When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I indulged my habit.
When we first moved to my home town when I was very small there was a family next door who had kids the same age as me and my siblings. We all became friends and ended up with a gate between our fences so we could go back and forth. Eventually though they moved houses and a new couple moved in, Eleanor and Geoff. He was a little older and clearly had a lot of money. He had married a woman much younger than himself and certainly more attractive than he should have been able to. She was incredibly sexy too; in her late thirties to his mid-fifties, sandy blonde hair, green eyes, and a figure she maintained with regular trips to the gym. She was, after all a kept woman.
Being a friendly family, we introduced ourselves and always offered a helping hand for things so the gate remained. They would holiday often so we could look after their house in their absence plus they had a huge TV and they didn't mind me going around to watch it. Of course when they weren't around I'd make the most of it and borrowed some of her things. I always admired her fashion sense, beautiful dresses and outfits that I loved to explore whenever I had enough time alone. She clearly took plenty of advantage of her husband's bank balance with designer clothes and expensive lingerie.
Being that I was 18, Geoff and Eleanor didn't seem to mind having me around, I would often spend most weekends in and out of their house and I usually knew their plans well in advance so I could make the most of their empty house. On this particular Friday I arrived and Geoff was not yet home which I expected. I'd been told that Eleanor would also be away until Sunday, so I was looking forward to a few hours alone before Geoff came back from work so I was a little disappointed to see Ellie's car in the drive when I arrived.
I let myself in and found her enjoying a cup of tea in the kitchen. I greeted her and we chatted. We always got on well, sharing a taste in films and such. As we talked she said there was something she wanted to bring up. I felt my stomach tie in knots instantly. She explained that she wasn't angry but that some of her things had been moved. That she knew I'd been going through her things and she wanted to know why. I had always been honest with her and, for some reason, I felt I could open up to her. I told her that I would wear her clothes and that I enjoyed wearing women's clothing. We talked about it and she was so understanding. She swore she wouldn't tell Geoff or anyone else but also asked that I don't do it any more. I of course, agreed. She seemed pleased and while I was a little disappointed it felt good to be honest.
The following day Geoff went to watch a football match and Ellie went out. Their empty house seemed to call out to me but I managed to resist! Ellie returned home in the afternoon and came to find me. She explained that she had checked and believed I had not been into her things and that she was grateful. To show her gratitude she produced a travel bag. She explained that she had been shopping and bought a few things but there were a few conditions attached. I was still to keep it a secret, she didn't think appropriate that I dress up while she was around, and that I continue to respect her things. She explained the bag would be in the wardrobe of the guest bedroom so that no one in my house could find it and that from time to time she would buy me things. She had noticed how disappointed I was the previous day and wanted to reward me for my honesty.
She placed the bag on the table between us and fetched some bags from her car. I watched as she produced various items from them. She seemed to enjoy placing the items in the hold all, telling me what she'd bought as she went.
"This cute dress!" she said, "oh and this baby doll nightie is quite adorable! And these stockings will go so well with this set." I was speechless as I saw her finally produce two pairs of high heels for me. Between lingerie, dress, skirts, tops, and shoes I had more than enough to keep me happy for a long time.
"Wow, thank you!" was about all I could muster from my excitement.
Over the following weeks and months I would relish going through my new clothes and wearing my own things. Sometimes new items would arrive and soon half of the wardrobe was taken over. Geoff never ventured into the guest room, let alone going through the closets. The things bought for me were definitely Ellie's style too. We'd talk about it occasionally when we were alone. I would thank her for things or she would ask if I liked certain garments. Conversationally we became very open about it and she began asking what I liked and a few times we would look at clothes together online. On one occasion she caught me eyeing up the dress she was wearing and the following weekend I found my own identical one hanging in the wardrobe.
One Saturday morning I knew Geoff had planned a day out in London for himself and his trophy wife. I had slept in that day and when I woke I walked to the window and looked into the driveway to find my Geoff's car gone. I decided I would take full advantage of the empty house next door. I went unseen to the back garden and through the gate. Among my things in the spare room I found a beautiful cream lace nightie with matching panties and put them on. It felt wonderful!
I tied back my long dark hair and dug out a few pieces of make up I had. Before applying I decided to get a drink so I slipped a soft satin dressing gown on and headed to the kitchen. As I padded gently around, preparing my beverage I heard Ellie's voice in the lounge as she spoke on the phone. I must have moved too silently for her to hear me come in. Despite her knowing about my dressing I still panicked slightly, especially as I heard her approach the kitchen.
"Ellie, sorry! I thought you were out!" I called out as crept past her. She looked a little surprised but not shocked as I disappeared up the stairs and back to my room. I shut the door behind me and cleared my make up away when there was a knock at the door.
"Sorry sweetie," Ellie called through the door. "Geoff had to work today."
"It's okay," I replied. "I'll just change." She was silent for a moment.
"I can go out if you like?"
"No, no, it's fine." I could hear her still outside my door.
"The dressing gown suits you," she said.
"Ummm... Thank you. I like it." I was a little confused at this.
"May I come in?" she asked. I went to the door and opened it a crack. Poking my head around so only my face was visible in the gap.
"I haven't changed yet." I explained.
"Sweetheart, I've spent hundreds buying you things and I've often wondered how well they would suit you." After a brief pause I opened the door. The only people who had seen me even remotely dressed before had been people I was seducing so this was quite alien to me. Ellie looked at me. The soft, cream coloured, satin robe was wrapped around me, the lace trim reaching nearly to my knees. I looked down and saw it had opened slightly to reveal the fine lace of my nightie underneath. I quickly pulled my robe tighter around myself to which Ellie smiled. "I thought you may like that. I bought one for myself too. You have such a lovely figure." She reached out to my knee and tutted. "Shaving the knee is so tricky. Wait here!"
She disappeared off down the hall as I stood slightly dumbfounded. She quickly returned with some hair removal cream and handed it to me explaining what it was. She said that she insisted I take a shower and use it and that she would make herself scarce. I tried to protest as it was her house and I didn't want to turf her out so that I could have fun but she would not take no for answer. With that I did as I was asked, taking myself off to shower and removing every tiny little bit of body hair. As I returned to the guest room room I was surprised to see Ellie sat waiting for me.
"I'm sorry I couldn't resist. I was going to go but then I got thinking about some of the things I'd bought you and you looked so good I just wanted to see what you looked like in this." She pointed to the wardrobe upon which she'd hung out a black satin wiggle dress. "When I saw it I had a great idea of what your hair should be like too. Can I do it for you please!?" She seemed so excited I couldn't help but be more than a little excited too. I agreed, of course, and she almost jumped into the air with joy.
"Okay, I'm going to get a few things so if you want to put some underwear on and put your robe on I'll be right back."
Once again she disappeared down the corridor. I'd worn the dress she had picked a few times before and I knew how figure hugging it was. I went to my lingerie and found a black and red lace bra, matching thong, and matching suspender waspie that sinched my waist just so. I also found some beautiful retro seamed stockings. As I wrapped myself in that gloriously beautiful lingerie I felt amazing.
Those fitted seamed stockings felt delicious as a ran them up my soft smooth legs. As I attached the final suspender clasp to the smooth stocking top I couldn't help but admire myself in the mirror. My gentle curves accentuated by the soft lace. To see myself like that, the only give away being the slightest bulge of my cock tucked back inside my panties. Lost in the moment I suddenly heard Ellie outside my door. I quickly wrapped the robe around myself again as she came in.
She had with her a few things but I noticed first that she herself was in a silk robe. She explained that she didn't want to get make up on her clothes before sitting me down. My hair is long and runs most of the way down my back. Normally it's straight and she began to gently brush it for me before pinning it up in large rollers. We talked the whole time as she styled my hair before she moved on to my make up. It was incredibly thrilling. Her face got close to mine. Her robe fell open slightly and I could glimpse her firm breasts held in the soft lace cups of her bra. I think she noticed I was getting a little flushed as she asked if I was okay. I said I was fine but she smiled at me before leaning into me.
"It always turns me on a little too. When I dress up in something sexy. " She continued and before long she was removing the curlers from my hair and styling it for me. Once she had finished I admired myself in the mirror. I looked beautiful, darkly subtle eye shadow, shining lips, long luscious curled eye lashes, and of course dark curls of hair tumbling over my shoulders. Ellie seemed especially pleased with her handiwork. I could feel myself becoming aroused as Ellie said it was time to put my dress on. I said I'd like to just have a quick cigarette in the hope it might calm me down a little. She giggled a little but said of course.
I put the heels on so as not to ruin my stockings, and went downstairs to the back garden. The cool air helped me somewhat so I sat for a little longer, enjoying the afternoon sun. Eventually I made my way back inside and found that Ellie had put a dress and heels back on and was waiting in my room, reapplying her own lipstick. She turned and admired her handiwork on me once more before telling me once again that all that remained was the dress!
I hesitated, waiting for her to leave. She tutted at me and said, "Come now, you're not shy NOW are you? You've worn my panties for crying out loud!" she chuckled. With that I gently removed the dress from it's hangar and laid it out on the bed. With my back to her I slipped my robe off before gently stepping into the dress and pulling it up over my shoulders. Before I could reach back for the zip Ellie was there zipping me in.
She admired me as I stood. The only thing she could muster being, "Wow!"
"May I buy you a drink beautiful lady?" she smiled. I laughed and said maybe a small wine. I went downstairs and fetched the wine from the fridge. I was just just getting two glasses when she appeared in the doorway with two handbags and handed me one. "Not here sweetie!"
And with that she took my hand and led me to the front door. I was utterly terrified as we left the front door. The sun was beginning to set on a gorgeous autumn evening as we walked to her car. We drove to a small country pub nearby and together we went in. She ordered two small wines and we found a secluded corner in which to sit. We talked more and she complimented me on my feminine traits. I'd practiced heavily over the years. We got some smiles and waves from some men in the bar during our brief visit, I think we even turned the heads of a few ladies too. We chatted and before long we finished our wine and headed home for more.
As we sat at home drinking wine, and as is the way with alcohol the conversation began to turn a little racier. We spoke about sex very frankly. She asked if I'd dressed for anyone, if I'd been with a man, a woman, another cross dresser. She even asked if she turned me on which of course she did. As frank as our conversation was there was a turning point. As we opened the second bottle she asked if got turned on wearing her lingerie. Yes of course I did. Did anyone ever see me wearing her things. Yes a couple of times. I explained what happened. She asked me in detail what I wore. I told her about the last thing of hers I wore with someone, a red silk and lace basque with matching panties and flesh toned lace top stockings.
"Jess,"she said sheepishly. "I know that's what you wore."
"I'm sorry," I replied, thinking perhaps I'd said something wrong.
"No no, I know that's what you wore... And I'm wearing that right now. Hearing you talk about it and thinking about it is turning me on so much I could swear my pussy is on fire! For months I've been buying you things and it's been turning me on. Last week I went into your room and put on a pair of your panties. I got so turned on I came!"
I was shocked! Yet I decided to seize the opportunity. I took her hand and kissed her deeply before leading her upstairs. The guest bedroom had full length mirrors along one wall which covered a closet. I positioned her facing the mirrors as I stood behind her. I kissed her neck and pressed my body against hers. My hands tight on her hips, pulling her against me. She was moaning loudly. My hands began to explore her body, squeezing her firm breasts, then down and under her dress. My fingers found her panties saturated, seeking out her clit and within moments she was crying out in ecstasy. She pulled her dress off at the shoulders and pushed it down before reaching spinning to face me and kissing me. Her tongue hungrily found mine as she pulled at the zip to my dress. It fell to the ground and she stepped back to look at me, one hand inside her panties, the other firmly squeezing her own breasts.
She fell to her needs in front of me and tore my panties down, freeing my cock as she took it straight into her mouth. As she sucked hungrily she played with her pussy, moaning and cumming as forced my cock into her throat. She choked and fell back onto the floor. I pulled her up and threw her onto her hands and knees on the bed. Her perfect arse presented to me as I pulled her panties down before burying my face between her beautiful cheeks, my tongue seeking out her tight little hole as I fingered her dripping wet pussy. She was shaking uncontrollably and screaming with pleasure as she begged me to fuck her.
"Jess! Jess! Please I want your cock in my pussy! Please fuck me!" How can a girl refuse? I positioned myself behind her and lined my hard cock up with her wet hole. As I slid inside her she turned her head to watch me fuck her in the mirror. Her tight pussy spasmed around my length. I fucked her as hard as I could balanced on my high heels, her wetness covering me. I felt my orgasm building and pulled out before covering her sexy arse with come. As she slumped forward a spread those firm cheeks and began to lick up my cum. With my mouth full I turned her onto her back and as we locked together I kissed her deeply. She greedily swallowed the cum from my mouth and we lay that way for several minutes.
"Jess," she breathlessly said to me. "I think we should do this a lot more!"
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