First Day at Boarding School
- 1 year ago
- 11
- 0
Scene Four At The Boarding School free porn video
Christmas break at the Boarding School.
It was December 15th, the dorm was empty and I was alone in my room.
My parents sent me away to an all-male College/Boarding School in the Northeast, USA. They suspected I was Bi or Gay and wanted me out of sight and out of their way. They informed me I would be in school until the summer break.
My name is Timmy. I am eighteen years old. I am green eyed, five foot ten, one hundred forty pounds, quite skinny, very feminine looking and not well endowed with only a five inch thin cock but I am told I have a great ass. My body has zero hair except on my head which is blond and on the long side. The only area I need to remove hair is on my pubic area and that is very light blond. I love to wear pantyhose and panties because they feel good on my skin and I feel so sexy when I do. I am comfortable as a closet cross-dressing young man. Many have said my face is so pretty I should have been a girl and I agree. That is why when I am servicing someone I call myself Tammy.
That day I was feeling low because all my friends went home for the holidays. I hadn’t had sex for three days and was sitting on my bed and feeling very horny. I had just reached inside my shorts to stroke my boner when my cell rang.
“Hello, Timmy,” Mrs. Longinbeckerstien said. “I hope I am not disturbing you on this crisp Saturday morning.”
Holly shit why is Mrs. L. calling me I wondered? “Hello Mrs. L.”
“Timmy or should I call you Tammy,” Mrs. L. said.
My brain was screaming, “What the fuck is happening?”
“Your silence is speaking volumes Timmy. Don’t be frightened, I know all about you. My husband shares all the videos with me. Oh, I guess you hadn’t realized his office has cameras to record all his adventures. I watch them every time as he pleasures me. Timmy I am not calling to embarrass you but I am calling to ask a favor.”
“Sure anything you want Mrs. L.”
“Call me Vicky and when you talk to my husband call him John.”
“Tonight we are hosting a cocktail party for our closest friends and some work associates. One of my staff has come down with something and can’t help with our guests. Suzy is a tall young thing and we figured Suzy’s maid outfit will fit you quite well. Come over our home at six this evening. I will help you with hair and make-up and get you dressed. Is that alright with you, Tammy?”
Good God is that all right? My cock was hard as a rock as I feverishly jerked off as I stammered, “Yes, Vicky whatever you want.”
“Good then, see you at six,” she said, as she hung up.
I only stroked my girly cock a few more strokes when I erupted all over my belly and hand. I brought my cum drenched hand to my mouth and savored my sweet load.
I couldn’t wait until it was time to leave. I showered, then made sure what little velvety blond hair had sprung up on my pubic area was removed. I used my electric Epilady Hair Remover. It lasts longer and I don’t get those red bumps you get when you shave.
I put on a pair of hip hugger black silk see through panties and over that jeans and a pullover shirt. Grabbed my coat and gloves and headed cross campus to the Dean’s residence.
I was shaking with excitement when I rang the doorbell.
A young woman answered the door. She was wearing a maid outfit. She looked great in a low cut black corset top, French style short skirt, black stockings with garters and high heels.
She told me to enter and follow her. I obeyed like a little puppy dog.
She led me to a room off the kitchen. It was a separate maid’s quarters complete with bedroom, bath and a kitchen.
She told me to sit at the dressing table and wait.
“Hi Timmy or soon to be Tammy,” Vicky said.
I turned to see a really beautiful woman standing at the door. She was a tall redhead with a perfect body. She looked about thirty years old. I thought if I was a woman I would want to be her.
Vicky went to work on me. She applied makeup, lipstick, and a red wig. I must say I looked like a sweet virgin school girl. I wasn’t a virgin anymore, at least with men.
She then helped me with my outfit. It was the same as the maid who let me in at the door. The corset actually made my chest look like I had small breasts. It slimmed my waist even more then my twenty two inches. It also made my hips appear bigger. My legs looked long and beautiful in the shear black stockings and four inch heels. I looked in the full length mirror and saw a really hot girlie boy.
Vicky explained, “You are to serve the guest drinks. You are also to cater to their every need. You have catered to my husband’s needs along with the needs of some professors and most of the rugby team so I am sure you understand what I mean. Do we understand each other?”
“Yes Vicky, I believe I do.”
At that point my little cock sprang to attention pushing up out the top of my panties but was restricted by the tight maid skirt.
The guests arrived on time. I knew some of the professors but no one else. I served drinks for about two hours before things started to heat up. The guests were getting loud. Some were groping each other or even feeling up the other maids.
That is when Mr. L. (John) pulled me to him as he was seated in a big wing back chair. He sat me on his lap and put his hand behind my neck. He then gently guided my face to his. He kissed me tenderly on the lips and then slipped his tongue into my mouth. It was a kiss with passion. A kiss that said more is expected.
As he continued to kiss me I opened my eyes to see Vicky smiling at me. She winked and nodded yes. I closed my eyes and kissed John back.
We broke the kiss. I knew what I wanted. I slide to my knees between John’s legs and began to unzip his pants. I felt the entire room looking at me. A hush fell over the entire party as I pulled John’s thick hard cock free.
I held him in my hand as I admired his manhood. I then bent and kissed the tip of his beautiful cock. Pre-cum was leaking out and I scooped it off with my tongue. He stood and removed his pants and underwear and then his shirt. He was naked before me. I reached around him and held his buttocks firmly as I pulled him to my eager mouth. I engulfed his cock until my nose was touching his pubic hair. He held my head as I started to bob my head up and down on his erect eight inches of hard thick man meat.
I felt him tighten up and knew he was close. I was the star of the show now. I reached between his ass cheeks and placed my finger to his rose bud. That sent him over the edge. I pulled his cock out until just the tip was resting on my tongue. I pushed into his ass and massaged his prostate. He exploded sending a stream of white hot juice to the back of my throat. Then five long ropes of cum landed on my outstretched tongue.
I looked into John’s eyes as I happily swallowed his entire sweet load.
The room burst into cheers and applause.
I feel to the floor on my hands and knees. I raised my ass high in the air and waited.
I didn’t need to wait long. Someone pulled my panties down and off exposing my perfect heart shaped ass. I had reached under and pulled my cock and balls forward so all the guest saw was my ready and willing boy pussy.
Vicky said, “Wait a minute.” She came over and applied gel to my cunt. She expertly pushed some in as she fingered my waiting love tunnel.
The first man of the night lined his hard cock to my opening. He pushed roughly in. His cock was about seven inches long and his thickness was on the average side. He pumped vigorously for several minutes when he announced he was coming. He shot his burning hot load deep into my bowels. Then just as quick he pulled out. I never knew who he was as my face was buried in the carpet.
He was quickly replaced by another. His cock was thicker and longer. I must say it did hurt as he relentlessly pounded with all his might until he also came.
I looked around and saw the same happening to the other maids. What shocked me was all were girlie boys like me. The wives of the guests were watching. Some were taking pictures. Some were making out. Most were in a state of undress.
One of the guests slid under me in a sixty nine position. He kissed and sucked my willing little boner as I took his long hard cock to my mouth. While we were enjoying several other male guests lined up and had a turn in my ass. I was in sissy slut heaven.
The guy I was sucking tasted so good I was lost in passion. My ass was being filled for the sixth time when I couldn’t hold out any longer. The guy I was sucking sensed this and we came at the same time. We each swallowed repeatedly but not before savoring the taste and texture of each other’s cum.
The guests all had a great time. Men enjoyed men and the women enjoyed women.
At about two in the morning the last guest left. The other maids cleaned up but I was asked to come up to the master suite.
Vicky said, “Please sleep with us tonight.”
We undressed and went to the shower together. Vicky and John washed themselves then they washed me. They even toweled me dry before we adjourned to their king sized bed.
I was in the middle. John kissed my nipples as Vicky kissed me on the lips. This was my first real kiss by a woman. It was very nice. We continued to kiss as she ran her hands over my entire body. I likewise felt my first breasts and touched my first pussy.
Vicky moved to her back as she guided me on top of her. John held my little dick in his hand and placed it to the edge of her slit. Oh my God I was going to fuck a woman.
John pushed down on my ass and my ready cock pushed into her folds. It was like pushing my cock into a tub of softened butter, only better.
I moved in and out as she met my every move with her own. We were actually fucking. I kissed her and she kissed me. It felt like we fucked for hours but I’m sure it was only minutes.
I screamed out as I exploded. That set her off as I felt her vagina clamp down around my penis. She actually worked her muscles to force out all my potent seed.
I lay in her arms for a long time as our heart rates slowed. When I rolled off John took my soft penis in his mouth and cleaned off all our juices. He then went to his wife and sucked and licked her until she had another orgasm.
They fell asleep, but I laid there for a while and relived the entire evening and wondered where all this was heading.
Am I still a sissy? Or am I something else? What will happen tomorrow?
What do you think?
It was December 15th, the dorm was empty and I was alone in my room.
My parents sent me away to an all-male College/Boarding School in the Northeast, USA. They suspected I was Bi or Gay and wanted me out of sight and out of their way. They informed me I would be in school until the summer break.
My name is Timmy. I am eighteen years old. I am green eyed, five foot ten, one hundred forty pounds, quite skinny, very feminine looking and not well endowed with only a five inch thin cock but I am told I have a great ass. My body has zero hair except on my head which is blond and on the long side. The only area I need to remove hair is on my pubic area and that is very light blond. I love to wear pantyhose and panties because they feel good on my skin and I feel so sexy when I do. I am comfortable as a closet cross-dressing young man. Many have said my face is so pretty I should have been a girl and I agree. That is why when I am servicing someone I call myself Tammy.
That day I was feeling low because all my friends went home for the holidays. I hadn’t had sex for three days and was sitting on my bed and feeling very horny. I had just reached inside my shorts to stroke my boner when my cell rang.
“Hello, Timmy,” Mrs. Longinbeckerstien said. “I hope I am not disturbing you on this crisp Saturday morning.”
Holly shit why is Mrs. L. calling me I wondered? “Hello Mrs. L.”
“Timmy or should I call you Tammy,” Mrs. L. said.
My brain was screaming, “What the fuck is happening?”
“Your silence is speaking volumes Timmy. Don’t be frightened, I know all about you. My husband shares all the videos with me. Oh, I guess you hadn’t realized his office has cameras to record all his adventures. I watch them every time as he pleasures me. Timmy I am not calling to embarrass you but I am calling to ask a favor.”
“Sure anything you want Mrs. L.”
“Call me Vicky and when you talk to my husband call him John.”
“Tonight we are hosting a cocktail party for our closest friends and some work associates. One of my staff has come down with something and can’t help with our guests. Suzy is a tall young thing and we figured Suzy’s maid outfit will fit you quite well. Come over our home at six this evening. I will help you with hair and make-up and get you dressed. Is that alright with you, Tammy?”
Good God is that all right? My cock was hard as a rock as I feverishly jerked off as I stammered, “Yes, Vicky whatever you want.”
“Good then, see you at six,” she said, as she hung up.
I only stroked my girly cock a few more strokes when I erupted all over my belly and hand. I brought my cum drenched hand to my mouth and savored my sweet load.
I couldn’t wait until it was time to leave. I showered, then made sure what little velvety blond hair had sprung up on my pubic area was removed. I used my electric Epilady Hair Remover. It lasts longer and I don’t get those red bumps you get when you shave.
I put on a pair of hip hugger black silk see through panties and over that jeans and a pullover shirt. Grabbed my coat and gloves and headed cross campus to the Dean’s residence.
I was shaking with excitement when I rang the doorbell.
A young woman answered the door. She was wearing a maid outfit. She looked great in a low cut black corset top, French style short skirt, black stockings with garters and high heels.
She told me to enter and follow her. I obeyed like a little puppy dog.
She led me to a room off the kitchen. It was a separate maid’s quarters complete with bedroom, bath and a kitchen.
She told me to sit at the dressing table and wait.
“Hi Timmy or soon to be Tammy,” Vicky said.
I turned to see a really beautiful woman standing at the door. She was a tall redhead with a perfect body. She looked about thirty years old. I thought if I was a woman I would want to be her.
Vicky went to work on me. She applied makeup, lipstick, and a red wig. I must say I looked like a sweet virgin school girl. I wasn’t a virgin anymore, at least with men.
She then helped me with my outfit. It was the same as the maid who let me in at the door. The corset actually made my chest look like I had small breasts. It slimmed my waist even more then my twenty two inches. It also made my hips appear bigger. My legs looked long and beautiful in the shear black stockings and four inch heels. I looked in the full length mirror and saw a really hot girlie boy.
Vicky explained, “You are to serve the guest drinks. You are also to cater to their every need. You have catered to my husband’s needs along with the needs of some professors and most of the rugby team so I am sure you understand what I mean. Do we understand each other?”
“Yes Vicky, I believe I do.”
At that point my little cock sprang to attention pushing up out the top of my panties but was restricted by the tight maid skirt.
The guests arrived on time. I knew some of the professors but no one else. I served drinks for about two hours before things started to heat up. The guests were getting loud. Some were groping each other or even feeling up the other maids.
That is when Mr. L. (John) pulled me to him as he was seated in a big wing back chair. He sat me on his lap and put his hand behind my neck. He then gently guided my face to his. He kissed me tenderly on the lips and then slipped his tongue into my mouth. It was a kiss with passion. A kiss that said more is expected.
As he continued to kiss me I opened my eyes to see Vicky smiling at me. She winked and nodded yes. I closed my eyes and kissed John back.
We broke the kiss. I knew what I wanted. I slide to my knees between John’s legs and began to unzip his pants. I felt the entire room looking at me. A hush fell over the entire party as I pulled John’s thick hard cock free.
I held him in my hand as I admired his manhood. I then bent and kissed the tip of his beautiful cock. Pre-cum was leaking out and I scooped it off with my tongue. He stood and removed his pants and underwear and then his shirt. He was naked before me. I reached around him and held his buttocks firmly as I pulled him to my eager mouth. I engulfed his cock until my nose was touching his pubic hair. He held my head as I started to bob my head up and down on his erect eight inches of hard thick man meat.
I felt him tighten up and knew he was close. I was the star of the show now. I reached between his ass cheeks and placed my finger to his rose bud. That sent him over the edge. I pulled his cock out until just the tip was resting on my tongue. I pushed into his ass and massaged his prostate. He exploded sending a stream of white hot juice to the back of my throat. Then five long ropes of cum landed on my outstretched tongue.
I looked into John’s eyes as I happily swallowed his entire sweet load.
The room burst into cheers and applause.
I feel to the floor on my hands and knees. I raised my ass high in the air and waited.
I didn’t need to wait long. Someone pulled my panties down and off exposing my perfect heart shaped ass. I had reached under and pulled my cock and balls forward so all the guest saw was my ready and willing boy pussy.
Vicky said, “Wait a minute.” She came over and applied gel to my cunt. She expertly pushed some in as she fingered my waiting love tunnel.
The first man of the night lined his hard cock to my opening. He pushed roughly in. His cock was about seven inches long and his thickness was on the average side. He pumped vigorously for several minutes when he announced he was coming. He shot his burning hot load deep into my bowels. Then just as quick he pulled out. I never knew who he was as my face was buried in the carpet.
He was quickly replaced by another. His cock was thicker and longer. I must say it did hurt as he relentlessly pounded with all his might until he also came.
I looked around and saw the same happening to the other maids. What shocked me was all were girlie boys like me. The wives of the guests were watching. Some were taking pictures. Some were making out. Most were in a state of undress.
One of the guests slid under me in a sixty nine position. He kissed and sucked my willing little boner as I took his long hard cock to my mouth. While we were enjoying several other male guests lined up and had a turn in my ass. I was in sissy slut heaven.
The guy I was sucking tasted so good I was lost in passion. My ass was being filled for the sixth time when I couldn’t hold out any longer. The guy I was sucking sensed this and we came at the same time. We each swallowed repeatedly but not before savoring the taste and texture of each other’s cum.
The guests all had a great time. Men enjoyed men and the women enjoyed women.
At about two in the morning the last guest left. The other maids cleaned up but I was asked to come up to the master suite.
Vicky said, “Please sleep with us tonight.”
We undressed and went to the shower together. Vicky and John washed themselves then they washed me. They even toweled me dry before we adjourned to their king sized bed.
I was in the middle. John kissed my nipples as Vicky kissed me on the lips. This was my first real kiss by a woman. It was very nice. We continued to kiss as she ran her hands over my entire body. I likewise felt my first breasts and touched my first pussy.
Vicky moved to her back as she guided me on top of her. John held my little dick in his hand and placed it to the edge of her slit. Oh my God I was going to fuck a woman.
John pushed down on my ass and my ready cock pushed into her folds. It was like pushing my cock into a tub of softened butter, only better.
I moved in and out as she met my every move with her own. We were actually fucking. I kissed her and she kissed me. It felt like we fucked for hours but I’m sure it was only minutes.
I screamed out as I exploded. That set her off as I felt her vagina clamp down around my penis. She actually worked her muscles to force out all my potent seed.
I lay in her arms for a long time as our heart rates slowed. When I rolled off John took my soft penis in his mouth and cleaned off all our juices. He then went to his wife and sucked and licked her until she had another orgasm.
They fell asleep, but I laid there for a while and relived the entire evening and wondered where all this was heading.
Am I still a sissy? Or am I something else? What will happen tomorrow?
What do you think?
Louise
- 09.07.2021
- 25
- 0
- Category:
- Bisexual
