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 18
My Mom and I had been living in what I have come to think of as Rhodes Manor for two weeks now. It was a large house with several bedrooms, a pool, a pool house and several acres of fenced in property.
I was living there with my Mom who had taken a job as a private nurse looking after the owners Mom. I think Mom may have been having a lesbian relationship with the owner, Ms. Rhodes. Mom has not come out and admitted it but at night she disappears for an hour or so almost every night and when she returns she has that look of a truly satisfied woman.
I had my own room with a queen size bed. The room was all feminine and elegant, There were no male clothes around and nothing that would remind me of my old life as Andy.
School had started and Jamie was busy getting use to public school without me. When Ms. Rhodes had hired my Mom she had offered a private tutor for me so I could be home schooled. My new teacher had some things to wrap up before he could start.
For now my days were free and I was laying out by the pool in my pale blue bikini working on my tan hoping to catch as many rays as I could before fall started. The old gardener and his young assistant were working on the flower beds. I knew they were checking me out I had my sunglasses on and I could watch the young guy without him knowing it.
Maria, the young Hispanic maid, brought the workers something to drink. Now my Spanish is not very good but even I could figure out that the workers were her Dad and brother.
I had rolled over onto my tummy to get some sun on my back and had dosed off. A voice woke me.
In accented English, Maria's brother said "Excuse me miss, Ms. Rhodes has always allowed me to cool off in the pool when we are done. Is it ok with you if I take a swim?"
I smiled "Of course its ok especially if Ms. Rhodes gave you her permission."
I rolled back onto my back and watched as he peeled off his dirty T-shirt and dove into the pool. Jose was cute, nice body, not overly muscular, very tan from all the work he does out doors.
He was 5' 10" and had straight brown hair and a mustache. I later found out he was 19.
I sat in my lawn chair and watched Jose do laps in the pool. When he started up the steps to exit the pool I grabbed a towel and took it to him.
As he dried himself off I asked him if he was indeed Maria's brother, he said yes and that the other guy were their Dad. He also told me that the dad had to run to the hardware store to get ready for the next landscaping job they had lined up and that it would be awhile before he returned.
I asked Jose if he would do me a favor, he smiled and said he always liked doing things for a pretty ladies. I handed him the bottle of suntan lotion and asked if her would rub some on to my back because there were places where I could not reach.
I laid back down on my lawn chair and he squirted some lotion on my back. I felt his strong hands start to rub lotion into my shoulders and the back of my neck. His hands moved down to message and coat my back.
When he reached the small of my back and my bikini bottoms I took a deep breath, what would he do next? He skipped over my butt and started at my ankles, working his way up.
His hands on my body felt so good, I was glad I was laying face down, my little clitty in not a problem when its soft, but right now it was hard and would have caused a small but embarrassing bulge in my bikini.
Jose was working his hands over my calves, then the back of my thighs. When I looked back over my shoulder at him, he had a bulge in his shorts, believe me his bulge was impressive, not embarrassing at all.
Finally I felt his hands messaging my ass. He started to rub down between my legs and under me. When I went to stop him he leaned down and said in a low voice, "don't worry, Maria told me all about you but I wanted to check for myself."
I rolled over in surprise and he took the opportunity to kiss me. He sat on the lounge chair beside mine and pulled me into his lap. As we kissed I wiggled my ass in his lap feeling how hard his cock was.
After several minutes of making out, and Jose rubbing my thighs, Jose reached down and unzipped his shorts.
"No Jose, we need to stop anyone could see us out here."
He took my hand and said for me to follow him. He lead me around to the back of the pool house. I looked around and while I was still nervous, I did not think anyone from the house could see us.
He kissed me again and was squeezing my ass through my bikini. He told me we had to hurry because his Dad was suppose to be back soon. He started pushing me to my knees.
The grass had just been cut and I was sure I would have grass stained knees, I should have brought a towel with us. I guess grass stains were better than rug burns.
Jose was leaning up against the wall of the pool house and he had pushed his shorts down showing me his hard cock, it looked to be 8 inches long and thick around and he was uncircumcised. When I touched it I could barely get my hand around it.
I was stroking it up and down, as I stared kissing from the base to the head. I went from kissing his cock to licking the length of it. because of work it had been a few days since I had been with Marcus. I had not had a load of cum in that time and I craved cum badly.
I started kissing and sucking his balls. Jose was moaning loudly I was worried as much about someone hearing us as I was about someone seeing us.
I took the head into my mouth and sucked on it slowly. He had his hand on the back of my head but he was just running his fingers through my long blonde hair. He was letting me work at my own pace.
I started bobbing my head up and down taking more and more of it into my mouth. Eventually I felt my chin brush his pubic hair and the head hit the back of my throat.
I was getting good at controlling my gag reflex. He held his cock deep into my mouth and I was sucking hard. He started working it in and out of my mouth again as I squeezed and messaged his balls.
I felt him tense up and his cock grow even bigger and then he shot his load into my needy mouth. When I was finished Jose helped me to my feet. As we came around the corner of the pool house Jose's Dad was waiting for him, he told him they needed to go to the next job.
I grabbed my towel and sun lotion and headed into the house. Maria met me at the door and said she thought she should warn me, Jose had a real jealous girlfriend and if she ever found out what I just did she would probably want to kick my ass.
I laugh and said I had a boyfriend that might not like what just happened either. ____________________________________________________________
Marcus was early when he picked me up for our date. He apologized and said that he needed to go by work before we went out.
I figured I would just wait in the truck while he took care of whatever it was he had to do but Marcus came around and opened the door for me, My skirt rode up my showing my stocking encased legs.
I was wearing a white silk polo top. A short black skirt, black garter belt, black stockings, a blue lace bra and matching blue lace panties. I was also wearing new 3 inch heels that I had bought over the weekend.
Marcus was wearing a pair of tight jeans and a T-shirt that fit his sculptured upper body.
Marcus led me to his office and I sat in a chair watching him do paper work. Workers kept coming in to ask him questions, Marcus was getting frustrated with them because I think most of the guys were just making up excuses to come by to get a look at me.
I caught Marcus looking at me, he smiled and said he could use a secretary and I would make a hot looking sexy one. He told me to get up and come to him.
I walked to him and he told me to get on my knees like a good secretary. I refused, I asked him what if someone came in.
"Come on Angel, its been a fantasy of mine to do a hot secretary in my office."
"I don't know, it still seems risky."
He stood up and took me into his strong arms and kissed me deep. He put his hands on my shoulder pushing me to my knees. I knew there was no use to resist because Marcus always got what he wanted.
I reached out and unzipped his jeans and slide them down, I started kissing and licking his huge cock through his silk boxers. Next I slide his boxers down to his knees. My right hand was stroking his 10 1/2 inch cock while I was sucking his balls like I knew he liked.
I was working my mouth up and down his cock when he pulled it from my mouth. He pulled me to my feet and spun me around pushing me face down across his desk.
"No Marcus not here please...."
Marcus had me pinned down with his right elbow as he pushed my skirt up to my waist with his left hand. He pulled my panties down.
He removed his elbow and I reached out to grip the edge of his desk with my hands bracing for what was to come as I felt him spread my ass cheeks. He inserted one finger and worked it in and out, then added a second finger.
I felt empty when Marcus removed his fingers. Soon though I felt the huge head of his cock press against my anal ring. I felt the pressure increase until the big head of his cock popped into my ass.
Marcus continued to push forward until he was completely in me. I felt so full, he had fucked me several times before I was able to take the entire length in me. I was happy as Marcus started working his cock in and out of me slowly.
When I left the house tonight I figured we would have sex, I had no idea that he would be fucking me in his office with me bent over his desk.
Marcus was playfully slapping my ass as he was slamming his cock into me. I was pushing my hips back to meet his thrusts allowing his cock to go deeper into me.
It had been a few days and it was dawning on me just how much I had become addicted to his cock. I was wiggling my ass and squeezing my butt cheeks around Marcus's cock.
He would pull back leaving just the head in me then he would ram his cock deep into me again and again. After 30 minutes Marcus was fucking me for all he was worth and I was in heaven and was on the verge of cumming.
My skirt was around my waist, my panties were around my ankles and Marcus was ramming his cock in and out of my ass with all the force he could muster.
It ended way to soon when I felt Marcus push his cock all the way into me and empty his huge load of cum sending me over the edge and I came also.
After he pulled out he sit back onto his office chair. I finally had the energy to stand up and I turned around and bent over and started licking his cock again.
It had started to go soft but with me licking it and eventually sucking on it, Marcus's cock was fully hard once again. I stepped out of my panties and took his cock in my hand.
I held it in place as I straddle Marcus's lap and slowly lowered my ass down on to Marcus's cock. As I was working my ass up and down on his cock I leaned into Marcus and kissed him passionately.
Our tongues were wrestling as we kissed, Marcus started pulling the hem of my top out from under my skirt. I broke the kiss and raised my arms to let him raise my shirt up and off.
Marcus started kissing neck as he reached behind me and undone my bra and sliding it down and off of my shoulders. He continued to kiss my neck then he kissed his way to my breasts.
His hands were on my waist lifting me up and down on his cock. His lips were on my nipples licking and sucking on them. I had my head thrown back moaning in pleasure.
Marcus bite down hard on my right nipple causing me to cum a second time. I must have been screaming as Marcus had to pull me to him and kiss me deep to quiet me down.
Marcus was grunting between kisses so I knew he was close to cumming again. I was riding his cock for all I was worth. Marcus slammed me down on his cock so hard I thought he was going to rupture my insides as he started cumming in me again.
I collapsed into Marcus's arms and was resting my head on his shoulder trying to get my breathing back under control. ___________________________________________________________
Marcus and I cleaned up and got dressed. We had worked up quite an appetite and both of us were starving. After we ate a great meal at a Chinese restaurant we went back to Marcus's house where we had sex a third and then a fourth time.
When Marcus dropped me off at home that night I was well fucked and extremely happy. As I was getting ready for bed I looked out my bedroom window and seen Mom and Ms. Rhodes in the pool.
They had the outside lights off but it was a full moon and there was enough light for me to see everything going on.
Mom who is 5'2" tall, 120 pounds, short red hair and dark green eyes looked hot in her floral bathing suit showing off her 34 B breasts.
Ms. Rhodes or Jillian is a very tall brunette, brown eyes, long shapely legs, and a bust that had to be 36 d at least. She was in great shape for a woman in her early 50's. and she had on a black bikini that left little to the imagination.
After swimming and playing in the water for a bit Jillian pulled herself up onto the edge of the pool. I watched as Mom swam to her. Mom positioned herself between her boss's legs and started kissing her thighs.
I watched as Mom slide the strip of clothed covering Jillian's crotch aside and starting licking her pussy. Jillian was leaning back on her elbows and you could see that she was enjoying what Mom was doing to her.
I was standing by my window and even though I had cum twice already that night, my little clit was hard again. I was in the middle of dressing for bed when I noticed what was going on at the pool. All I had on at the moment were black lace panties.
I realized I was rubbing my clit hard as I spied on my Mom and her lover. It felt good to rub my clit as I watched Jillian pushed Mom away and helped her out of the pool. Jillian quickly stripped Mom of her bikini and pushed her onto her back.
Jillian got out of her bikini and even in the moonlight I could see just what a great body Jillian had. Jillian swung her leg over Moms head and lowered her pussy to my Mothers mouth.
I was watching them lick each others pussy when without warning I came in my panties. My knees got weak I had to sit on the bed.
When I recovered I managed to stand and look out again. Mom and Jillian had left the pool area and were nowhere in sight. I went to the bathroom, washed out my panties and hung them up to dry.
As I was crawling in bed I heard Mom pass by my bedroom door. She was humming a country song and I knew from experience, Mom only hummed when she was very happy. ___________________________________________________________
More to come, especially if I continue to get positive feedback.