to deep throat all 8 inches of it right now.
I heard Tim mumble, "Oh hell" as I felt the head of his cock hit the back of my mouth.
As he started running his fingers through my hair, I knew Tim had come wide awake. "Damn I thought it was just a wild dream, but I guess last night really happened."
I just smiled up at him and continued sucking his cock. I squeezed his balls and was milking his cock with my lips. Tim must have recovered from last night because before long I was rewarded with a delicious load of cum.
Without thinking I raised up and gave Tim a deep kiss knowing he was tasting his own cum on my lips. He did not seem to mind as we made out while Tim squeezed and groped my ass.
Tim pushed a finger into my ass which caused me to grind my panty covered crotch into his cock. Tim was a wild one as I felt his cock start to get hard again. I sit up straddling Tim's waist.
I wiggled my butt on Tim's cock as he reached up and was squeezing my breasts and pinching my nipples. I got up onto my knees and reached back spreading my ass. I lowered my still sore ass down onto Tim's cock. It slide into me easily.
I started raising and lowering myself up and down his hard cock. I was going slowly and I guess Tim got impatient. I felt his hands around my waist and he started lifting me up and slamming me down onto his cock. Oh wow, in this position Tim was able to get his cock even deeper into my ass.
After twenty five minutes my knees and my ass was starting to hurt. Tim groaned and slammed me down onto his cock one more time and he came again time in my ass. I really liked this guys stamina. I collapsed onto his chest again and fell asleep.
It was almost noon when Tim woke me. He told me to get dressed and he would take me home. i got out of bed and started looking for my dress and remembered it was in the living room.
I walked out wearing only panties, garter belt and stockings to come face to face with Tim's room mate. Oh my, He was a tall, broad chested, well built black man. The room mate stood there with his mouth hanging open as I grabbed my dress and slipped it over my head.
Tim thought both of our reactions were hilarious. When he quit laughing, Tim introduced me to Nathan his room mate. Nathan turned to Tim and jokingly said "She is gorgeous, You are a God."
I found my purse and heels and asked Tim if he was ready to take me home.
Tim was quiet on the drive to my house. when he pulled into the driveway he commented on what a great house. I told him that My mother worked for the owner and she allowed us to live there.
Tim leaned over and gave me a kiss, then he told me, "Andi I had an incredible time, but I don't want you to think I was just after sex. I want to get to know you better, I was wondering if you would go out with me on a real date?"
"Oh Tim I would like that, I think it would be fun", I dug in my purse and scribbled my cell phone number onto a card. "Call me any time."
Then I kissed Tim again. We made out for a while and then we both decided it was time for him to leave before we had sex right there in the driveway. ______________________________________________________________________
More to come, especially if I continue to get positive feedback.