Wedding Night – Olive and Liam
Olive was a sweet little femboy standing in front of the bathroom mirror getting ready. His makeup was completed and his large beautiful dark eyes shone brightly as he examined himself. His true love waited on the other side of the door. The man was taking Olive on a special trip tomorrow to get married. But the wedding night was tonight… in just a few minutes in fact. He was so excited he could hardly breathe. He was wearing the special outfit that Liam bought him.
Olive felt so beautiful. His tiny little pecs were covered by a sheer see-through bra. The straps were a pale pink lace that not only kept the bra up but outlined his nipples in sweet pink triangles. His tiny nips were still tingling from being washed by his lover in the shower a little earlier. His panties were the same pink lacy design with a tiny horizontal slit in front. Through this opening, his slender little peter poked upward and slightly forward. As instructed, Olive had tied a pink lace bow around it, just behind the head. He twisted slowly left and right and watched his tiny little dicky move back and forth as if searching for something. Olive smiled at the thought. He knew what his hungry little peter was looking for… his lover’s warm mouth. His peter jerked upward at the thought.
His little balls could be seen as pale shadows inside the sheer panties. There was no dark hair to obscure the view, Olive was hairless. His master had shaved him once again just before Olive had started to get ready for this special night.
The thin garters on his thighs as well as his fingernails and toenails were the same lovely shade of pink. He looked like a delicious pink and white dessert. Just yummy!
He was wearing a small part of his wedding gown… the veil. It was hung from a beautiful diamond comb in the top of his long dark hair. There was one ultra-sheer layer that surrounded his face and reached his chin. It framed but did not hide any of his beautiful facial features. He felt like he was inside a cloud. He felt like an angel. He was! The rest of the dress was packed away for the trip. He was going to be such a beautiful bride tomorrow.
Olive turned to the side to check out his figure in the mirror. His bottom had the most wonderful shape. His butt was so firm that he could barely get the cheeks to open enough for Liam’s fingers and tongue. Tonight his special little hole would have to open really wide. Olive was not going to be a virgin for much longer. He knew that his master would be take his time and be very gentle with him… as always. Even knowing this, he was still nervous. He shivered and goosebumps traveled up his legs and across his belly. He hiccupped anxiously several times making his dainty penis bounce each time. The lacy bow tied on it looked like it was a flag waving its surrender.
He faced the mirror again and his hand traveled to his heart. There hung the special wedding gift from his true love, a beautiful gold locket. Inside was a small tuff of the hair removed earlier from around his little cocklet mixed with some of his master’s hair. He took the locket in his hand and brought it to his soft lips. He kissed it. They were already joined in his mind. He smiled and opened to door to the rest of his life.
SHE was ready.
I noticed that the teen clerk at the dry cleaners was paying special attention to me. The strangely handsome teen only seemed to work on weekends and late on weekdays so he was probably still in high school. His name tag said “Oliver” and he was slender, black-haired, and always seemed to be wearing a baseball cap. One night late, I happened to look back into the side window after dropping off my laundry. Oliver had his face pressed into my dirty clothes. At the time, I said to myself: “What a sweet little pervert!” I figured he did it to all the stuff being dropped off. He appeared to be a hard worker, so I decided not to say anything.
One day I was interviewing applicants for a stockroom opening and into my office marched Oliver. He was dressed much better than I had ever seen him before. Without his cap, his dark hair was longer than shoulder length but it was pulled into a neat ponytail down his back. I looked down at the application. He was 18 and had been part-time at the other job for about a year. He had recently graduated and wanted a full-time job.
I had much more qualified applicants for this position but by the time I had finished speaking with Oliver, I had had a brainstorm. I offered him a job helping me at home. I explained that I worked such long hours and was often traveling to the other branches, even out of the country; that I needed a house sitter and errand runner. I could pay him more than he was making now and the job would include free room and board. He would have his own room at my house and the use of one of my cars.
Oliver started smiling even before I finished. He stood and offered his hand. I shook it, remarking how soft and wonderful it felt in my hand. “Thank you, sir” he said politely.
Over the weekend, Oliver moved in.
Oliver really impressed me. He worked hard and followed up. Every task I gave him was done correctly. I liked him. I told him he was doing a great job. He beamed with happiness.
That all seemed to change when I returned home early from a trip. When I walked into my house, a girl ran. Oliver had brought a girl to my house while I was away! I was furious! I went looking for him.
When I entered his room, I found Oliver cringing behind the bed. He had removed the dress he had been wearing but that just exposed his tiny bra and bikini panties.
The GIRL had been HIM.
I was shocked. I saw that he had on makeup… which had run because he was crying. I told him to clean himself up and come to the den. I would be waiting. He had not shown up after 30 minutes so I returned to his room. He was nearly packed and was still softly sobbing. Poor boy.
I had him sit down and we talked. I told him I did not want him to leave. I told him I liked his work and, even more important, I liked him and enjoyed having him around. I told him that I did not care that he dressed up as a girl. In fact, he was welcome to dress up anytime he wanted, even when I was home. I told him that to prove how I felt, I wanted him to dress up again as I wanted to take him out to dinner. Just the two of us. To a really nice restaurant.
As I talked, his sobbing slowed and finally stopped. He wiped his face and a strange calm came over him. He thanked me and told me he would be happy to go out to dinner with me. I left.
When Oliver walked out of his bedroom later, I was stunned. She was spectacular! She was such a beautiful young woman. She walked gracefully to me, offered her hand and said “I am Olive, nice to meet you.” Her voice was low and soft and very feminine. My mouth gaped in astonishment. I eventually recovered and took her hand in mine but not to shake it. I just lightly pressed her hand and let it go. I e****ted her to my car, opening the house door and then the car door for her as she nodded her thanks each time. Dinner was magical. When we returned and were about to separate to go to our respective bedrooms, she drew near and lightly kissed my cheek. Olive told me “Thank you for a wonderful evening. Good night, sir.” I mumbled something and watched her walk away. Her figure and, especially her ass, were perfect. I could not fall asl**p for the longest time, thinking of Olive asl**p on the other side of my house.
The next morning Oliver was dressed normally. We had a long series of talks over the next few weeks and I found out more about the lovely Olive.
His single dad had gotten a job in another state and had to move. Oliver wanted to graduate with his friends so he wanted to stay. His dad had a suspicion about “Olive” and was glad to leave him behind. Oliver had been staying with a buddy to finish school but the friend had started to become suspicious too. He had no real place to return to. He was very alone. Working for me and my traveling had given him the perfect position to bring Olive to life. He was dressing up every chance he could. He spent hours perfecting his makeup in his room at night. He even slept in frilly nighties.
I told him about catching him smelling my clothes and he nearly had a fit. After he calmed down, he told me that my clothes were the only ones he did that with. I asked why. He dropped his eyes and explained that he found me very attractive and he had been having dreams about me. He found he loved my fragrance and it helped with his fantasies. He told me applying for a job at my company was not by chance. He planned it because he wanted to be close to me. He was shocked and pleased that everything had worked out as it did. He loved being with me.
I had long ago told him to call me Liam and we now decided that he would be called Oliver when he was dressed as a boy and Olive if he were dressed as a girl. We were both pleased at this solution. We also decided that after nine o’clock every night he could dress as Olive unless I had guests over. We both like that too. I was going to see him in some of her little nighties and she was going to get to model them for me. I was looking forward to that!
I was quickly falling in love with Olive. I found that she obeyed me absolutely when she was Olive. She did not call me Liam; I was “Sir” when she addressed me. I would sometimes call her “Honey” or “Sweetie” and the like; she smiled so broadly when I did.
Late one night, I had her sit beside me as we watched TV. I took her little hand in mine. I could feel her shiver.
Liam: You are shivering, baby. Are you cold?
Olive: Maybe a little.
Liam: Let me put my other arm around you. Here Olive, snuggle close.
Olive: Thank you, Sir.
I took one hand and played with her fingers. Her shivering increased. I hugged her tighter. She turned her pretty face to mine and I kissed her. She melted in my arms. Later, I carried her to my bed. That night, we only kissed and cuddled. We fell asl**p in each other’s arms. Extra warmth in my bed and a sweet gentle breath blowing on my face woke me. The first thing I saw was this beautiful little angel sl**ping peacefully beside me. I eased out of bed and went to the bathroom. When I returned, Olive was gone. When I went to the kitchen for breakfast, Oliver was looking out the window with his back to me. I walked up to him, kissed his neck, and said “Morning Beautiful”. He spun around and kissed me so very hard. When he finished, he said “I thought you might regret last night.”
Liam: Baby, the only thing I regret was waiting so long.
Oliver took my hand and led me to his bedroom. Olive soon emerged from the bathroom. She was wearing her prettiest nightie.
Liam: You look dirty to me.
Liam: You need a shower! (Said with a grin.)
Olive: Yeah! (Said with relief.)
We stayed in the shower so long, the water started to run cool. First, I just looked at him, he was beautiful. He had long slender muscles like a swimmer. He had curves in all the right places. His perfect little nipples were hard. He had a slender, short penis with a tiny tapered head. The little collar surrounding the head was dainty. Hanging from the base of his pretty peter was the tiniest little sack I could imagine. The balls inside it were like petite marbles. The skin surrounding them was so extremely tight that there were no wrinkles.
The hair on his body was sparse and soft. I dropped to my knees and washed his privates gently and softly, giving them my full attention. I discovered that his little balls were as sensitive as his penis. His little toes flexed as I stroked his tiny sack. I gently fondled the perfect little shaft using my soapy thumb and index fingers. When I tickled the tiny pink head, he jerked and gasped.
I rinsed him well and gave his femboy penis a sweet kiss on the very tip. I stood up and held my cock out to him. He dropped to his knees and stared at my cock for the longest time. His eyes were wide and he softly panted. I have to admit my dick is larger than the average. It measures nearly nine inches when hard. It was already throbbing and growing. My balls are large and egg shaped. His little hands soon had my cock as hard as a rock. He played while I struggled to keep from exploding over his head onto the shower wall. I rinsed well and nodded to him. He put a little butterfly kiss on my cockhead. Shockwaves spread to my brain, to my asshole, everywhere!
I stood up and had him turn around. I washed his back and then his firm shapely bottom. He had a perfect curvy shape with the two deepest butt dimples I had ever seen. His little ass was so smooth and but so firm. My fingers gently squeezed him and held him. I had him bend forward. I got on my knees and spread apart his butt cheeks… with some difficulty I have to say! I used one of my soapy fingers to wash along his groove from his back down to his petite sack. I washed his tiny asshole with just my fingertip. I spun my fingertip in tiny circles around his special hole. He moaned so sweetly. I rinsed him and gave his tiny hole a soft kiss.
I had him face me and I turned away and bent over. I reached back and pulled my bottom apart. I soon felt his small fingers washing between my butt cheeks. He rubbed my hole with his tiny fingertips and gently inserted the tip of one into my bottom. He was a wonderful boy-girl. He then rinsed my bottom and kissed my love hole. Gosh, he was so amazing.
I washed the rest of his little body with my soapy hands. He did the same for me. Soon we were snug in his bed. I was already exhausted but excited as well.
I kissed his beautiful little peter. I took his little balls in my mouth. I sucked on them gently. I nursed on his peter like it was a nipple. I slid my lips up and down it. I scrapped my teeth up and down it too. He screamed… but not from pain. He was overwhelmed with the pleasure. He made his cute little peter slide in and out of my mouth. I bit gently and he screamed again… even louder. He whimpered, he cried, he went a little insane. I would not him cum even though he begged and pleaded.
I sat on the side of the bed and had him kneel between my feet. I spent at least an hour showing him how to use his sweet mouth on my throbbing cock. It was bright red while he worked on it. It had never been as big as this. I was so pleased with my new lover. When I figured it was time, I unloaded in his mouth. He gagged a little, but quickly recovered. At my urging, he sucked and swallowed, swallowed and sucked, drank and drank. My big balls fed his flat belly. He felt full… of love. I felt exhausted… and happy.
Over the next few months, we explored every aspect of love making except putting my cock in his little ass. I even let him fuck me. He followed my directions perfectly. I was in control of my special guy, or was it special gal. Who cared! I was in love with my wonderful friend! And he loved me.
He started calling me “master,” especially when he wanted to feel helpless and needed to be cared for. We had such a special bond.
On his birthday, I took him out for a special dinner. I had bought Olive the most wonderful dress for the occasion. She looked more beautiful than I had ever seen her. I got on one knee and proposed right at the table. My lovely Olive said “Yes”. The other diners clapped and cheered.
Olive entered the bedroom. Light from the candles bathed her body with warmth. Her veil seemed to make her mysterious. The bow on her little peter bounced slowly as she walked to her sweet lover. Her master was naked and hard and standing by the bed. She approached him and stopped just in front. He lifted her veil as he was going to do again tomorrow and kissed her.
Liam: Sweetheart, I love you with all my heart.
Olive: My soul is yours. I am so happy to be with you.
Liam: Are you ready to give me your special gift?
Olive: Take me, my love. I am ready and eager.
Liam: It may hurt a little.
Olive: It will make feel like I am part of you. Like I am yours. Go deep, go hard, go fast, make this last part of me your very own. I surrender my all.
He guided her with his strong hands as she lay down across the pillow. Her sexy bottom was presented to him like a gift. It was! He sprayed some baby oil into her little hole. His big cock followed. Olive grunted as her master’s big cock head popped inside. Little happy tears ran down her cheeks as she urged him on. He pushed. She pushed back. They thrust and shoved at each other until Liam was as deep inside his dazzling femboy as he could manage.
She couldn’t take it all; the little hole was too virgin to do that yet. But it would learn; she would learn; they had plenty of time… a lifetime.
He gently made love to her. He went faster and faster. She squeezed his big cock gently with the muscles in her tail.
He stopped while deep inside and taught her how to milk him. He had her squeeze her little ass tightly and hold that squeeze while he pulled back until only the head was inside her. He had her relax while he went deep again. Squeeze during the “out” motion; relax during the “in” motion. Squeeze/out, relax/in. Over and over. He told her that she was such a sweet student.
Liam pulled out completely several times and watched Olive’s sweet hole slowly close. What a wonderful sight. He would then insert his cock head back inside her. She whimpered softly each time the cock popped inside. She was so special!
Liam was so full of cream he ached. He felt like he could squirt a gallon of love. He had a short fantasy of it traveling all the way through her and filling her pretty mouth and ass at the same time! He couldn’t hold it any longer. His cock exploded.
When he sprayed his love cream inside her, she climaxed too. Her sugary juice gushed onto the pillow. Afterward, she cried in his arms. Tears of happiness. Tears of love. They slept.
Tomorrow was a very important day.