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Sean Obyrne

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Sean Obryne.

A Nice Couple

Author: 

  • New Author
  • Sean Obyrne

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Femdom / Humiliation

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)
A Nice Couple

by Sean Obyrne

 

They were a very nice couple that we had met about a year ago. Mary and

Marty were their names. We would go out socially and for the most part we enjoyed

each others company. We hadn’t been together socially for about six months. I

always thought he was a little strange as he was very quiet and submissive to his

wife but other than that, we had a nice time together. He was very short and thin and

with a smooth complection.

My wife Judy, who has always admitted to being bisexual, started to bug me

about getting together with them for more than just dinner. I have never been with a

man, but I have thought about it and I finally agreed to try it. She told me that Mary

had caught Marty with another woman and he had agreed to do anything to keep

her. She decided to feminize him and made him wear panties at all times, knowing

that he would not let another woman see him wearing them. As soon as he came

home from work she would make him put on a bra, panties and other female clothes

and she had started giving him female hormones. She had made him quit his job and

now he was a full time housewife. He had agreed to us coming over to the house

and he also agreed, to do anything I wanted.

Mary greeted us at the door, she gave Judy a long lingering kiss and then

shook my hand. She led us into the family room and Marty was standing in the

background, completely dressed as a female and was incredibly pretty. He was

wearing a pretty black evening dress and looked very sexy. If I hadn’t known better,

I would have thought he was a normal female. He was acting very shy as Judy

introduced him as Vicki.

We all sat and made small talk for a while. I sat there looking at Vicki. She

was exquisite from head to toe. I reached out and took her hand. Her nails were long

and looked professionally done. "Did you do these yourself?" I asked, as I held her

hand.

"Mary took me to the beauty shop and had them do a complete make over"

she said. "Was that embarrassing?" I asked. "Not too bad at first but then Mary told

them I was really her husband and then I was mortified" she said. I continued to

hold her little hand as we talked. "Was that your most embarrassing moment?" I

asked. "No the worst time was when this first started. She took me to the

department store, lingerie department, dressed as a man and told the girls I wanted

to pick out some panties for myself and had them measure me, and then watch as I

picked out a couple dozen pairs of panties and a few training bras. She had

instructed me ahead of time that I was to chose mostly pink and white panties and

most of them had to be lacy and sexy. I was humiliated but I did it. She then invited

her mother over to help dress me. I objected and her mother grabbed me and pulled

down my pants and spanked me. Needless to say I was very embarrassing. She then

picked out the sexiest pink panties and a training bra and dressed me in them and

that was probably the worst time" she said. Her mother stayed the rest of the day

and I was instructed to clean the house. I was very embarrassed working around the

house, wearing just my training bra, pink panties and a filmy little apron.

"Do you still wear a training bra" I asked? "No she replied I wear a full A_

cup and will have to soon switch to a B_cup" she said. She blushed as I told her I

couldn’t wait to see them. I reached out and caressed one of her breasts. "Do you

like wearing panties" I asked. "I love them and I look forward to dressing every

day" she said.

Mary put on some soft music. The girls got up to dance so I asked Vicki to

dance and she reluctantly agreed and got up and I took her in my arms. I pulled her

close and whispered in her ear. "Are you sure you are all right with this?" I asked.

"Yes, just go slow and I will be all right" she said. She looked and smelled

wonderful. "What is that perfume you are wearing?" I asked as I pulled her close

and nuzzled her neck. She told me it was obsession. I cupped the cheeks of her

pantied ass as we danced. I could feel her dick get hard and pressing against me as

we danced. I was getting excited also. She looked up at me and I gently kissed her.

She blushed and returned the kiss and at that moment, I knew I was going to enjoy

this evening. I looked over at the girls and they were lost in each others arms and

their hands were all over each other. The music stopped and Vicki and I went and

got another drink we sat and talked. I lit a joint and we both became incredibly

buzzed. I made her move over and sit on my lap. I held her in my arms and my

hands roved over her sexy body and her little tittles. I reached into her panties and

massaged her panty covered penis as I kissed her. She was so submissive and

spread open he legs and let me fondle her as I kissed her soft lips. The girls had

already retired for the evening and I suggested that Vicki go slip into something

more comfortable.

She returned about 10 minutes later wearing a short pink sexy night gown

with a matching peignoir. I knew at that moment that, in spite of my reservations

about being with a man, this was going to be an evening to remember. I took her

hand and led her into the bedroom. The room was dimly lit with candles and as I

stood there with my back to the bed I kissed her again. She took off the peignoir and

hung it in the closet. She looked wonderful, in the pretty pink gown. I asked her

again if she was all right and she indicated that she would be fine.

"Undress me slowly, hon" I told her. She seemed startled that I would

request that. She was obviously very embarrassed as she started to unbutton my

shirt. I gently caressed her little tittles as she worked and her nipples got hard as I

gently pinched them. I kissed her again. My hands strayed down to her panty

covered, rock hard penis and I gently caressed it as she undressed me.

She got my shirt off, and I made her suck on my little tittles, first the right one

and then the left, this made me very horney. She moved her hands to my belt and,

after opening it she unzipped my pants and she had to kneel down to pull them

down. She hesitated as I stood there, wearing nothing but my tight white jockey

shorts. My dick was tenting the front of my briefs and was I so excited that my dick

was jumping up and down. "Pull my undies off honey" I said and she slowly did so,

allowing my hard dick to spring into view. I sat down on the bed and then lay back

and she had not moved from her kneeling position. She was obviously very

embarrassed to be this near a naked man. "Have you ever touched another mans

dick?" I asked her, as I reached out and took her hands. She told me that she had

never been around another man, much less touched one.

"I want you to slowly touch every inch of my dick and balls" I told her as I

placed her hands on my crotch. I watched her as she moved her hands slowly over

my six inch_circumcised dick and then cupped my balls. I was in heaven. "Kiss it

baby" I said. She reluctantly lowered her face to my crotch and kissed the head of

my dick. "Kiss my balls sweetheart" I said as I moved my legs as far apart as I

could and exposed my butt crack. Her tongue roved all over my crotch. "Lick under

my balls" I said and then I felt her licking my behind. Wow this was heaven, I never

thought she would go this far. Her hands continued to play with my dick and balls as

she licked and then I felt her tongue entering my behind. She seemed to be enjoying

what she was doing but I had to stop her in spite of the pleasure I was receiving as I

was about to come and I wanted this evening to last a long time.

"I kissed her and pulled her into the bed. "Lets pull your pretty pink panties

down" I said as I slowly lowered them. Her dick and balls sprang into view framed

by the straps from her garter belt and nylons. Her penis was about as big as mine

and was circumcised. "You shaved" I exclaimed as I looked at her. I was glad as I

don’t think I could have continued with a hairy man.

I sat there just looking at her near naked body and started to imagine what I

was going to do next. Her dick was jumping around with excitement. I have never

touched another mans penis and I told her so as I slowly felt and inspected her six

inch dick and large balls. The skin was soft and velvety. She was hard as a rock and

so was I as my hands slowly roved over her shaved dick and balls. I was very

embarrassed to touch her in such an intimate way but also very excited. As I fondled

her dick with one hand my other hand moved to her ass and I slowly inserted a

finger in her behind. She wiggled around with excitement and pushed against my

hand to drive my finger deeper.

I took her cock in my hand again and felt its hardness, sliding my fingers

slowly and gently around it. I wanted her cock wet so I could really drive her crazy

so I moved round so that my head was near her cock and I gently kissed her

stomach and thighs, moving closer to her cock which looked so hard and horny. At

that moment all I wanted to do was take it in my mouth, but instead I took her in my

hand and moved my mouth down and slowly licked and sucked her balls, while

gently rubbing her with my hand. Her groans were driving me wild. I moved my

tongue slowly up the shaft of her cock until I reached the head. My hands roved

over her nylon covered legs and she moaned with excitement.

Gently holding her in my hand I flicked my tongue round the head of her

cock, running it gently under the ridge of the head and up onto the wet eye. I took

her slowly for the first time into the warmth of my mouth and I gently, hungrily ran

my hot tongue over her cock head, drawing her deeper and deeper into the heat of

my mouth. She started to move very slowly in my mouth while my hand squeezed

and caressed her balls. She was sucking my dick with incredible passion and I knew

I would come soon. I could feel her rigid cock swell in my mouth as I started to lose

control. She moved faster and faster in my mouth and I felt her coming up from

inside her like a wave, an orgasm which shook her whole body as she moaned my

name. I came at the same time she did and it was the most wonderful feeling ever.

My mouth is filled with her hot cum as her body writhed in ecstasy. I hungrily

drank, swallowed and licked her come, not wanted to miss a drop of my lover’s

orgasm. I was so hot I didn't know what to do but Vicki hadn't finished. She moved

back to my crotch and took my hard dick in her mouth and proceeded to drive me

crazy. She licked and sucked as I felt her long finger enter my behind.

We stopped and rested for a while. "I’m going to fuck you" I said as I took

the tube of KY jelly that was next to the bed and started to lube her behind. "Oh

honey I am scared that you are going to hurt me" she said. "I’ll go slow" I said, as I

moved her around and into position. She swung her smooth, shapely legs over my

shoulders, and exposed her puckered ass to my view. I had the pleasure of touching

it thoroughly in one of our past encounters, and now she was offering it up to

penetration by my dick. I couldn't have been more excited. Her little bird was

standing at its full ridged length, and she moved her hand to stroke it while I

penetrated her anus.

Mere words cannot describe my joy as the head of my cock squeezed through

her tightly clenched opening. There was a momentary look of great pain on her

part, and I hesitated, but then it subsided, and I continued my slow exploration of

her hole. Once I was all the way in, I began a slow, rhythmic pumping that seemed

very natural, and as the event went on and friction permitted, I gradually increased

the rate. Soon I was pumping furiously and Vicki was moaning in time. Suddenly, I

spontaneously joined her, and immediately felt myself ejaculating. I had never

pulled out of her mouth during blow jobs, and so saw no reason to pull myself out

now. Instead, I shot my entire load into her precious ass. She climaxed at about

this same time, as I could feel the rhythmic contractions of her ass muscles around

the base of my cock. Her own spasms helped to drain me dry, and so I pulled out,

and laid my softening penis on top of hers. She lay there contentedly, fondling me

with one hand, herself with the other. A smile of contentment radiated from her

face.

We rested a while and then went into the bathroom and enjoyed a long

soaking bath together. I gently washed her sexy body and she returned the favor.

We dried each other and we went back to the bedroom and she slipped on some

pretty panties and a gown and then picked out a pair of pink satin nylon briefs and

held them for me to step into. I did so immediately and she pulled them up my legs

and arranged them around my waist. She then went to the closet and came back with

a beautiful pink floor length gown and dressed me in it. We lay together touching

each other then we fell asleep in each others arms.

 

Anybody that would like to rewrite this story of just copy the idea, please do so with

my blessing.

Sean

My Natalie

Author: 

  • Sean Obyrne

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

TG Elements: 

  • Sissies

Permission: 

  • Posted by author(s)

My Natalie

by Sean Obyrne

Anybody that would like to rewrite this story of just copy the idea, please do so with my blessing.

Sean

My Natalie

The day had finally arrived. I was sitting in the airport waiting for her plane to arrive. I had another hour to wait. I was so afraid of something going wrong I went to the airport two hours early. There was no way I was going to miss this flight. She was coming to me at last.

Let me think about how this all started. I met her in a chat room and somehow we just clicked. The wonderful fantasies we played out were so fun and exciting, I would rush to my computer every morning, hoping she would be there. She had given me her email address but I had lost it and kept forgetting to ask her to give it to me again. We were so comfortable with each other I thought it would last forever, but one day she was gone. I kept looking for her, my cute little gay boy. Yes I knew she was really a man but she was everything I ever wanted, and I wanted her to be my full time sissy boy. Her nick name was Natalie. Every time I saw a Natalie my heart raced, but I never found her. Then one day there she was, my wonderful Paul. It was so wonderful to have her back. We exchanged email addresses and continued to chat, finally she decided to come to me. I sent her the plane ticket and here I sit waiting.

I have fixed up a room in my house for her, all feminine and pretty. She sent me her clothing sizes and I have bought her and extensive ward robe. I can hardly wait for her to see it and to see her wearing them.

Oh wonderful the plane is here. They are coming down the ramp. There he is, my Paul. He had sent me a picture and I recognized him immediately. I wanted to kiss him so much but could not do that the way he was dressed. I shook his hand and hugged him and we went to get the luggage.

Riding in the car on the way to my house, our conversation was strained to say the least. We both knew how happy we were but some things just went unspoken. I finally reached over and touched his arm and said "here we are honey". He smiled at me and told me what a nice house I had. I pulled into the garage and closed the door. Then I took him in my arms and kissed his soft pretty lips. "Oh god I am so happy to have you here with me, I have waited so long, come here you little faggot" he smiled at me and said shut up and kiss me again. Finally I reluctantly released him from my arms and said we had better get the bags into the house.

We each took one and I led her to her new room. "Well here it is honey, I hope you like it." We entered the pink frilly room and I could see her just light up with pleasure. She turned to me and gave me a wonderful long kiss.

"I’m sure you want to take a nice bath and change, I will be in the living room". I kissed her again and slowly left. I took a quick shower and slipped into my satin pajamas and went to the living room to wait for you.

Finally after almost two hours, You entered the room. You are so beautiful I am stunned. Your hair is beautiful, your makeup is perfect and you are wearing a beautiful pink silky night gown and robe. "Oh god honey you look wonderful" holding my arms out to you. I watch enthraled as you walk over to me and settle into my arms.

Oh god honey it is so wonderful to hold you in my arms at last. My plan was to slowly get to know you. Touching and chatting for a while, however once I had you so near, I could not wait. I stood up with you in my arms and carried you to my bed. Kissing you as I carried you. The beautiful smile on your face was all the approval I needed.

I helped you remove your robe and we lay together in the bed. You are so beautiful in your pretty nightie.

"Oh god honey I cant believe you are here with me, I have waited so long for this moment". Dimming the lights we move into each others arms and just hold each other. I felt your hardness pressing against me and I moved my hand to it and gently squeezed it through your sheer little panties.

Neighbor

Author: 

  • New Author
  • Sean Obyrne

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Caught with Consequences

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)
Neighbor

by SEAN OBYRNE

It had been six months since my wife died. I had been devastated, at her loss, but life must go on. I finally started to circulate and go to some community events. The church I attended had a picnic and I was lonely so I went. The entire event was rather boring and I walked around looking at the various booths. Then I saw the young boy who owned the house next to me. We had chatted a few times and he had told me that his parents had been killed in a plane crash last year and he now owned the house and lived there alone. Bobby was playing gin rummy at the card booth and I stopped and watched the game. He happened to look up and see me and his face turned into a great big smile. I sat and watched until he was done.

"Hey Bobby you are a real good player. We should get together at my house and play sometime ". I said as we walked over to the drink tent and got a coke. He said he would love to come over and play. We parted with the understanding that we would get together Friday night.

He came over Friday and I ordered a pizza as I’m not a good cook. We were having a great time playing cards and eating pizza, when he offered to go get a couple more beers out of the fridge. He hopped up and slipped on the throw rug, slipped and sprained his ankle. I helped him to the sofa and before he could stop me I pulled off his shoe and sock, so I could massage his ankle. As I started to massage it I could see that he was wearing sheer nylon stockings and his toe nails were painted pink.

He hung his head in shame but instead of saying anything I continued to massage his foot.

"I suppose I should get going, Jim " he said as he started to get up.

"Nah sit and relax " I said as I slipped off his other shoe and sock, and slowly started massaging his other foot. "Is the ankle better "? I asked as I looked at him smiling and continued to rub his cute little feet. I was really getting turned on touching his feet and I could see that he was too. My hands slowly moved up his nylon covered hairless legs.

Bobby pulled away and sat up, looking at me he said. "I’m very embarrassed that you have found out my secret, and I guess you want me to leave ".

"No hon I want you to stay and I want to show you something ". With that I stood up and unzipped my pants and let them fall to the ground. I stood there wearing my pretty pink panties as Bobby looked at me.

Anybody that would like to rewrite this story of just copy the idea, please do so with my blessing.

Sean

Runaway

Author: 

  • Sean Obyrne

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Sweet / Sentimental

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)

Runaway

by Sean Obyrne

Anybody that would like to rewrite this story of just copy the idea, please do so with my blessing.

Sean

It was raining steady and very chilly. I was standing by the side of the road hitch hiking. I was chilled through and through and starting to get desperate, when he stopped. I ran and hopped in.

Thanks mister I really appreciate this. He asked how far I was going and I told him 200 miles. He told me his turnoff was about 10 miles ahead. I sat there shivering, grateful for the ride.

We chatted and he inquired about my age. I told him I was 18 although I am only 17. I lied about the reason for my trip. The truth was I was running away from home. My stepmother had searched my room and found the panties I had stolen from her and my collection of transvestite magazines. She told me she was going to tell my father and I knew he would kill me. So I grabbed what little money I had and left, and I have been on the road for two days now.

I was shivering uncontrollably when he told me his turn off was a mile ahead. He suggested that I stay the night at his house and go on in the morning. He said he had plenty of room as he was a widower who’s wife and daughter had been killed a year ago in a head on collision. I agreed immediately as the thought of standing in the rain all night was not pleasant.

When we entered the house, he suggested that the fastest way for me to warm up was a hot bath. He led me into the bathroom and started running the bath. I was so cold I could not open the buttons on my shirt. So after asking my permission, he undressed me. It felt wonderful to be waited on and he seemed to enjoy helping me. I do get embarrassed easy as I am a little over weight and have chubby little titties and a big butt. I did notice him looking at me strange as I got in the tub. He said he would put my clothes in the wash and took them and left.

The bath felt wonderful. I was finally getting warm. I love baths, Daddy used to bathe me up until he married the bitch. She said it was sick and made him stop. I really did like him washing me every night and he seemed to really love doing it. When we were done he would take his time drying me and then he would dress me in my jammies and put me to bed with a big kiss. I miss those times most of all.

At this point Joe came back into the room and sat down and started talking with me. He handed my the shampoo and suggested that I wash my pretty hair. Something about the way he was looking and acting made me offer to let him do it. Wow did his face light up as he came over and gently shampooed my hair. He took his time as I lay there enjoying the attention. It brought back many fond memories. Joe stopped all of a sudden after he had rinsed my hair three times and turned away as if he were embarrassed. I got out and started to dry myself as he turned his back, I tried to hide my little dicky as it was hard for some reason but I could see him watching me in the mirror.

I inquired about my clothes and he explained that they were in the wash and would be done in the morning. He suggested that I wear some of his late daughters clothes as she was about my size. He led me to her room and told me to find what I needed.

After he left I went over and opened the top drawer and it was almost full of neatly folded and stacked panties. At first I thought I should wear a plain white cotton pair, but then I noticed a lovely pink silky nylon pair with extra lace on them and I knew I had to try them on. They felt delicious and looked wonderful. Next I found some lovely pink nylon lounging pajamas and slipped them on. I was in heaven. I sat in front of the mirror and used the hair dryer until I was dry and silky. Looking in the mirror I had to admit that I looked really cute. Then I ventured out into the house.

Joe was sitting on the sofa and he seemed to beam as I entered the room. He patted the seat next to him so I went over and sat down next to him. He was a little drunk by this point and he put his arm around my and kissed me. I started to cry.

Oh I am so sorry he said as he hastily removed his arm. Its just that I have been so lonely and you look so much like my daughter.

Its not that I told him, its just that at this moment I am so happy but tomorrow you will want me to leave.

He hugged me and told me I could stay as long as I wanted. I just snuggled in his arms. He cuddled me and gently touched my little breasts as he talked to me. I was so happy I loved him to hold me and cuddle with me the way daddy used to do. Some times daddy would hold me for hours and he liked to touch me too. I miss that so much. She ruined everything when she moved in.

I was so tired from the limited amount of sleep the last few days, that I feel asleep in Joe’s arms. I woke in the morning and I was in Joe’s bed. He was behind me with his arms around my and holding me close to him. I could feel his hard penis pressed against me and it was obvious that he was naked. I don’t know why but I felt so safe and secure in his arms. I was still wearing my silky panties and my pretty pajamas and they felt so wonderful on my skin. I was so happy I just lay there in the comfort of his arms until he started to wake. I gave no indication that I was awake and I felt him kiss my neck, before he got up.

After a few minutes I could smell coffee brewing and I was famished so I got up and went into Beth’s room and found a pretty pink robe and some fuzzy slippers. Then I went into the kitchen. Joe was dressed in his robe and reading the paper as I entered. I could just see his face light up as he saw me.

Hi Joe, I said as I smiled at him. I’m sorry I feel asleep on you last night. Hope I wasn’t too much trouble.

He had a big smile on his face as he assured me that I was no trouble at all. He said he loved taking care of me and helping me to bed. He said he did not want me to wake up alone and scared so he put me in his bed. I thanked him for being so nice. For some reason he seemed embarrassed and he turned away and offered to make breakfast. I was famished, after not having anything to eat in last 24 hours. He made a big meal of bacon and scrambled eggs and we had a wonderful time eating and chatting.

I have to ask Joe, did you mean it when you said I could stay awhile, I really wont be any trouble and I am a good house keeper and would be glad to take care of the house for you.

You have the job honey for as long as you want. Joe said. I walked over and kissed him and thanked him for his help. He seemed so surprised for a moment and then he kissed me back. He hugged me tight and I could feel his hardness pressing into me. My daddy used to get that way too and it brought back those fond memories.

Joe said he was going to take a bath and asked if I would join him. Wow what do you think I said. We went into the master bath and he started to fill the big Jacuzzi tub. Joe took off his robe and got into the tub. I started to undress and when I was down to just my panties he asked me to stop and show them to him. Boy was that embarrassing but I liked pleasing him. I slowly turned so he could see me from all angles. Then I took them off and got in the tub.

I sat across from him and told him about what daddy and I used to do. He had such a big smile as he told me he would love to be my new daddy if I would let him. I moved over next to him and threw my arms around his neck and kissed him. Our naked bodies pressed against each other. He wanted to wash me and I handed him the soap. Slowly and gently he washed my body and then asked me to stand so he could reach the rest of me. I happily did so and he gently washed the rest of me, paying close attention to my penis and my behind. I was so hard when he touched me. He seemed to like my hairless body and my little titties. He then shampooed my hair and spent more time on it than he had done yesterday. It was so relaxing yet so erotic. Then he asked me to wash him. He was strong and muscular with very little body hair. I really enjoyed washing him and when I got to his crotch he was hard as a rock. I have never touched anyone down there and I really got excited doing it. Suddenly he stopped me and said that is enough for now.

Ok daddy I said as I got out of the tub. Turning my back to him I got out of the tub and started drying myself. He just sat there and watched me. I wrapped my hair in a towel, looked at him and smiled and said I was going to get dressed. I gathered up my dirty clothes and went into Beth’s room. Looking through the dresser drawer I found a cute little garter belt and stockings and put them on. In the panty drawer I found some lovely little white nylon panties with pink trim. They felt so nice. Beth’s bras fit me perfectly and made my chubby little breasts look so much better. Then I got a pretty little summer dress out of the closet and slipped it on. Put my hair in a pony tail and put on a little lip stick. A spritz of perfume. Looked in the mirror, that will have to do I thought to myself. I felt so pretty and was hoping daddy would approve, slipping on some low heel shoes, I went out to find daddy.

Hi daddy. He was sitting in the living room reading the paper. I could tell he liked the way I looked as he just beamed at me. I walked over and kissed him and thanked him for letting me stay. Do I please u daddy, spinning around so he could see me.

I’m going to get the house work done daddy.

Sweetie

Author: 

  • New Author
  • Sean Obyrne

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Femdom / Humiliation

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)

Sweetie

by Sean Obyrne

Finally the day has come. Here I sit at the airport waiting for his plane. The

long wait is almost over. We met in a chat room and after months of correspondence

and phone calls finally he has decided to come to me. He is everything I have ever

wanted. Yes I know all the arguments he is a mere 18 and I am 40. Some people

will think my desires are aberrant, but I don’t care. I want him and I want him now,

and amazingly he wants me.

At first we exchanged pictures and although he told me he was 18, he looked

14. He was short and a little chubby. I fell in love with his photos but insisted that

he send me proof of age, which he did. He was a very unhappy child who’s mother

had died when he was young and his father was a drunk who did not like him

because he was chubby, and Dad thought he should be the macho asshole that he

never was. Dad gave all his attention to his sister, instead of showing some

affection to his chubby son. He would have been happy just to have his father spank

him but even that never happened.

My sweetie even tried on some of his dead mothers panties and other clothes

in the hope that this would satisfy the vacancy in his life, but nothing seemed to

help. He lived in a fantasy land where he would be turned into a female and Daddy

would love him. It was so sad to hear his story. I vowed that I would fill the void in

his life. The guilt he felt from wearing her undies, was washed away by the fantasies

that he experienced while being dressed.

Now here I sit with an hour untill his arrival time, just waiting for him and

thinking about how I hoped our life would become. I had come to the airport early

as I did not want to miss his plane. Finally here is the plane, pulling up to the gate.

God this is so exciting. The anticipation, the longing. The need, soon I will have

him.

The people are getting off the plane, yes there he is. He looks so young and

cute, he sees me and gives me a big smile. I hug him, I would love to kiss him but

that will have to wait. We head for the car, I know he has no luggage as I have

instructed him to only bring his personal things. Traffic is light this time of day and

soon I am pulling into my garage. The door closes behind us and I take him into my

arms and kiss his soft lips.

We enter the house and sit and chat. Come stand in front of me. You slowly

walk over to where I am seated. Brace yourself on my shoulder sweetie and raise

your foot. I slowly remove your male shoe and sock. I see that your have followed

instructions and are wearing shear stockings. Now the other foot sweetie. Removing

your shoe and sock and massaging your foot, your toenails are painted the prettiest

shade of pink. I slowly let go of your foot and you stand in front of me again. I reach

forward and undo your belt and open your fly and your pants drop to the floor. Oh

god your garter belt and pink panties are so pretty. I can see how excited you are

and I am so pleased. I gently touch you and you moan. This is so wonderful, just as

I imagined it would be. Now lets get your sweater off. Oh yes, your camisole and

bra are so pretty. Soft and silky and so lacy. Touching your bra I can feel your hard

little nipples.

Sit on my lap sweetie. Your hair is tied up in a pony tail and I undo the rubber

band holding it and then taking a hair brush, I slowly brush out your pretty blonde

hair. Holding you close as I brush, I can smell just a hint of perfume. Our lips meet

in a long passionate kiss as my hands explore your lovely body. I lay you back on

the couch and then start to explore your pretty body with my hands and lips. Kissing

and touching your ears, your eyes, your pretty neck, I just can’t seem to get enough

of my sweetie. You moan and beg me to make love to you. My hand and lips move

lower on your soft body, until I am kissing and touching your hard nipples. I am so

hard in my pants but for now I just want to please you. Raising your camisole I kiss

your soft little belly, my hands moving to your nyloned legs. Slowly I lower your

pretty panties and your little penis pops out. I am so pleased that you shaved

everywhere, as I instructed you to do. My hand slowly explores your pretty bottom

as my lips move to your little four inch cut penis. Slowly I suction it into my mouth

as I push a finger into your tight little bottom. My other hand caressing your little

balls. You taste so wonderful and you are so hard. I can hear my sweetie screaming

as I slowly suck her. I feel your hands on my head pulling me closer to you. Yes, I

feel you coming. I taste you. So wonderful. Swallowing every drop. Now you are

really mine.

To be continued.

Anybody that would like to rewrite this story of just copy the idea, please do so with

my blessing.

Sean

Victor

Author: 

  • Sean Obyrne

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Caught with Consequences

TG Elements: 

  • Dominance & Submission / Bondage

Permission: 

  • Posted by author(s)

Victor

by Sean Obyrne

Anybody that would like to rewrite this story of just copy the idea, please do so with

my blessing.

Sean

  

  

My name is John and I am the new kid in town, as Dad was transferred again

and I had no choice in the matter. It was the forth move in my short 14 years. It was

the first day in school and after going through the lunch line, I was looking for a

place to sit. I spotted a table with only one boy sitting at it. He was a nice looking

boy with blond hair and was a little chubby and he looked lonely.

"Hi. Do you mind if I sit here"?

"Please do" he said with a smile.

I reached out and shook his hand. "I’m John and I’m new in town" I said.

I was surprised at how soft his hand was and how weak his grip. I kept trying

to make conversation as I ate. When I told him where I lived, he really brightened

up and told me he lived two doors down from me. He then warned me that the other

kids in school, might give me a hard time if I was nice to the fat boy. He looked so

sad when he said it, that I decided we were gonna be real good friends. We sat

together at lunch the rest of the week and Friday he invited me over to hang out,

after school. He told me that he lived with just he mother as his Dad had been killed

in the last war.

I knocked on his door and his Mom let me in. She was chubby also but very

nice looking. She told me to go up to Vic’s room as he was probably on his

computer. Vic had told me that his mom had a heart condition and never went

upstairs. I walked up the stairs and went into Vic’s room. He was sitting at his

computer and hastily dumped out of what he was looking at as I entered the room.

"You are early." he said.

"Hi Vic", I said as I entered the room. "What are you looking at"?

"Hi, just junk" he said, as he looked at me sheepishly. I noticed that he was a

little turned on, from the budge in his pants, that he was trying to hide. "Nice room

dude." I said as I looked around and gave him time to cool off. "That’s a nice

computer, how long have you had it?" We chatted a little and he told me he was

hooked up to the internet by cable. "Why don’t you get us some cokes and then you

can show me some of your favorite sites?"

He bounded out of the room and as soon as he was gone I went over and

clicked on his bookmarks. Wow, yes there they were, Fictionmania, Crystals story

site, Best of Nifty, Panty Lovers International, Sissy Land, Mrs_Silk plus many

more. Yes, this is what I had hoped for, now I knew he was a sissy. Soon he would

be my sissy. I went back to the home page and waited for him to come back.

"Mom sent up some sandwiches too," he said as he walked in carrying a tray.

A big smile on his face. He sure is a cutie, I thought to myself as I accepted the

sandwich and coke. We chilled and ate our snack and just had a nice time talking.

"Now show me some of the sites you like to visit." He sat in front of the

computer and I stood directly behind him, with my hands on his shoulders, as he

brought up some mild porn sites. "Wow, I never get to see any of these as my Dad

blocked a lot of this stuff, show me more." I was lying about them being blocked on

my computer, but I wanted him to show my what he really liked. I gently massaged

his shoulders and I could feel my dick getting hard, standing so close to him, I knew

he was aware of my hard on as I poked him a few times.

Now, really show me some of the sites you like to spend time at hon. He

made no attempt to move away from me and he went to Fictionmania. Then he

leaned back against my body and raised his head to look back at me. I smiled at him

and then leaned down and kissed his soft lips. The kiss lasted maybe a minute and

then he moved back to the computer. I continued to stand behind him and I reached

down and unbuttoned his shirt. He made no attempt to stop me and then I reached

down and cupped his chubby little titties. They were quite large and felt so soft and

nice. Gently pinching his hard nipples. I continued to fondle him as I bent down and

whispered in his ear. "Do you want me to stop hon?"

He hesitated for a second and then whispered —"NO."

I kissed his ear and whispered into it. "Trade places with me honey". He

stood up slowly and I sat in the chair and then slowly finished unbuttoning his shirt

and slipped it off him. His titties were so lovely to look at and his nipples were so

hard. I continued to fondle them as I looked at him, "You need to wear a bra hon."

He looked so embarrassed and yet was so excited.

I pulled him close and gently sucked on his hard nipple as I slipped my hand

into his pants and gently squeezed his hard little penis. His moans were getting

louder and louder so I covered his lips with mine as I opened his pants and let them

fall to the floor. He was standing there, wearing just his tight white jockies and they

were so tented. I slowly traced his hard little penis with my fingers and It was

jumping around in his undies. Again I asked him if he wanted me to stop, and again

he said no. Taking the waist band in my hands I slowly slipped his little cotton

undies down, and his little penis jumped out at me. It was less than four inches long,

circumcised and not very thick, and was completely hairless.

I reached out and pulled him to me and kissed his little penis and then

cupping his chubby behind, I pulled him closer to me, hugged him close and kissed

him again. I led him over to the bed and he lay on his belly with his with his cute ass

sticking up in the air. Sitting next to him.

"Maybe we should slow down a little and think about this hon." I said as I gently

started massaging his soft body.

He just moaned and let me do what I wanted.

His chubby body was so appealing I just had to touch it. Tell me about

yourself honey I said as I slowly explored his body with my hands.

He told me about how miserable he had been to grow up without a father and

how the kids had teased him because he was so chubby. My hands wandered over

his soft silky body as he talked and I found my hands exploring his chubby behind.

His skin was so soft and his behind was so cute. My fingers slipped into the crack

and he spread his legs farther apart. I found his little pucker and slowly pushed my

finger into him. He moaned and pushed back at my finger and It sank deep into him. I

bent down and started nursing on his cute tittie as I move my finger in and out. I was

about to insert a second finger, when I heard his mother calling him. He jumped up

and started dressing. I went to see what she wanted and she told me dinner we ready

and I was invited to stay and eat. She also suggested that I sleep over as their was

no school tomorrow. I called mom and she readily gave her consent.

Anybody that would like to rewrite this story of just copy the idea, please do so with

my blessing.

Sean

room for rent

Author: 

  • New Author
  • Sean Obyrne

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Femdom / Humiliation

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)

Room for Rent

by Sean Obyrne

Anybody that would like to rewrite this story or just copy the idea, please do so with my blessing. --Sean

I saw the ad in the paper. (Room for rent), and as I was new in town and looking for work it seemed perfect, so I called the number. Mrs. Elliott answered the phone and invited me over to discuss it.

I finally found her big two story house and knocked. Mrs. Elliott answered the door. She was beautiful. She smiled and invited me in.

She showed the room to me and told me, I would be sharing it with her 18 year old son and I thought it would be perfect as I am only twenty.

The room had two double beds and an adjoining bathroom. The price she quoted for the room was about half of what she could have rented it for, but who am I to argue.

We sat and chatted for a while and she made us a strong drink. Then she said she wanted to tell me something before I committed myself to the room.

She then moved closer to me and started to tell me about her son Joe. He is a closet sissy and he is very lonely and unhappy and that she was hoping I would draw him out of his shell. She told me that she knew he is taking and wearing her panties and nighties when she was not home but that he was unaware that she knew about it. I was really tenting my pants as she told me about it and she reached down and fondled me. We spent the rest of the day in her bed. She was absolutely wild.

I went to my hotel to pick up my suitcases, knowing my mission was clear. I was to bring out the sissy in Joe Elliott and gently guide him into happiness.

When I returned to the house Joe was there, in fact he helped me get my stuff to the room. He was a very good looking young man. Short and a little chubby but very neatly dressed. He sat on his bed and we chatted as I unpacked. It was late when I got squared away and I told Joe I was going to shower and go to bed. I undressed and went into the shower and I could feel his eyes on me.

"I sleep in the nude joe will that bother you?"

He assured me it would not bother him, so I finished drying my body and then slipped into bed. In the middle of the night I had to go potty and when I returned to bed I made sure the covers would not be hiding my body.

I woke with my usual morning wood and was just laying there pretending to be asleep when mom called us to breakfast. I hopped up and dressed in a hurry and Joe and I went to breakfast. Mom looked wonderful, she was wearing a pretty nightie and matching robe. I sure wanted to get some more of that.

Joe and I sat around and talked and since it was Saturday we decided to go clubbing that evening. We got to the bar and I asked Joe what he wanted and he told me he does not drink, so I ordered him a long island ice tea. Needless to say after a couple of them he was totaled. I managed to get him home and up to our room. He sprawled on the bed fully clothed as I undressed. It became apparent that I would have to undress him or he would sleep in his clothes. I sat on the edge of the bed, naked and slowly removed his shoes and socks. I massaged his feet and toes in an attempt to get him to wake. No luck, I slowly unbuttoned his shirt and my hands touched his little nipples as I removed the shirt. He moaned but still did not wake, at least I did not think he was awake. I gently pinched one of his chubby little titties as I fondled the other one and he continued to act as if he were asleep but I could see his penis was hard. His nipples hardened and I bent down and nursed on one for a few minutes. He had nice little titties, at least an A cup, I made a mental note that we would have to get him some bras.

Time to take off his pants. I opening the belt and pulled down the zipper, and slowly pulled them off, I noticed he was tenting his tight white jockies. I reached up and pulled them down, making sure my hand felt his hard penis as I did it. I sat there looking at him sleeping and gazing at his 4 inch cut penis. Giving it a squeeze, I started covering him and he started to cry.

He told me how lonely his life had been and how lonely he was and asked me to keep him company in his bed. I spooned in behind him and put my arms around him. My hand moved to his hard little penis and I slowly fondled it as he talked to me. My other hand was gently squeezing and touching his hard little nipples. He told me how happy he was to be with me. I kissed his neck as I touched him and my 8 inch cut cock pressed into his cute little ass crack.

I reached over to the night stand and got the tube of lube I had placed there. He spread his legs and I slowly lubed his tight behind. I rolled him over on his back and moved over him. As I bent down to kiss him I slowly started to press into him. He moaned and I stopped and he begged me to keep going. I did not want to hurt him so I went as slow as I could until I was deep inside him. I slowly fucked him as I kissed his lips and sucked on his chubby little boy titties. Finally we had a mutual climax. I collapsed exhausted and held him tight.

Needless to say we did not get much sleep that night. We awoke when mom called us to breakfast. He was cuddled in my arms. He seemed like a new person as we chatted at the breakfast table. He had to hurry off to work and mom and I sat around and discussed what happened.

We both were turned on so much that nothing got done that day. She showed me some pretty clothes she had purchased for Joe but never had the nerve to give him. Panties, nighties, robes and more.

Joe returned from work and we had a nice dinner. Later in the evening when mom was out of ear shot I told him to get ready for bed and that I had put a nice present on the bed for him, and I wanted him to wear it tonight. He went to the room and saw the pretty pink nightie and silky pink panties I had put out for him. I also had put the matching robe and slippers on the chair where he could see them. When I went to bed an hour later he was dressed in his pretties and waiting for me.

The next morning, instead of mom calling us to breakfast, she just barged into the room with coffee. She saw us in bed together with Joe dressed in his pretty nightie and me spooned up against him, holding him in my arms. She told us breakfast was getting cold and put Joe’s robe and slippers on the bed and said to hurry down. Joe was so humiliated that his mother had seen what he was wearing and that she knew he was gay. I then told him she had arranged the entire thing. He was mortified that she knew, but it also excited him beyond belief. I helped him put on the robe and then after jumping into my pajamas I led her down to breakfast.

To be continued

 


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