Neighbours suprise Ch. 03

Story Info
Taking the next step.
2k words
4.7
11.7k
18
Story does not have any tags

Part 3 of the 6 part series

Updated 09/12/2023
Created 10/06/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Delia365
Delia365
165 Followers

I was walking home and passed Jim's house, he was in his front garden, sweeping his path. I stopped and said hello, Jim smiled and walked towards me. I asked if he would like a bit of company later, and got a very excited yes from him.

I told Jim that i would visit him in an hour and carried on home. In my mind i had decided to show Jim how i looked fully made up, makeup, clothes and heels.

I got home and went to my sister's room to look through her makeup. She had so much to choose from, I've put on her makeup many times and knew the items i wanted. I picked out what i needed, careful not to disturb things too much.

I showered and used my mother's soap, it smelt of lavender. I dried myself and used her moisturiser, i knew that it would make my skin feel soft and smell nice. I dressed in my normal clothes and gathered up the makeup, and headed back to Jim's house.

I knocked on his door and he very quickly answered. He showed me through to the living room, on the coffee table there was a bottle of wine and a couple of glasses. I smiled and asked if he was expecting company, a big smile came across his face as he said that he was hoping to see a young lady in a while.

I looked him in the eye and said that he should pour the wine, then i headed upstairs. I went straight to the bedroom and opened the top drawer, and picked out a black corset. Next i selected a pair of black stockings and a pair of lacey black knickers.

I opened the wardrobe, trying to find something that would make me feel sexy. I found a blue silky dress, long sleeves and a crew neckline, it had a slit up the sides. I laid the clothes on the bed and found the high heels that Jim had bought for me.

I quickly stripped, excited at the thought that i was about to dress up as a woman, to please a man. The corset was tight against my body, it felt so sexy. I slipped the stockings up each leg, almost gasping with pleasure at the feel of them, excited as i attached each clasp to them. I stepped into the knickers and pulled them up, then stood in front of the mirror, breathing heavily as i stroked the sexy underwear.

I sat down with the makeup, applying foundation and fixing powder. I decided on dark blue eye shadow. The black eye liner making my eyes really stand out. Thick mascara was next, then i highlighted my eye brows. A little blusher made my cheeks look amazing. I finished with bright red lipstick, always loved putting on lipstick.

I put a little gel in my hair, my hair is short and dark, i gave myself a shaggy style. To complete the look i clipped on a pair of silver, dangly earings. I slipped in to the dress, the neckline tight around my neck. The slits up each side showing off my stockings nicely. Slipping on the high heels, i couldn't resist a little giggle. The woman looking back at me in the mirror made me feel incredibly feminine.

I took the lipstick with me as i left the room and went downstairs. At the bottom of the stairs, i took a deep breath, then headed for the living room. I stopped in the doorway, putting a hand on my hip, i asked Jim if i could join him for a drink.

Jim's eyes widened and a huge smile lit up his face. Jim was in his armchair, two glasses of wine were on the table. He waved me over and pointed at the sofa opposite him. I walked slowly, teasingly, towards the sofa.

I could see that Jim was pleased, he told me that i looked wonderful and kept saying wow to himself. I sat down, trying to be as female as possible. The slit, in the dress, showing Jim that i was wearing stockings.

I smiled and picked up my glass, saying cheers to Jim as we clinked glasses. As i took a sip of the wine, Jim said that i looked beautiful. This sent excitement through my body and i thanked him. I crossed my legs, smiling at the lipstick marks on my glass. Jim asked me if i would do something for him, and i told him yes. Jim handed me a bottle of perfume, saying that it was his wife's favourite fragrance. I gave my neck a quick spray, then squeezed a few sprays into the air.

There was silence for a while, as Jim kept looking me up and down. Halfway through my wine i got up and walked around the room, letting Jim take it all in. I was turned on by the thought that Jim wanted me, slowly i walked over to him. As i got to his chair he stood up.

He was taller than me, and i had to look up at him. Jim slid his arm around me, pulling me into him, i gave a little squeal. Jim said that i smelt lovely, then straight away, Jim leaned in and kissed me. I responded, my hand pulling his head in, while the other reached round his back.

Jim held me tight, as our tongues explored each others mouths. It wasn't rushed, slow and meaningful. Jim's hands gently stroked my back, rubbing my arse. I stopped kissing, looking up at Jim, my lipstick smeared around his mouth, i told him that i wanted him to make me a woman.

I put my hand on Jim's bulge, rubbing his hard cock through his trousers. As i looked him in the eye, i whispered to Jim that i wanted him. Jim let out a groan, then asked if i had a feminine name. I stood on tip toe and kissed him gently on the lips, Delia, i said in a hushed voice, call me Delia.

Before Jim could reply, i dropped to my knees, excitedly undoing Jim's trousers,

pulling them down, along with his underwear. Jim's very hard cock, stood to attention, begging to be sucked. I frowned and looked up, mock confusion on my face. Jim smiled and said my name, Delia, i took a deep breath, then heard Jim telling me to put him in my mouth.

I wrapped my hand around his shaft, and did as i was told. Gently i sucked on his shiny helmet, as Jim called me a good girl. Jim took his jumper off, then his shirt, as i continued to work on his manhood. Jim was naked, he gently stroked my hair, telling me what a good girl i was.

After a few minutes i stopped, getting to my feet as i looked Jim in the eye. I took him by the hand and led him to the sofa. Jim sat down and i stood between his legs. With one foot on the floor and one foot on the sofa, i showed Jim my stockings and knickers, Jim was breathing heavy as he started to stroke my leg.

I asked Jim if he wanted me, his eyes opening wide as he nodded. I bent forward and kissed him, i whisper to him that he will have to get me ready to take him. I get on my hands and knees on the sofa, facing away from Jim. A few seconds later i feel Jim gently stroke my bottom, then i feel my dress being pushed up and over my back.

I hear Jim moving behind me, then my knickers are pushed down, i lower my head to the cushion, Jim slowly slides a finger down between my cheeks and i sigh with pleasure. He opens the lube and smears the slippery liquid over my tight hole.

My stomach turns excitedly as Jim pushes his finger against my hole. I let out little moans of pleasure as the pressure increases, then i let out a whimper as i feel Jim's finger enter me. He shushes me as he tells me it's okay, easing his finger further into my tightness.

Jim isn't rushed, taking his time to slip his finger in to me as far as he can. I let out hushed moans as Jim fingers me. After a while he pushes a second finger in, i groan as he talks quietly to me, again calling me a good girl, calling me Delia.

After a few minutes Jim stops, telling me to take my knickers off. He is stroking his cock as he tells me to go to the end of the sofa, im told to bend over the armrest. My dress is lifted and pushed up my back, i look over my shoulder and pout, asking Jim to be gentle with me.

I can hear him breathing heavily, then i feel his warm cock as Jim slowly slides himself up and down between my arse cheeks. I feel Jim's helmet as he guides it to my hole, biting my lip as i feel him begin to push. A minute or so passes, then i feel a pop as i finally relax enough to allow Jim's helmet to enter me.

I let out a loud gasp and push myself up, Jim shushes me again, calling me a good girl over and over, as he holds my hips. He pushes again and i stretch over Jim's bulging helmet. I pant and ask him to stop for a minute, and he does. After a pause, i tell Jim to carry on.

I lower my face to the sofa, soft groans as i continue to stretch and accept Jim's long hard cock. When he is about half his length in me, he stops, and starts to withdraw. I pant and gasp as the pleasure/pain floods my body, then i let out a long whimper as Jim again, pushes back into me.

Jim grips my hips, telling me how tight i feel around him. He works a slow rhythm for a while, telling me that im a good girl. The sound of him calling me Delia and telling me how sexy i was, really turning me on. I wanted his full length inside me, i push back, encouraging Jim to fuck me.

He starts to pump my tight hole harder, his long hard cock filling me up. I look over my shoulder and through gritted teeth, i tell Jim to cum inside me. I beg him to make me a woman, to fill me with his cum. Jim's strong hands grip my hips. He growls at me, calling me a dirty girl, as he gives me a few hard thrusts, then he almost shouts as he starts to shoot his warm cum inside me.

I groan loudly, as Jim gives four or five deep thrusts. He holds himself inside me for a while, as he gasps in air. I say thank you to Jim, telling him that he was amazing. He slowly pulls out of me, my hole aching and throbbing. Jim sits in his chair as i stay where i am for a while. I ask if he is okay and he smiles and nods.

I get up and pull my knickers back on, straightening the dress. I walk to the mirror and reapply my lipstick. I sit opposite Jim and pour some more wine. Jim looks at me and says thank you. I smile at him and tell him that it was my pleasure, telling him how wonderful he felt inside me.

As Jim puts his clothes back on i watch and sip my wine. Once dressed, he walks up to me, leans down and kisses me. We kiss for a few seconds, Jim pulls back and tells me that it's been a long time since he has been with a woman. I blush and say thank you, i tell him that i would love to visit him again very soon.

We sit and chat for a while. We talk about getting some shoes and younger looking dresses and things. I tell Jim that id be happy to wear whatever he wanted me to. After another glass of wine, i go and change. I promise to visit him again very soon, then, with a smile on my face, i make my way home.

Delia365
Delia365
165 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
cdCindy1cdCindy1over 1 year ago

Love this story. I too would love to be a "woman" for an older man. I want him to lean down and kiss me, feed me his big cock and then fuck me -- make me feel his big cock inside me and breed me like a stud breeds a sissy faggot like me.

I can't wait to read more of your stories. This one is great.

88girfriend88girfriendover 1 year ago

I always say the devil is in the details and your details are spot on. I love the fact that you're talking about how the lipstick smeared and that jim has Delia wear his wife's favorite perfume. That just sent Shivers up my spine. please keep writing more.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Comforting Pete Consoling friend reluctantly agrees to help in other ways.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
Fishnets / French Maid He wears his ex-girlfriend's lingerie - accidentally fucked.in Transgender & Crossdressers
Trophy Wife Dumped by his Fiancée, Eric finds comfort w his Best Friend.in Transgender & Crossdressers
More Stories