So when Ellie temporarily moved abroad as part of a six-month company transfer, she decided to let Mel stay in the house rather than sort something else as she would be moving back. The other thing that left was seeing her constantly to fill my fantasy of images of her. I don’t think I was the first guy to fuck their girlfriend and think of their mum asleep down the hall. Ellie was mid-forties but with a body of half her age. Her legs went on for days and her assets were perfect in my eyes, without a word of a lie, she was Nigella Lawson with dark blonde hair. I initially didn’t think she knew how gorgeous she was, she stayed single after Mel’s dad moved out years before – no idea why.
The first time I stayed over at Mel’s after Ellie had left was surreal, I felt like something was missing. We of course made up for not having her mum around by having sex in every possible area of the flat over the weekend. It was glorious and turned into a much more exploratory time than I first guessed. It was the first time Mel properly moaned during sex, the pinnacle was when I had her hard up against the hallway wall. I’d lifted her up and she was completely off the floor, her 5ft slim frame suspended on my rock solid cock, her tiny tits shaking in time with her moans. “OMG DON’T STOP,” she moaned breathlessly. I grinned and paused my rhythmic thrusting and lifted her slightly higher so only the tip of my cock brushed against her soaking, pulsating lips. “DON’T YOU DARE STOP! FUCK ME NOOWWWWWW,” she growled in a husky voice as I brought her back down onto my solid cock and took a tit between my lips. Then her voice broke off even though she was mouthing something else, all I heard was a whine, but it built into a sound only heard when watching porn “Uh-huh, uh-huh, yea baby, UH HUH UH HUH FUCK ME GOOD!”
Her eyes rolled back, her head looking to the roof, her back and arse smacking the wall as I felt myself getting closer. All I could picture was Ellie, Ellie getting pounded and moaning at me. “Oh! I’m gonna c…”. I couldn’t finish as I finished myself. And by the shaking and tightness, the silent sounds Mel looked to be making, I’d finished her as well. Hot cum filled the condom, her cunt pulling every last drop out of me as her waves started to ease. I turned and carried her through to the lounge, dropping her gently onto the sofa while making sure I didn’t make a mess. We fell asleep and the next thing I knew, I woke in the early morning.
I cleaned myself up and as I walked back to the lounge, I opened Ellie’s bedroom door out of curiosity. It was immaculate, like a showroom or out of a home styling magazine. She had great taste and took pride in her home, even though she wouldn’t be using it. My eye caught a photograph of her on the nightstand, she was posing with what I presumed was a work colleague. The photo was from an awards ceremony in the industry she was in so both ladies were wearing elegant evening gowns, all dolled up. As ever, Ellie was stunning, she wore the fuck out the dress, with a slit up her left leg, exposing to almost her waist, he stilettos finishing the look. I turned to leave and caught sight of those exact heels, along with others at the bottom of her closet. Without thinking, I stepped closer, pulled one shoe out and slipped a foot in. “What the fuck?” I mouthed to myself. I felt my cock start to stir.
I heard Mel stirring next door so I put the shoe back, quietly closed the bedroom door, and walked through. “Mmm someone is happy to see me” so purred, licking her lips and staring at my cock that grew by the second. I smirked and walked over to her waiting mouth.
Over the next few days, I couldn’t get the thought out of my head of why I put on the shoe, “Am I gay? A sissy?” I just knew it felt good and I wanted to do it again.
As luck would have it, Mel went on a university ski trip and I decided to take advantage of the empty house. I knew there was the stereotypical spare key under a plant pot so I found that and let myself in. I shivered when I locked the door from the inside, not because it was cold but from something else. I took my trainers and jacket off and walked quietly along the hall to Ellie’s room. “Why am I tiptoeing?!” I said out loud to myself, laughing at the ridiculousness of the situation.
Opening the door, my eyes landed on the photo again. “Fuck me you’re gorgeous,” I said to photo Ellie. I turned and saw the heels, and took the time to investigate what else filled the wardrobe. I knew she was in some form of HR/management type role in a classic corporate workplace so smart work attire was her staple but surprisingly I rarely saw Ellie in “work mode”. My fantasies went into overdrive, there were smart tailored dresses and skirts with blouses and matching blazers packing one half of the closet, with the rest being filled with dresses like the one in the photograph, along with casual clothes all in some form of order. The bottom was all forms of footwear, with a substantial amount of heels, from pumps and kitten heels to ridiculous stilettos.
As I looked through the wardrobe I could feel myself getting hard, I looked at the heels again. Picking one up, I sat on the edge of the bed and stroked the thin heel, along the side to the pointed tip, and then again slipped my foot in. “I’m a crossdresser?” I said to myself coming to a relieving realisation that I enjoyed this, my cock growing hard. I took the other heel, and with both my feet encased I took a breath in and stood up. I gasped, it felt so fucking good. There was a mirror to the side and I looked myself up and down, the top and jeans topped off by a pair of heels. “This won’t do, it clashes” I giggled to myself. I’d already decided I was all in.
Click clack click. “What the…?” The sound caught me off guard until I realised I was making the sound while walking across the wooden panel flooring in the heels. My cock swelled inside my boxers. This was amazing. I sat on the bed again and took off the heels then stripped naked, the pre-cum dripping from the tip of the rock solid cock. I wandered around the room, enjoying the free feeling of being naked in Ellie’s room, the anticipation made my heart race, I was so excited. I was about the grab the dress from the photograph when I realised my mistake, I had no lingerie! I looked around and started opening drawers, there were neatly folded piles of jeans, sportswear, and tops of various forms, I admired her desire to keep everything tidy. I opened the next dresser and gasped again jackpot.
Each drawer in the unit was packed full of lingerie, one drawer was clearly “daily” panties, then socks, another had nothing but bras and similar tops, then nightdresses, and the bottom drawer was deep with tights. I put my hand in to pull out a few then noticed the suspended belts underneath. “Oh, Ellie…” I moaned. I didn’t know where to start and I kept unconsciously stroking my cock. I need a release. I picked up a simple black lace thong and matching bra, slipped them on and grabbed the heels again. Pulling them on again, I gazed at the open rack of clothes, in awe of the gorgeous pieces I could choose from. I decided to keep it simple, knowing/hoping I could do this again. I pulled out a plain LBD. “Let’s hope we’re similar sizes babe!” I said to myself, knowing I would fit in. I was a slim lad, not skin and bones but not stocky. I stepped into the dress with ease and pulled up the zip. I stepped back and deliberately paced about in the heels, enjoying the sound they made. I walked into the hallway, slightly paused as if to make sure the coast was clear. Laughing to myself I strutted around the flat, feeling the dress move against my body, the hem pulled across my thighs, the thong set in my bottom, and the heels force my legs to elongate and wiggle my hips.
My cock was begging me to do something so I gave in and went to the toilet. I wanted to enjoy myself a moment of clarity made me make sure I wasn’t going to make a mess. I sat down, hoisted up “my” dress, pulled my cock out of “my” thong and pumped myself fast. I didn’t last more than ten seconds and I erupted so fast, I spurted a string of hot cum across the bathroom into the shower screen, “Ugh” I moaned in pleasure. “Mmmm, definitely a crossdresser then!”
