Neighbours suprise

Jim lived down the street from me and was in his 70s. He had been on his own for a while, his wife passing away a few years ago. He was a tallish man, i imagine that he was quite handsome in his day. He was carrying a few extra pounds now but you could tell that he was once quite muscular.

I had spoken with Jim many times, helped him out when he needed an extra pair of hands and even had coffee with him from time to time. I got the impression that he was a lonely man and enjoyed chatting with people.

One day Jim asked me if i could help him move some things for him, put a few boxes in the loft, that sort of thing. I had nothing planned so I said yes. We had a coffee and a chat, before going upstairs and opening the loft.

In the spare bedroom there were some empty boxes and bags, Jim asked if I could empty the draws and wardrobes, put everything in the boxes and put them in the loft. I said yes and Jim said that he would make us something to eat, leaving me to get on with the job in hand.

The first few cupboards and drawers had books and paperwork, photo albums, that sort of thing and i started to fill up the boxes. Then I opened the drawers next to the wardrobes.

The top drawer was full of tights and stockings and knickers. The next one had bra's and corsetry, i ran my hands over the soft, silky, Lacey garment's. I picked up a pair of tan tights, slipping my hand inside them, feeling them stretch and cling to my hand.

I sat on the bed, watching my fingers stretch the tights. I stroked my face, excitement building up inside me. I don't know how long i was sitting there but i was suddenly aware that Jim was watching me.

I pulled the tights off my hand, apologising to Jim. I felt myself blushing, embarrassed, i put them back in the drawer and pushed it shut. Jim smiled, saying that it was okay and not to be embarrassed.

Jim sat down next to me and opened the drawer, picking up the tights. He turned to me and asked if I liked the feel of them, i apologised again but Jim just smiled and repeated the question, i nodded.

Jim then asked me if i had ever worn a pair of tights, i shook my head and said no. Jim stared me in the face and asked if I was telling the truth. As i looked back at him i found myself saying no, then telling him that I had worn my sister's and mother's clothes.

Jim smiled and handed me the tights, he stood up and opened the wardrobe, hanging up were dresses and skirts. He asked if I saw anything that i liked, i smiled and said yes. Jim then asked me if i wanted to try anything on, i looked at him, not quite sure what to say. Jim then asked if i would wear a dress and underwear for him.

As Jim left the room, he said that he would be downstairs in the living room, that it was okay whatever i decided. The door shut and I stared at the clothes, then started looking to look at the dresses.

My eyes were drawn to a velvet blue dress, i took it off the hanger and laid it on the bed. The long sleeves were sheer and the velvety feel of the material was amazing.

I stripped almost immediately, almost breathless as i slipped the tights up my legs. I picked out a pair of blue knickers, they fit perfectly. A blue bra was next, not a bad fit. Putting on a bra always felt fantastic, very feminine.

I picked up the dress and pulled it on. It was a little big but felt wonderful. The sheer sleeves made me smile, i felt so excited, almost breathless. I went through the shoes and found a pair of black flats, they pinched a bit but i liked them.

I took a deep breath and opened the door. i went downstairs and into the living room. Jim was sitting in an armchair. I stood in front of him and asked him what he thought, a huge smile told me all i needed to know.

He asked me how i felt and I told him of the excitement i felt inside. He told me to walk around the room, i loved the feel of the dress on the tights. He asked if I would show him what knickers i was wearing.

I lifted up the dress, showing Jim the blue knickers, i turned round to show him my bottom, he liked that. He sat up and leaned forward, i told him that he could touch the knickers if he wanted to.

Jim stroked them softly, then he stroked my tights. I gasped, enjoying the feeling. I opened my legs slightly, allowing Jim to move his hand up and down my inner thighs. I heard the chair creek as Jim stood up, i tensed for a moment, wondering if i had gone to far.

Jim tells me to stand up straight and turn round to face him. I nervously turn round but all worry disappears when I see a smiling Jim, or more importantly, the bulge in his trousers. He tells me that i look lovely dressed as a girl. He asks me if i enjoy being feminine and i whisper, yes. Jim looks down at his bulge, then looks me in the eye, raising his eye brows.

I smile, getting the hint. I get on my knees, unbuckle his trousers, tugging them down. Without pausing i pull his boxers down aswell. Jim's cock was rock hard, about 8 inches long and his helmet was shiny and bulging.

I look up at Jim and let him know that I am impressed. Still looking up, i lean forward and kiss the shaft, this produces a gasp from Jim, he throbs hard. I kiss it again then lick him, he oozes as he watches me.

I take him in my hand, teasing his helmet with my tongue, then I take him in my mouth. As my lips close round him he groans and calls me a good girl. I gently suck, slow at first, trying to take as much of him as possible into my mouth.

He puts a hand on my head, telling me that he is about to cum. I suck and tease a little faster, he tells me again that he is going to cum but I carry on. Jim stiffens and let's out a moan as he starts to cum, i swallow it all and keep sucking until he can't take it anymore.

Jim sits back in his armchair, panting and saying thank you. I'm still on my knees as I ask if he is okay. He says yes many times, apologising for not lasting very long. I smile at Jim and tell him that it's okay, that i enjoyed it.

I sit on the sofa opposite him, Jim thanks me again and i smile. I ask him about the clothes and he explains about not being able to get rid of them after his wife passed. I ask if he still wants me to put the clothes in the loft. Jim stares at me, he asks if i would be interested in them and i explain that I have nowhere to put them. Then he says that if i wanted, the clothes can stay where they are, and i could visit him and dress up whenever I wanted.

I get up and walk over to Jim and hug him, telling him that I would love that. I tell him that in return id be happy to repeat today's little fun. Jim grins and says thank you.

A few days later i decided to go and see Jim again. I knock on the door, it's not long before he opens it, smiling, he invites me in. We go through to the living room and sit down, Jim smiles and says that he wondered if i would visit him again, pleased that i had.

I ask him if i can go upstairs and dress up, he tells me that he would love it if i did. Jim says he will put the kettle on and wait in the living room if i wanted to join him.

I open the draw with the corsets in, spoilt for choice, i pick out a red one. The suspender straps hang from it and i lay it on the bed. I look through the top draw and find a pair of tan stockings, then pick out a pair of red knickers.

The wardrobe is full of dresses and skirts, mainly for the older woman, but I find a few dresses that i like. I pick out a black dress with red flowers on it, then i strip.

The corset fits me well, i love the way it stretches and hugs me. I slip on the stockings, attach the straps and slide the knickers up. I look in the mirror, stroking the corset, the way that the straps pull on the stockings makes me feel sexy.

I pull the dress on and straighten it out, it goes down to my knees. It's not too tight but you can make out the stocking straps. The sleeves come about half way down my arms. I struggle to find a pair of heels that fit properly so I settle for the flats that i wore last time.

I take a deep breath then go downstairs. Jim is in his armchair and there is a cup of tea on the table. I walk in and stand in front of him again. He smiles and tells me that the dress looks good on me. I sit opposite him and we start to chat.

I deliberately sit on the edge, so that Jim can get a glimpse of the stocking tops. It's not long before he asks me to walk around the room, asking if he can see my underwear. I willingly do this, teasing Jim as he watches me.

I stand in front of him and invite him to touch my legs. He fingers the stocking tops, then slides his hand up to my knickers. I lift my dress and turn round, Jim's hands gently touch my arse. After a few minutes i turn round again, as Jim stands up, i drop to my knees.

Jim's big cock is rock hard, as I release it from his underwear, it springs up. I take it in my hand and look up at Jim, then lick his shaft. Jim let's out a groan as I lick him again and again. His helmet is oozing and I gently lick the pre cum up, then take him in my mouth.

Jim's hands touch my head as i softly suck him, slow gentle movements. I can hear Jim's little moans as I suck his hard cock. I stop and tell Jim to sit down on the sofa, then i kneel on the sofa beside him.

I masturbate him, asking if he is enjoying himself. He nods and smiles. I go down and start to suck him again, lifting my dress up as i do so. Jim reaches out and starts to stroke my knickers and stockings.

I bob up and down on Jim's big cock, licking and teasing his helmet, he slips a hand inside my knickers and squeezes my arse cheek. I feel him stiffen and his hand touches the back of my head.

I go a little faster and then Jim groans loudly as he shoots warm cum down my throat. I keep going until he can't take it anymore. I sit up on my knees and smile at him as he catches his breath. He says thank you to me and i tell him it was my pleasure.

I say to him that he lasted a lot longer this time and he laughs. I go to the kitchen and make some more tea. Jim is dressed and back in his chair as I put the tea on the table.

As we chat Jim asks if I had ever been with a guy before and i tell him about a couple of experiences that I had had. He asks if i would ever let him have sex with me. I smile and grip his hand, i tell him that i would be happy for that to happen.

I tell him that we could have many experiences together if he would like. I go and change, telling him that i will visit again soon.