New Experiences With My Ex

Emma was my first girlfriend and as breakups go this was not too bad.  There were no major arguments, we simply drifted apart but had always remained friends.

That was 5 years ago and we would still message each other from time to time to see how the other was and exchange flirty comments.

I had been cross dressing for years before meeting Emma and to date she was the only person to see me wearing any kind of women's clothing.

After sex I had once managed to move a conversation about thongs into her suggesting I wear the one she had just taken off.  After putting it on I was rock hard and she was in hysterics.

I thought this could have been the point where I told her my deepest darkest secret but her reaction stopped me. It did though trigger a new element to my fetish as being laughed at turned me on.

With me hard the thong came off and we had sex again and from time to time afterwards she would show me lingerie in magazines and ask if she should buy it for me before laughing.

Anyway, one Saturday afternoon I was at home relaxing, drinking a few beers and watching tv when I got a message from Emma asking how I was and after a few messages she sent a screenshot of a bra and thong asking what I thought. The bra and front section of the thong were black leather but as an added bit of kink the sides and back of the thong were gold chain.

I replied telling her they were hot and that she should get the set adding a heart emoji to my message.

She replied asking what size I was along with a laughing face.

With my inhibitions lowered by the beer, I told her my size and that I had the perfect shoes to match.

"Ooohhh shoes, now we are talking babe" came quickly back followed by another that said "Show me."

Smiling to myself I went online and took a screenshot of a pair of Top Shop Supreme Extreme heels (7" platform heel which is very high for a 'high street' shop). I could have gone and taken a picture of the pair hidden away upstairs but I thought better of it at this point!

Sending it over with no comment there was a minute or so before she replied.

"Very sexy babe. I love mine" was the message that came with a picture of her outstretched leg and cocked foot adorned by those very shoes.

"Shame we are not the same size, would have loved to see you in these" came straight after with a heart emoji.

Having just finished beer number 5 I ran upstairs, grabbed mine from my closet and slipped them onto my feet before taking a picture of my leg and foot positioned in the same way.

Having added the photo to a message that said "Don't worry, I have a pair of my own" I sat for a moment, loving the feel of the shoes on my feet, contemplating what to do. I was just about to delete it when that bit of me that got turned on when she laughed at me must have taken over and my finger hit send instead of delete.

I would have instantly regretted what I had done but in seconds my phone showed an incoming video call from Emma.

Answering it I could see her shocked face and before I could say a word she told me to point the phone down at my feet. As I did I heard her squeal as she saw the shoes. Before she hung up she said "I'm so fucking wet right now, keep those heels on, I'm coming to yours" and the call was over without me having said a word.

It took Emma about 10 minutes to get to mine but it felt like an hour. I was just freshening up when I heard the roar of an engine outside on the driveway. Making my way downstairs in the heels wasnt easy but I did and opened the door to Emma's smiling face with her sporty blue convertible filling the scene behind her.

We both looked down at the same time and each saw that the other was wearing their Supreme Extreme 7" heels before Emma jumped forward and hugged me.

"You have no idea how happy I am" she said and I could feel myself getting hard against her. Obviously feeling it she looked up and said with a smirk "It looks like I'm not the only one who is happy" before winking and slipping her hand between us and into my sweats.

In the excitement of the afternoon I had completely forgotten that under my sweats and tshirt I was wearing matching lingerie (as I said I was relaxing at home and this was how I relaxed).

Emma clearly noticed as her hand brushed against my satin bikini style briefs.

Looking up and smiling she bit her lip in a sexy suggestive way before in an instant grabbing the sides of my sweats and dropping down to her knees taking them down with her. This left me just inside my house, stood with the door wide open and my leopard print women's underwear on show for anyone to see.

"Oh my god you are such a slut" she said laughing as she lifted my right foot and carefully pulled the one leg of my sweats over my shoe and off before doing the same with the other.

Standing up she circled behind me and ran her hand up my shaved leg before telling me I looked ridiculous with the tshirt on.

Pushing my back down slightly she started to roll it up at which point she saw the back of my matching leopard print bra.

"Take the tshirt off" she instructed and after doing so she slowly turned me all the way round, still there in the open doorway, until once again I was facing out into the road.

"This is so hot" she said slowly pushing my back down again and pushing herself up against my ass, whilst holding my hips.

As she did she said "God I wish I had brought some of my toys".

Facing forward I could now see a lady who lived opposite stood outside her door open mouthed as she stared across at me. I'm not sure how much she could actually see but panicked I pushed back into Emma with my ass and swung the door closed.

Turning to face her she immediately noticed that I was tenting out the front of my leopard print panties and laughed remarking "Clearly these are having the same effect as when you wore mine that one time" before slapping my ass and suggesting we go sit down.

Walking ahead of her I gave my best 'runway' walk and looked back over my shoulder to see her staring down at the heels as they clicked on my wooden floor. Getting to the sofa I span and motioned for her to sit and as she did I lowered myself onto the opposite end before she motioned for me to swing my legs up so that my feet rested on her thighs.

We talked about how long I had been dressing, why I did, what made me start and so on and all through this time she ran her hands up and down my legs and across my shoes.

It felt strange telling someone else about this side of my life and especially to the first girl who I had fallen in love with. I also told her about how it had felt when she had laughed when I tried on her thong and Emma could not stop apologising but did say that she had her own admission about that day.

"When I suggested you putting it on it was a joke but then when you slid it up your legs and I saw the string between your ass cheeks and how hard it made you it turned me on so much. I was just so surprised by my feelings though that I didnt know what to do or say so I thought to try and laugh it off. I am so sorry you felt that way though. I couldn't get over that feeling and that was one of the reasons why I ended things" she said leaning forward squeezing my bare thighs.

I asked her what she meant and that is when it was her turn to reveal her secret.

"After that I started looking online at cross dressing and forced fem sites and I wanted to find out more about that. From your reaction that day I didnt really think you would be interested, which is clearly ridiculous looking at you now."

"I have tried things with a couple of guys since you and some played along a bit but I never managed to get any into heels nevermind fuck me shoes like these".

Obviously I was annoyed but it was kind of funny and we had still got to this point now.

"So what now?" Emma said smiling and raising an eyebrow at me.

"I could show you the rest of my clothes and shoes" I said like an excited college girl getting ready for a night out with her friends.

"Or we could go shopping? I'm thinking that lingerie set I sent you a picture of earlier. Think how great it would be if we each bought a set.........and then wore it together later maybe" she said with a wicked look on her face that implied sex without actually saying it.

Asking where it was from I swung my legs onto the floor and stood up clearly showing my approval to the idea.

She told me it was from Ann Summers but her reply was a little drawn out as, with my back to her, I pulled out the edges of my leopard print panties and straightened them out over my toned, hairless ass. She followed up by telling me that I would be in so much trouble if we had been at her house which I guessed related to something she had said about toys a little earlier.

Grabbing my clothes from the hallway floor I made sure to bend at the waist and smiled as I heard Emma choke slightly.  After getting dressed Emma said we would be going back to hers later so told me to bring my shoes with me.

We walked out to the car and with me now in trainers she was a few inches taller, since she still had her heels on. Whilst I loved my heels it felt quite good to be next to her like this. She had worn heels when we were together but never anything this high.

We got into her car and started to drive chatting like we used to and whilst I felt a little nervous about what we were going to do it was not my first time shopping in person and given what was happening in the world I knew I would be wearing a mask and that there were very few people out shopping even now in the run up to Christmas.

Being December it was dark and we chatted for the 20 or so minute drive. Emma was making hints about my sexuality so I set her straight and told her that I had never been with a guy but that I did think what it would be like when I was dressed.

Arriving at the shopping centre Emma drove all the way up to the top floor of the car park that sat alongside the shops. Putting our masks on we walked the 30 metres to the entrance to the shops with her heels making that sexy sound on the concrete.

The automatic doors opened and walking past the public toilets I could see Ann Summers just ahead.

Taking my hand Emma held it and squeezed telling me that she had dreamed for years of doing something like this and she was so glad that it was with me.

We were still holding hands as we entered the shop and were met at the door by a girl of perhaps 22 or 23 who asked us to sanitize our hands. We did and she asked if there was anything specific we were looking for at which point Emma answered, apparently, for both of us.

"Me and boyfriend are after some matching lingerie" at which point she laughed before clarifying that she didnt mean a matching set but the same set for both of us! She then took out her phone and showed it to the girl who nodded and pointed us to a section of the store telling us where we could find it.

The girl then turned to me and said "We can help with bra fitting if you would like" but Emma was already pulling at my arm so I didnt get a chance to answer.

Finding the set easily enough we each picked our size and Emma said that she would pay for them after we had looked at a few more things but in truth nothing much different to things I already owned.

At the till a lady (probably late 30s) served us and pointed out to Emma that she had got 2 different sizes at which point she replied "Oh yes we have a set each".

Upon hearing this the lady looked me up and down and turning back to Emma said "Yes he does look the type" before then upselling us a couple of black fishnet dresses and stockings which were displayed on the counter. The stocking were a particularly good match due to the faux leather band at the top.

"Thank you, he is going to look so slutty in this" Emma said smiling and putting her arm over my shoulder as we turned and headed back out the door.

Once outside the shop she used her arm to turn me into her and she bent slightly before kissing me. Our lips met and then opened as her tongue entered my mouth, Emma clearly instigating and leading the kiss with me following. Her role as the alpha was further pushed home as her lips left my mouth and made their way down the side of my face and she began kissing my neck. At the same time as this I heard the bag drop from her other hand and felt as it then entered my sweats from behind and began squeezing my left ass cheek.

She stopped kissing me and taking her arm from my shoulder she picked up the bag and began to lead me towards the exit guiding me with the hand still gripping my ass. As we got nearer to the exit she began to speak.

"That was so hot but there is no way I can wait until we get back to mine, let's try these things on right now" motioning towards a baby change room next to the toilets with her head and eyes.

Having a quick look around I could see that there was hardly anyone around so I nodded and she pulled the door open letting me enter the room which was about 5 metres by 5 metres and had a baby change table, long shelf, a chair, a sink and a full length mirror on the wall. "Lock the door and wait here" she said pushing the Ann Summers bag into my hands and closing the door behind me.

Locking the door I began to take the things from the bag placing the two piles of clothes next to each other on the shelf. Unwrapping the tissue paper the room was filled with the intoxicating smell of leather, and I closed my eyes and took it in before hearing a gentle knock at the door.

Opening it a crack I could see that it was Emma and she has holding my high heels. "If you are going to dress like a slut you may as well go the whole way" she said laughing.

Opening the door so she could come in and then locking it behind her I turned and saw that she already had her heels off and was down to her underwear. Spotting the piles of lingerie she squealed and took off her remaining clothes leaving her stood naked in front of me. She must have noticed me staring as she shrugged her shoulders and said "Nothing you haven't seen before. Now hurry up and get yours off."

I began to strip and by the time I was naked (and rock hard) Emma was by now wearing the bra and thong with the gold chain at the back of the thong pulled between her ass cheeks. By the time I was where she had been she was sat on the chair wearing the fishnet dress over the top as she began to slide the stockings up her legs and her 7" heels back onto her feet.

When she was finished we switched places and I did the same as she just had. Looking up she had her back to me but I could see in the reflection of the mirror that she had the front of the dress pulled up and her hand pushed down the front of her thong working her fingers in a circular motion clearly enjoying the reflection of herself in the mirror.

Having finished getting dressed I stood behind her and seeing me come into her field of vision she pulled her hand away from her thong and reached up pulling my mask down before pushing two of her fingers into my mouth.

She tasted exactly as I remembered and I eagerly licked and sucked on them before she started to push them in and out of my mouth almost pretending that they were a cock and I was giving a blowjob.

"Let's save that until we get back to mine" she said pulling her fingers from my mouth following up with "shall we get out of here" as she went over and put her things into the Ann Summers bag.

"What do you mean" I said, a little confused, as she began putting my things in the bag as well. "We can't go outside like this".

"Of course we can, it's dark, there are not many people around and my car is less than a minute away."

What she said got me thinking as to whether I could actually do it but any time for consideration was short lived as she had now opened the door and had stepped out holding the bag containing all of our clothes.

Knowing that really I had no choice anyway I skipped to catch up with Emma (not easy in 7" heels) and grabbed her free hand, squeezing it tightly, as I got level with her.

Emma was always a little heavier than perhaps she 'should' have been for her height but she had a confidence that meant it wasnt an issue for her. Along with this confidence she also had amazing breasts and as she walked they bounced, barely contained by the leather bra.

As we stood in front of the automatic doors, waiting for them to open, through the glass we could see a guy walking towards us from the other side. "Ooohhh he's quite hot" Emma giggled. "I wonder which of us he will want to fuck".

As the doors finally opened we stepped outside into the cold air and the guy was now 10 metres or so away from us. He must have been 6'3" and from his frame clearly worked out. His hair was styled and you could tell from his walk that he was full of confidence. As we walked towards each other we had no indication of what he was thinking, as his mask covered his mouth, and I squeezed Emma's hand even tighter than before, nervous as to what might happen.

Walking directly in front of us, basically blocking our way, he opened by saying "Hello..........ladies" as his eyes went from our faces to our feet and back up again. "Where would you be going dressed like that" oozed from his lips in a smooth sexy way.

"Just back to mine" Emma replied. "Me and my boyfriend just got these and we couldn't wait until we got home to try them on".

"Very sexy" he said before asking Emma to spin for him, which she did. Getting his phone out he asked her to spin again and she silently complied as he filmed it.

"And you honey" he said looking to me.

Nervously I slowly span, conscious not to move too quickly so that I wouldn't spill out of the front of my thong. Stopping and now stood next to Emma again he panned his phone up and down the two of us.

After he stopped filming Emma asked if he would send it to her and he said that he would need her number. He asked her name and typed into his phone before handing it over Emma who then began typing away before giving it back.

"I have put my number and my boyfriend's in there. She is in there as Barbie, send us the footage and let us know if you ever want to play. She then stepped in close to him and squeezed his upper arm before telling me to do the same. As we stood either side of him he wrapped his arms over our shoulders and squeezed us both in and I could feel his biceps pressing into me through his hoodie.

"Oh wow you are strong" I said giggling.

Not saying a word he released us and stepped back unzipping his hoodie.

It was early evening in December and whilst I could not feel the cold, given the blood surging through my veins from the excitement, his nipples grew hard clearly visible through his tight white tshirt. The short sleeves also meant he could show us the bulging muscles on his arms.

"I work out" he said and Emma grabbed his arm to feel as he flexed.

"If you are grabbing a handful then I am doing the same" he said before grabbing her ass with his free hand.

"Come feel" Emma said turning to me.

"It's the same deal if you do" he said.

I stepped forward and Emma stepped away, letting me take her place. Putting both of my hands onto his arm I felt his hand cupping my left ass cheek and a finger tracing along the chain of my thong.

"Big and hard" I said turning to face him.

"You have no idea" he said. The words confidently dripping from his mouth.

"I'd love to see my boyfriend suck your cock" Emma blurted out.  Shocked I turned to her and she had a wicked smile across her face.  Turning back to him he smiled and asked where.

Grabbing our hands she pulled us across the carpark and I had to trot in my heels to keep up.  Getting to her car she pushed me into the gap between her car and the next before pushing him after me.  Squatting down she told me to do the same as she reached up and undid his jeans.  She pulled them down with the outline of his cock in his tight black boxers showing his excitement.