Neighbours suprise Ch. 06

Story Info
The urge to dress up and pleasure Jim took over my thoughts.
3.2k words
4.67
5.1k
11
Story does not have any tags

Part 6 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

Jim was an elderly gentleman that owned a house close to where i lived. His wife had passed away some time ago and he lived alone, i had checked up on him from time to time and helped him out when he needed an extra pair of hands. On one such occasion Jim had asked me to help him fill some boxes and put them in the loft. I had opened some drawers filled with lots of tights and ladies underwear, i couldn't resist touching the wonderful array of female garments. Jim discovered me holding some items and this led to me confessing to him that i enjoyed wearing women's clothing. I had dressed up for him that evening and ended up giving Jim a blow job. Since then i had visited Jim on many occasions and enjoyed dressing up and having sex with him.

.......

One particular evening the urge to visit Jim and dress up as a woman had taken over my every thought. I decided to go round to his place and see if he would be happy with a visit. I knocked on Jim's door and didn't wait long before he answered. Jim smiled and invited me in straight away, i immediately asked him if he was happy to have some company, and before he answered, i asked if i could go and get dressed, he nodded as he said yes, then waved his hand toward the stairs.

I was almost out of breath with excitement as i headed up the stairs and went straight to the room and started to strip. I had taken a black corset with me, it was my mother's and i had worn it a few times before, it felt incredible and never failed to make me feel sexy. After pulling on the corset i went to the underwear draw and picked out some black stockings and a pair of black lace knickers. I attached each stocking to the suspenders and pulled up the knickers, i gasped with delight as i ran my hands over the sexy garments.

I sat down and applied some makeup, dark grey eye shadow and black eye liner then thick black mascara. I used some gel on my hair and gave myself a kind of sexy scruffy style then, as always, used bright red lipstick to complete the look. I slipped my feet into a pair of shiny black high heels before putting on the little silky pink dressing gown. I had a final look at myself in the mirror and admired the sexy woman that looked back at me. I sprayed Jim's favourite perfume over my body and neck then took a deep breath and headed downstairs to the living room.

I walked to the middle of the room and put my hands on my hips and smiled at Jim. He sat up straight, a look of suprise on his face, and started to tell me how sexy i looked. I turned round a couple of times and opened my dressing gown to give Jim a proper look at what i was wearing, i wanted to get Jim fully aroused. As i paraded in front of Jim i let the dressing gown slip off of my shoulders, then stood right in front of him. I looked down at Jim as he sat in his chair, and told him that i was going to fuck him senseless until he couldn't take it anymore.

Jim rose from his chair and stood in front of me, he towered over me and i suddenly felt very small and feeble. He put his hand on my shoulder, then bent forward until our mouths met. As our lips touched and our mouths opened, electricity shot around my body, the kissing instantly became passionate. I broke the kiss after a minute or so and put a hand on Jim's chest, i gently pushed him backwards towards the wall, i stared him in the face as i told him that i was going to take charge.

As Jim's back met the wall, i undone his belt, and growled at him that i was going to suck him dry. After i unbuttoned his trousers, i dropped to my knees and pulled them down along with his underwear. Jim's big cock sprung to attention in front of my face, rock hard and throbbing. His cock was very impressive and i admired it for a few seconds before taking it in my hand. Jim gasped as i gently stroked his length, i told him that i wanted him to cum in my throat then started to lick the tip of his oozing helmet. I kissed and licked his shaft, Jim groaned and encouraged me, i made my way to his balls and began to nibble each one in turn, still stroking his manhood.

I couldn't wait any longer and i started to suck Jim's helmet, taking more and more of him into my mouth as i began to bob my head. Jim groaned loudly and placed a hand on my head, he called me a good girl as he watched me suck his rock hard manhood. I was very aroused and eager to make Jim cum, id stop sucking every so often and masturbate him furiously as i encouraged him to explode. Eventually Jim groaned that he was going to cum, i took him back in my mouth and i greedily sucked as i waited for my reward. Jim's whole body seemed to tense as he loudly sucked in air through his clenched teeth, then he began to shoot his thick, warm cum down my throat. I almost choked as the first load hit the back of my throat but i kept going.

Jim came lots and shot load after load into my mouth, i continued to suck until Jim couldn't take it anymore. As he removed his cock from my mouth i looked up at him, i stuck my tongue out and showed him what was left of his thick man juice, then closed my mouth and swallowed. Jim breathed heavily as he leaned against the wall, he smiled and said thank you to me, he told me how sexy i was as i got to my feet. I stood in front of him then leant forward and kissed Jim's lips. I told him that i was going to sort out my makeup and asked him to pour me a drink, as i picked up my dressing gown, i turned to him and said that i hadn't finished with him yet and there was more to come.

I sorted out my makeup and reapplied my lipstick, touched up my hair and put the dressing gown back on. Jim had poured a couple of glasses of wine as i re-entered the living room and was sitting on the sofa. I sat down beside him and asked if he was okay. Jim said that he was and thanked me again, he said that he hadn't expected me to come round but was very happy that i had. I sat close to Jim as we chatted and drank, my foot rubbed up and down his leg and i really flirted with him, touching him as we spoke. The urge to please Jim was getting stronger and i was still very aroused.

About an hour had passed as we chatted and drank. I put my glass down and knelt on the sofa beside Jim. I took his drink from him and put it on the coffee table, then told Jim to kiss me. Again our mouths met and we kissed, Jim went to put his arms around me but i pulled away. Jim stared at me and frowned, i looked him in the eye and growled at him to take his clothes off. Jim paused a second and i repeated myself, telling him to get up and strip. Jim got to his feet as i knelt on the sofa. He faced me and did as i had asked. He removed his cardigan, then unbuttoned his shirt, i knelt and watched as Jim took off his shirt and dropped it to the floor with his cardigan.

I tingled all over as i watched Jim unbuckle his belt and unfasten his trousers, i was almost panting as he pushed them down along with his underwear. Jim was obviously aroused but not fully erect as he stood naked in front of me. I looked up at Jim and told him that i wanted his cock rock hard, then i wrapped my fingers around his warm manhood. Jim stepped closer and i immediately leant forward and took him in my mouth again. As i gently sucked on Jim's tight helmet i felt him swell and throb. It didn't take long to get him fully erect, at which point i got up from the sofa.

As i stood in front of Jim i felt very small. I had to admit, for a man of his age, he had a great body. Thoughts of submitting to Jim crossed my mind but i quickly shrugged them away, i was the one taking charge tonight. I pointed to the floor and told Jim to get down and lay on his back. Jim did as he was told, and i stood over him, i looked down at him as i took off and dropped my dressing gown to the floor. I told Jim that i was going to fuck his brains out as i stepped out of my knickers and stood astride of him. I smeared lots of lube over my pussy then knelt down, my stocking clad legs either side of Jim's hips. I put my hands on Jim's chest and rocked gently back and forth as i described what i wanted to do to him, i could feel Jim's cock as it pressed against my arse cheeks.

Jim breathed heavily beneath me, i reached behind me and guided his helmet to my willing hole. Our eyes were locked on each other as the tip of Jim's cock pushed against my pussy. I pushed back and felt myself stretch as Jim began to penetrate me. I began to pant then gasped loudly as my tight pussy finally gave up the fight and allowed Jim to enter. Jim groaned and his whole body tensed as i continued to allow his rock hard cock to penetrate me deeper. I put my hands back on Jim's chest, his manhood fully and completely inside me, then told him again that i was going to fuck him senseless.

I took a couple of deep breaths, i could feel Jim throbbing inside me, then i began to rock back and forth slowly, my lower body felt incredible and with every movement of my hips, i groaned with pleasure. Jim stroked my stockings and i picked up the pace, he called me a naughty girl and encouraged me, which just excited me more. After a few minutes i leant back, i put my hands behind me and raised myself up until my heels were planted firmly on the carpet. I moved as fast as i could, riding Jim like there was no tomorrow, forcing him to gasp and moan uncontrollably. I was taken over with the urge to please Jim, lost in the moment and full of lust.

Several minutes later i suddenly stopped, i lifted myself up until Jim's cock slipped out of my pussy. Without pause i turned around and began to suck Jim's sticky wet cock, i could taste myself on him. I sucked Jim for a while before i got to my feet, i told Jim to get up and sit down in the middle of the sofa. Jim did as he was told, i turned my back to him and then lowered myself down onto his lap. Jim manoeuvred his spit covered erection toward my gaping pussy as i sat down, he easily entered me and i took his full length. Jim held my hips and began to pump me hard and fast, i pushed my back against Jim's chest and he kissed and bit my neck and shoulders.

I raised my feet up onto the sofa and ground down into Jim's lap, his rock hard cock throbbed inside me. I rocked back and forth until the muscles in my lower body suddenly spasmed and i spurted, shooting warm juices into the air, this made me shudder and i almost collapsed. My whole body trembled and i had to stop moving. Jim stopped pumping my pussy as i regained my senses, i panted heavily as i sat on Jim's lap. He spoke in a whisper and again called me a good girl and told me how sexy i was. I was so aroused and excited, i wanted Jim to fuck me hard, i got up off his lap and took him by the hand and told him to stand up. I led him to the arm of the sofa, and then i bent over, almost angrily, i told Jim to fuck me hard.

My throbbing pussy ached as i waited for Jim's cock to enter me again. Jim didn't need to be told twice, he pushed his thick cock straight into me making me squeal. He grabbed my hips and immediately started to pound me hard and fast. My eyes were shut tight and i buried my face in to the cushions as i groaned loudly. Jim's full length slid in and out of my tight hole as he kept up the pounding, the sound of his body as it slapped against mine was intoxicating. Jim put his hands on my back and began to push me down further into the sofa cushion. He called me a little whore and a dirty girl, as well as other names, i growled back at him to pump me harder.

Jim almost roared as he began to cum, he grabbed me roughly around the hips and then exploded. He shot load after load of his thick cum into my pussy, he thrusted hard with each ejaculation. I groaned with satisfaction as i encouraged him to fill me up. Jim pushed deep into me and held himself inside me for a minute or so as he caught his breath. I told Jim how good he felt inside me, and then told him how much i enjoyed the pounding he had just given me. Jim withdrew from my pussy slowly and stood over me, he said that he loved how tight i felt on his cock and that he had cum hard.

Jim withdrew from my hole and collapsed into the sofa. I got to my feet and smiled at him and told him that i was going to the bathroom to sort myself out and to get him a towel. I picked up my knickers and gown and headed upstairs. After cleaning myself up, i put on my gown and knickers then reapplied my makeup and headed back to the living room. Jim had put on his underwear and had regained his breath, i handed him the towel and sat beside him again. Jim put a hand on my knee and told me how sexy i was, i thanked him as i sank back into the sofa, then i said that i hadn't finished with him yet. Jim laughed and shook his head, he said that he didn't have anything left in him, i said nothing as i smiled back at him.

We continued to drink and chat for some time, Jim let me know how much he enjoyed our time together and how our visits had brightened up his life. I admitted to Jim that i too loved visiting him and dressing up for him. I put my hand on Jim's arm and slid closer to him, pushing his arm over my shoulder. I stroked his chest and moved upwards, then put my hand on Jim's face. I moved my mouth to his and gently kissed him, little pecks became firmer kisses, then passionate and loving. I became very aroused very quickly and slipped off the sofa, then i got between Jim's legs. With both hands on his underwear i pulled them off, Jim gave a half hearted protest. He wasn't fully erect and he told me that he wasn't sure if he could perform again.

I ignored Jim as he spoke and went down on his manhood. I softly sucked and licked Jim's cock, i could taste our sex from earlier on, i was determined to get him hard. After about ten minutes my hard work started to pay off, Jim's cock began to swell and grow. I kept going until Jim's long thick cock was fully erect. I stroked his length as i looked Jim in the face, then growled at him to fuck me again. As i got on my back on the floor, i removed my knickers and opened my legs, then invited Jim to get between them. Jim knelt down and pushed my legs further apart as he got on top of me. He looked down at me as he pushed the tip of his helmet against my hole, then grunted as he pushed in and stretched me open.

I groaned loudly as Jim pushed deeper inside me, my legs lifted and squeezed against his hips. Jim held himself up with his arms, my hands grabbed them, we stared at each other for a second or two. Jim began to slowly fuck me as we looked at each other. As Jim increased his rhythm i wrapped my legs around his waist and moved my hands up to his shoulders. Jim lowered himself on top of me and we started to kiss, i then wrapped my arms around him and held him tightly. We stopped kissing as Jim began to fuck me harder and faster. I pulled him against me and whispered in his ear to fuck me harder and harder. Jim's face was buried in my shoulder and i squeezed my stocking clad legs tighter around his waist as satisfied groans left my mouth.

Jim's body tensed and i gripped him harder, i gasped at him to fill me up. Jim thrust hard and buried his full length into me, he almost growled as he exploded, shooting cum deep inside my pussy. He gave four or five hard thrusts, each thrust pumped more of his man juice into me. Jim finally collapsed on to me, he gasped for air as he lay still, my arms and legs still wrapped around him. I let Jim know how good he felt inside me, i told him that i felt incredible, that i loved having sex with him. Jim found the strength to lift himself up, he breathed heavily as he stared at me, and said that he couldn't believe that he could cum so much. He called me sexy and said that i made him feel ten years younger, then leant down and kissed me.

As Jim got to his feet he thanked me over and over again. I let him know that i he didn't need to thank me, that i enjoyed our time together just as much. I gathered my things together and went upstairs to clean myself up and get changed. After changing i went back to the living room, Jim was half dressed and sat on the sofa. I leant over the back of the sofa and wrapped my arms around Jim and whispered into his ear that i would visit him again real soon.

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
3 Comments
4Leather4Leather7 months ago

Another sexy chapter in the sissy pleasure of care giving a friend. Door is still open for the next chapter. XXXX

AnonymousAnonymous8 months ago

I love it, what a sexy story, I hope you write another chapter soon xxx sissy Lucy

JgsexyJgsexy8 months ago

Lovely tale of a lovely evening!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Comforting Pete Consoling friend reluctantly agrees to help in other ways.in Transgender & Crossdressers
Adele finally becomes a Sissy Caught dressed as Adele.in Transgender & Crossdressers
Hired for a Poker Party Waitress for a poker party and more!in Transgender & Crossdressers
Getting Caught My friend discovers my Lingerie secret.in Transgender & Crossdressers
Fishnets / French Maid He wears his ex-girlfriend's lingerie - accidentally fucked.in Transgender & Crossdressers
More Stories