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 started hormone therapy and has a set of perky 32 B 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 25
It had been a cold and dreary winter. Every one seemed to be suffering from the winter blues. So Mom and her girlfriend decided we needed a break. They talked it over decided that we should take a vacation to some place warm.
Mom told me I could bring a friend, so I called Cindy and invited her along. She was reluctant but I finally talked her into it. Like it was hard to talk her into going somewhere warm and sunny when it got down into the low 20's in North Carolina at night.
So early on a Friday Morning we boarded a plane for Kingston, Jamaica. I figured we would be staying in a deluxe resort but to my surprise Jillian had rented a secluded beach front cottage.
The house had two bedrooms, Mom and Jillian took the master bedroom and Cindy and I took our luggage to the small bedroom at the back of the house, the only thing separating us from the beach and the ocean was a sliding glass door.
I wanted to hit the beach right away but Mom insisted we drive into town for lunch. We found a restaurant and ordered, The waiter seemed to be paying special attention to Me and Cindy. Mom and Jillian was lost in their own world.
Cindy leaned over and whispered in my ear "I bet he has a big delicious cock." and we both started giggling. After we ate mom and Jillian wanted to go shopping, so Cindy and I took a cab back to the cottage.
We quickly stripped down and put on our bikinis, Cindy was extra hot in a bikini that barely covered her breasts and crotch, her gorgeous little butt was on display for all to see. Cindy is Asian, 5' 3" or 5' 4" tall. Really slim, gorgeous eyes and short black hair. Like me she was born a male but lives full time as the woman she was meant to be.
I just hoped that I looked almost as good in my little yellow bikini as Cindy did in her hot red bathing suit. Mine was a little more modest than Cindy's but still showed off my body.
Cindy was checking out how she looked in the mirror when I walked up behind her and swatted her butt playfully. When she turned to look at me I grabbed her face and kissed her passionately.
As we were kissing my hand went to her crotch, I slide the front of her bikini aside and started rubbing her "clit." She was getting hard fast. So was I. My cock is small but the bikini I was wearing was smaller. We would have to take care of our erections before we hit the beach.
I slid to my knees and took her enlarged clit into my mouth. It was no trouble taking the entire length of her cock into my mouth. As I worked my mouth up and down her cock I reached around and started working one then two fingers in and out of her butt.
As I probed Cindy's ass with my fingers I was working my mouth up and down her cock, sucking hard on the head. It was not long until I was rewarded with a mouthful of delicious cum. When I felt her clit soften and slip from my lips I removed my fingers from her ass.
I gave Cindy a devilish grin as I licked my fingers clean then kissed her again. Cindy's hand went to my cock and she slowly started to work her hand up and down. My Clit was small but rock hard as I felt Cindy's hand start to message my balls.
She pushed me away and slipped to her knees. She engulfed my cock with her hot talented mouth. Oh God it only took about 90 seconds before I returned the favor and flooded her mouth with hot cum. Cindy raised up and kissed me pushing my own cum into my mouth. We kissed playfully pushing my cum back and forth until we had swallowed it all.
After we had settled down we both fixed our bikinis, grabbed a couple of oversized beach towels and made our way to the beach. We did not go far before we found a nice place to spread out our towels and started working on our tans. We had both lost our tans during the winter months and I was as white as I could be. I handed Cindy the bottle of suntan lotion and asked her if she would put some on my back. I was laying face down and had my eyes closed enjoying the feel of Cindy's hands roaming over my body. She was not just rubbing lotion on me she was giving me a very sensual message in the process.
When I opened my eyes I noticed that we had attracted the attention of two cute guys who were watching us. Cindy had noticed the guys also and when I raised my head she kissed me lightly. I told Cindy that it was her turn because I did not want her to burn either. The guys were inching closer to get a better look.
As Cindy laid face down so I could work on her back I squeezed a generous amount of lotion in my left hand and started rubbing down her shoulders and arms. I spread lotion onto her neck and as my hands started working down her back I undid the straps of Cindy's bikini top. I leaned down and kissed her shoulders. Her skin tasted like cocoa butter. I finished her back and I skipped down to her feet and started working my way up the back of her legs.
Spreading lotion and messaging my way up her legs, I noticed the guys were not even trying to pretend they were watching us. I smacked Cindy's cute butt and told her to roll over. As she did I straddled her hips. She was holding her top against her breasts as I squirted some more lotion into my hands and started running them over her ribs and across her tummy. My hands went up to cup and squeeze her breasts through her bikini top.
I felt a shadow and looked up to see the two guys who had been watching, standing over us. I smiled up at them as I noticed the bulges in their shorts. The two guys were Jamaican and had dark brown skin and dreadlocks. One of them was blatantly rubbing his crotch and it was an impressive bulge he was rubbing.
I smiled up at them and said hello. The talk Jamaican was 6' and introduced himself as James. He introduced his friend as Tyree. Tyree spoke up and said for us to just call him Ty. They both looked to be in their early twenties.
I rolled off of Cindy and sat up. I told them I was Andi and Cindy introduced herself. James seem to lock onto Cindy and it was like I did not exist. It was Ok because Ty was a hunk and he seemed interested in me. I scooted over and offered him a seat on my towel.
Ty sat down and I could feel his leg against mine. I looked over and Cindy was flirting with James. James already had his arm around Cindy and her head was resting against his chest. She had retied her bikini top but there was a nice bit of cleavage showing.
We sat there and talked, getting to know each other half the afternoon. When Cindy and I decided we needed to get out of the sun, James and Ty walked us back to our beach house. They were telling us about a hot night club that just opened and they asked us if we wanted to go to it with them tonight.
Before I could say anything Cindy had agreed for the both of us. Ty said they would be back by to pick us up at 9 o'clock that night. Then Ty took me into his arms and kissed me deep. I felt his tongue pass my lips and start to explore my mouth. Ty's hands were also caressing my back. Before he broke the kiss he slid his hands down to my ass and squeezed my cheeks.
I was thinking about dragging Ty to the bedroom and having him fuck me right then and there but I heard my mother ask who our new friends were. Embarrassed I quickly broke the kiss. I know I was blushing a dark red and Ty was acting like he had been caught with his hand in the cookie jar.
We made quick introductions and then the guys left saying they would see us tonight. When they were out of earshot Mom laughed and told Cindy and I that the guys were sexy and that it did not surprise her that we had already picked up some hot guys the first day here.
Later than night Cindy and I were getting ready to go out. Cindy had on a hot little black dress and a pair of 3 inch heels. I was going to wear a tight form fitting blue strapless tube dress, blue panties and a pair of tan open toed sandals.
Neither of us were wearing a bra. Since I had been on hormones for a while, my breasts had grown to a 32 C and I was getting close to moving up to a 34 so I wanted to show them off.
I had my long blonde hair tied up in a ponytail and my lips were painted a bright red. Cindy told me I looked like I was begging to get fucked. I just smiled and said "good I hope it works."
When the guys came to pick us up Ty was driving, so James and Cindy climbed in the backseat and snuggled very close. Ty kissed me on the cheek and opened the door for me. As I slide into the seat the hem of my dress rode up just a little.
When we got to the club it was packed with both locals and tourists. We had to wait in line just to get in. As we stood in line Ty kept his arm around me holding me tight to him. He really smelled great. I looked up and he leaned down to kiss me. We kissed several times before we got to the head of the line and they let us in.
As we entered the club it was crowded but Ty directed us to a table where an older gentleman was sitting. Ty looked a little like the man and I later found out he was Ty's Uncle named William. Ty order me a drink, some island concoction that tasted fruity. Apparently they do not check peoples ages in Jamaica.
I had to sip my drink slowly because it was very strong. It was not long until James pulled Cindy out to the dance floor. She was shaking her sexy body to the music. James was behind her grinding his crotch against her.
I was wedged into the booth between Ty and William. William kept telling me how pretty I was. Ty was kissing my neck and he had his hand on my thigh. Cindy and James came back and that meant that I was squeezed even tighter between Ty and William.
I told Ty I wanted to dance, more to get away from William than anything else. Ty reluctantly quit kissing me and removed his hand from my thigh and took my hand.
We danced to several songs, we were joined on the dance floor by Cindy and James and at one point Cindy and I were dancing together with James and Ty rubbing against us. I thought it was so sexy and I guess the strong drink was effecting me more than I thought it would as I reached back to squeeze the bulge in Ty's pants.
Finally I had to take a break, I grabbed Cindy and we headed for the ladies room. Cindy was talking about how nice James was and how she was going to have fun later. I told her I thought Ty was pretty hot. I fixed my lipstick and we headed back to the table.
As we approached the table, Ty and William were arguing. As we got close I heard Ty say "no way am I going to ask her to do that." William was leering at me. My hand slipped into Ty's hand and our fingers intertwined.
I asked Ty what was going on, and he said nothing. William was looking me up and down and then he turned to TY and said "You better get her to do it or you will regret it."
I again asked Ty what William was talking about. Ty said come on, lets get some fresh air. Ty led me out a side door into an area where people went to smoke. We walked over to an area where there were no many people and I said "so are you going to tell me what William was talking about or what?"
He started, then stopped several times. "I owe William a lot of money, He got me out of a gambling debt and probably saved my life. He said he would cut the amount I owed if you would....you would give him a blow job."
I just looked at Ty.
"I told him I would not ask you to do it."
"Ty how much do you owe him?"
"$10,000."
"Andi, I am not getting you involved in my problems. I think we should get Cindy and James and just leave now."
When we went back in William was waiting for us at the table. James and Cindy was nowhere in sight. William said they were at the bar. Ty said we should go look for them. I told James to go and that I wanted to talk to William.
William's eyes lit up. Ty looked like he wanted to hit him. I said "GO find James and Cindy. I will be fine."
Ty stalked off as I slide into the booth beside William. I reached down to squeeze and rub the bulge in Williams crotch.
"How much are you going to reduce Ty's debt if I give you the blow job you want so bad?"
William smiled brightly, "I will reduce it by $500."
I unzipped his pants and smiled at him seductively. "That's it? I bet you can do better than that."
I pulled his cock free of his pants and slowly worked my hand up and down. Gee it was a small cock. I almost laughed at him.
His breathing had increased. "Ok $1,000 but we cant do it here. We will go out to my car."
"I am sorry Ty will be back soon, so its now or never." Squeezing his cock I looked around to make sure no one was watching us closely then I leaned down and licked the head of his cock.
William moaned. "You are freaky. You need to dump Ty and go home with me."
That made me mad and I guess I squeezed his balls a little to hard. William groaned in pain. I asked, "Do we have a deal? Or do I get up and walk away?"
"No don't go..please.."
I knew I had him so as I started working my hand up and down his small cock I leaned down taking the head into my mouth. I sucked on the head and swirled my tongue around it.
I started bobbing my head up and down his cock. I varied the pace at which I sucked Williams cock. Some times it was slow and sensual, then it at times I bobbed my head up and down quickly. I heard him whisper oh God, then he started shooting a load of cum deep into my mouth.
I pretended to swallow his cum then I lifted my head. Smiling at him I leaned in like I was going to kiss him. Instead of kissing him I opened my mouth to let his cum spill out onto his chest and expensive shirt. At the same time I took his drink and poured it into his lap.
William was cussing as I scooted from the both in time to see Ty, James, and Cindy coming toward me. Ty asked what was going on and I just smiled and said that William had an accident. I think Cindy caught on to what I did and she was laughing hysterically.
When we got to the car, Ty spun me around to look at him, "You did it didn't you? After I told you not to."
"Ty I was helping you plus I seen a way to humiliate William in the process, he need to be brought down a notch."
He still seemed mad as he did not say a word on the drive back to the house. I tried to cozy up to him as I laid my head on his shoulder. My fingers played across his chest and eventually found their way into his lap.
He seem to be warming up again as I started rubbing his crotch. It had went down since we were on the dance floor but with a little effort he was rock hard again. When we pulled into the drive and Ty put the car in park, he leaned over and kissed me deep. We kissed passionately for a long time, until Cindy tapped the window and asked if we were coming inside with her and James.
Cindy and James were already on the bed making out, James had his hand up Cindy's dress and she was fumbling with James' zipper. As I was standing there watching them, Ty came up behind me and I felt his arms around me. He started kissing my neck, biting my ear. His hands came up and he pulled the top of my dress down to my waist.
Ty's strong hands cupped my breasts and his finger started rubbing and pinching my nipples as he kissed my neck and started grinding his crotch into my ass. I felt a huge bulge and decided I needed his cock now.
Cindy had James' cock out and was smothering it with kisses, it was hard and had to be over 7 inches long and thick. I pulled away from Ty and slipped my dress the rest of the way off. I kicked off my sandals and stood there in just my blue lace panties. James was laying on his back as Cindy was working her mouth up and down his cock.
I watched for a few minutes and when I looked back, Ty had undressed and was standing there naked. His cock was throbbing and leaking pre cum. It was longer than James, easily 8 inches but was not as thick.
I reached behind me and started stroking Ty's cock. He reached out to slide my panties down. He pushed his hips forward wedging the head of his cock between my ass cheeks as he reached around and felt my "clit" for the first time.
He pulled back a little and I was afraid he was going to have a bad reaction. He turned me around and stared at my small cock.
I all but begged, "please don't be mad. I did not mean to deceive you."
He smiled at me, "I'm not mad, just surprised, you look so feminine and beautiful."
James was staring at me. Then he asked Cindy, "Are you like her?"
Cindy pulled her mouth off of James cock, "Yes I am."
James laughed, "I have to see it, strip for me."
Cindy crawled off of the bed and stood beside me. I told her, "here let me help you." and reached out to unzip her dress. I slipped the dress off of her shoulders and started sliding it down, as I did I kissed her shoulders and licked the soft skin between her shoulder blades.
I slapped Cindy on the ass and told her to step out of the dress. I laid the dress across the back of a chair and turned to watch Cindy wiggle her sexy butt and working her panties down her legs. Cindy was standing there and looking incredibly sexy wearing nothing but her high heels. James was stroking his cock slowly as he told us that he wanted to see us make out a little bit.
Cindy smiled at me as we hugged each other and started kissing lightly, her hands went to my butt and pulled my body tighter to hers. I felt my sensitive nipples rubbing against Cindy's and the feeling was very erotic. when our clitties touched I moaned loudly into Cindy's mouth.
Ty came up behind me, James was behind Cindy, they started pulling us apart. We reluctantly let go of each other. James asked me where the lube was, he didn't ask if we had any, but where it was. I opened my purse and handed the tube to Ty.
He spread some on his hand and started working one then two fingers into my ass. I let out another moan as Ty inserted a third finger. As Ty was doing this, he reached around to play with my clit. Ty handed the tube to James and as he started to finger Cindy's ass Ty pushed me down onto all fours. I took a deep breath and prepared to take Ty's cock.
I pushed out as Ty pressed his cock head against my anal ring. I moaned again as the head entered me. Ty started working his cock in and out of my slowly. Cindy was still standing in front of me as James had her bent at the waist and was starting to work his cock in and out of her ass.
As Ty pushed forward he pushed me into Cindy's crotch, it was just natural to open my mouth and to take Cindy's cock into it. James and Ty got into a rhythm and each time they pushed forward it pushed Cindy's cock deeper into my mouth.
Soon I heard Cindy let out a squeal and a giggle, then she came in my mouth. As Cindy came James pulled her away and bent her over the side of the bed.
Ty had started to ram his cock in and out of me. James was fucking Cindy hard and rough. As Ty fucked me I started playing with my clit. It was not long until I came hard, spraying a small amount of cum all over my hand. I came so hard I was dizzy and seeing stars. It did not slow Ty down any as he continued to fuck me at a rapid pace.
I heard James let out a low growl as he rammed his cock deep and emptied his cock into Cindy's ass. Ty was a stud with Stamina. He continued to fuck me hard.
As I started to recover, I seen that Cindy was on the bed and she was cleaning James' cock with her mouth. Ty fucked me for another ten minutes before I felt his cock get bigger then he was cumming in my ass. Ty held his cock deep into me until he had finished.
As Ty pulled out of my ass I started to get up but James told me to stay where I was. I looked up at him and his cock was rock hard again. He got behind me, entered me easily, and soon he had buried his cock into my cum filled ass.
Ty was pulling Cindy down to the floor. He had her kneel in front of him and she started sucking his cock. Her ass was all but in my face so I did what any cum whore would naturally do. I moved a little closer and started darting my tongue in and out of her sweet ass.
We had formed some kind of chain. James was fucking my ass, I was licking and tongue fucking Cindy's ass and Cindy was sucking on Ty's hard cock.
Ty pulled hid cock from Cindy's mouth and turned her around to where we were facing each other. Ty rammed his cock into Cindy and when he pushed forward we almost butted heads. Ty and James continued to fuck us but now Cindy and I were kissing.
The guys were fucking us hard and rough but we manage to continued to kiss each other. All four of us were covered in sweat and Cindy and I had cum on several parts of our bodies. James was huffing and puffing, the poor guy would not hold out much longer. Ty was in great shape and he continued to fuck Cindy at a rapid pace.
I heard James say "Oh Shit, here it cums" right before he started shooting cum into my ass. Ty laughed at him and continued to ram his cock into Cindy. Cindy was moaning loudly now, James cock had gone soft and popped out of my ass. James got up and went to the bathroom. Ty let out a loud groan then to my surprise instead of cumming in Cindy's ass he pulled out and shot his load all over her back.
When Ty was finished cumming I think he got embarrassed a little because he started dressing quickly. James was already dressed and like most guys, they could not leave fast enough. They left without even a good bye kiss. I told Cindy I doubted that we would hear from them again and we both laughed.
I crawled onto the bed with Cindy and kissed her again. We really needed a shower but we were both tired and soon we were snuggled close together and we both drifted off to sleep in each others arms. ____________________________________________________________________
It was late the next morning when came into the room waking us up. She was wearing a short red robe. with a sexy black lace teddy underneath it. Mom is 5'2" tall, 120 pounds, she has short red hair and dark green eyes, the top of Her 34B breasts were visible.
We must have looked a mess. Mom just stopped and stared. Cindy grabbed the sheet and tried to cover up. I laughed at the expression on Mom's face. I could see her trying to look stern. I jumped out of bed and hugged her and told her Good Morning. And then I kissed her. It was not a mother-daughter Kiss, but a kiss between lovers.
Mom tried to resist and it was her turn to look uncomfortable. I asked mom where Jillian, her boss and girlfriend, was at. She said that Jillian had went into town to make a conference call. Even on vacation she had to take care of work.
I got a wicked idea and as I kissed her again I undid the sash of Mom's robe. I noticed Cindy was looking on with interest as I slid the robe down her shoulders and off. Mom tried to pull away as she said, "Stop that now."
"Oh Mom you can't really mean that." Kissing her again while caressing her back.
"But please...not in front of Cindy."
Slipping one of the straps of her teddy down her shoulder I whispered, "She will be doing more that watching if I have my way."
Mom blushed a deep red as I slid the other strap off of her shoulder exposing mom's perky breasts. Cindy got off of the bed to join us. I turned Mom to face Cindy and Cindy took Mom's face into her hands and kissed her.
"Please..Andi....Don't Do this to me.."
As Cindy kissed Mom again I reached down to take the belt from Mom's robe. I pulled Mom's arms behind her back and tied her wrists together. Cindy giggled as she bent her head down to suck on Mom's right nipple.
As Cindy was going back and forth sucking one nipple then the other nipple I push Mom's nighty over her hips and it hit the floor. I reached around to work a finger into Mom's cunt and between what Cindy was doing to her breasts and my fingers in her pussy, Mom was already soaked.
We both took an arm and led Mom to the bed forcing her to lay on her side. Cindy crawled around until they were in the classic sixty-nine position. I watched as my closest girlfriend started licking mom's pussy and Mom was licking Cindy's cock. While they were going at it I slipped out of the room and sneaked into my Mom's and Jillian's room.
I went to Mom's suitcase and I found her special "Make up" case. The case actually held her adult toys. I took the case back to where mom and Cindy were still going at it. As I entered the room Mom had gone stiff and was cumming hard.
When She came, Mom let Cindy's hard cock slip from her mouth. When Mom finally regained her senses she looked up at me to see my "clit just inches from her mouth. Cindy smacked mom's bare ass and told her to suck me.
Mom opened her mouth as I pushed my cock past her lips. I was fucking Mom's face while Cindy started going through the toys. She found a thin eight inch vibrator and I watched her take it and pushed it against Mom's pussy. It went into her easily. Cindy worked it in and out of her for a few strokes, then pulled it free.
Cindy took the vibrator and forced it into Mom ass. Mom moaned as Cindy pushed it deep and then turn it on. She left it there. I was so close, my small cock was so hard. I could not hold off any more and I came in Mom's mouth. My knees almost gave way when I came so I sat on the edge of the bed.
Mom was pleading with Cindy to remove the vibrator but Cindy just laughed and continued to looked through the case. Next she held up a pair of nipple clips. I seen Mom shudder. Mom was trying to work her wrists free as Cindy attached the first clip to her right nipple.
I was standing close to both of then and Cindy gave me an evil grin and attached the other clip to my left nipple, it hurt like hell and I let out a loud moan. I was now connected to my Mom by a thin metal chain.
Cindy whispered in my ear, "I want to watch you fuck your Mom."
"MMMM that sounds hot but after last night and then with Mom sucking my cock, With the hormones, I don't think I can get hard again for a while."
Cindy smiled again and dumped the case out onto the bed. She picked up Mom's strap on, a 10 inch fake cock that was big around. "Here use this."
"Uh why don't you do it?"
Mom spoke up and was pleading again, "Why don't you two just forget it and let me go...please?"
Cindy looked at me, "You really don't mind me fucking your Mom?"
Mom looked so embarrassed listening to us discuss who was going to have sex with her. I reached down and caress Mom's pretty face. "You want to be fucked by Cindy don't you?" Mom just whimpered.
I unhooked the clip that was attached to my nipple. and attached it to Mom's free nipple, she groaned again and wiggled on the bed. I rolled Mom off of her side and laid her onto her back. Cindy crawled between Mom's legs.
I slapped mom's thigh and told her to spread her legs farther apart. Mom did as she was told. I squeezed Cindy's cock as I positioned it at the open of Mom's cunt.
Cindy pushed forward and her little clit enter Mom. Cindy started working her clit in and out of Mom as I backed away. I kneeled beside the bed and picked up the strap on that Cindy had held up earlier. I started deep throating it coating it with my saliva as Cindy continued to fuck Mom.
Mom started thrashing around on the bed as I took the strap on and started working into my ass. My eyes were glued to Mom's pussy. It was so erotic to watch Cindy's clit working in and out of Mom's cunt. I took the strap on and pushed it into my ass. One hand was working the strap on in and out of my ass while the other hand was cupping my breasts and pinching my nipples.
Cindy push forward and stayed there, she leaned down and kissed my mom forcing her tongue into Mom's mouth. I noticed cum leaking from Mom's pussy as Cindy collapsed on top of Mom.
As I watched this I had a dry orgasm that send shivers and chills all through my body. After we all settle down, Cindy took the clips from Mom's breasts and untied her. I removed the strap on from my ass and pulled the vibrator from Mom's. The batteries were all but dead. We all shared several kisses the we all headed for the shower in the master bedroom.
It was crowded but we all had fun washing and caressing each others body. We were all to tired to do more than play a little and when we were all clean Mom dressed and left to go meet Jillian.
Cindy and I crawled back in bed and snuggled closed then drifted off to sleep again. ________________________________________________________________________
A Note for all those who like the Andi Series. I know the chapters have become fewer and farther between each posting. I am not ending the Andi series entirely but I am taking a break from Andi for awhile. I thank everyone for their emails of encouragement and support and I urge everyone to check out my Jasmine series in the Trans gendered control section of nifty.org.
Thanks again everyone.