It had been a few weeks since I shared my crossdressing secret with my girlfriend Leanne and I'd been spending more time dressing up as a girl. My collection of girly clothing had grown and I'd ordered several more slutty outfits and sexy lingerie sets.
Leanne had helped me by giving advice, making sure I bought the right items and occasionally picking out a few things for herself. Outside of buying clothes together, we had retreated into our own routines again, spending more time alone, which gave me plenty of opportunities to dress up and play around.
She seemed happy but I had started to notice our sex life was suffering again. We still loved each other but the more I dressed en femme, the less I wanted to have sex with her.
Leanne had lost interest too and had begun to masturbate to compensate. A couple of times I'd walked in on her and caught her playing around with a dildo while she watched porn.
I didn't think much of it the first time, but after the second time, I realized how turned on she was getting, frigging her pussy with a large dildo while she watched other people have sex. She seemed to have a fetish for big cocks as I noticed that all the porn she watched featured men with humongous sized dicks.
It wasn't a problem for me. In fact, I kind of liked it and wondered about cock on many occasions myself. At least, in my fantasies when dressed as a girl and playing around. That was how I felt most satisfied now, sucking and riding fake cocks while my clitty leaked into my silk panties.
Leanne seemed to have completely lost interest in sex since our last encounter and I wondered if she would ever fuck me like that again. We talked about having sex but just never seem to get around to it, and to be honest, the only thing that turned me on was the thought of being fucked with a strap on.
It didn't take long before Leanne brought up the conversation again, starting one night while we were having dinner. We'd both had a few glasses of wine when she brought up the subject of sex.
"Baby, I wanted to talk to you about something," she said.
"Of course, honey. What is it?" I replied.
"So, you know how you opened up to me about your secret fantasy and your sexual kink? Well, I feel like I have something I would like to try and I'm not sure how you would feel about it?"
"Oh baby, you've been so supportive of me with my whole thing lately. You know I love you, what is it you want to try with me?" I asked innocently.
"Well," she paused, her eyes darting around the room unsure if she should continue before finally opening her mouth again. "Well, I want to try maybe having sex with another guy."
I looked back at her stunned and unable to talk for a moment. 'Fuck' I thought, 'Is she going to leave me for another guy?' I tried to reply with something supportive but I just began to sob instead. Quickly, she reached out, wrapping her arms around me desperately trying to comfort me.
"What's wrong, baby?" she asked.
"Are you leaving me for another man?" I replied looking up at her, tears rolling down my face.
"No! Of course not," she responded. "Not at all. I just..." she paused again. "I just think I want to try something new. It's fine, I don't have to. I won't."
I stopped her, putting my finger over her lips, "I understand, baby. I want you to be happy too," I said, wiping the tears away from my face.
"Would we share the experience?" I asked tentatively.
She looked down at me, a smile creeping across her face. "Of course, baby, I wouldn't want it any other way."
We finished off our wine and Leanne began searching sex sites for an appropriate candidate while I washed up the dishes. After a few minutes of searching and chatting to men online, she finally called me over excitedly.
"I think I've found someone, his name is Zach," she said, spinning the laptop around so I could see.
My jaw dropped as I saw his profile. His picture showed him bare-chested, showing off his huge muscles and toned physique. He had a chiseled jawline, gorgeous hair, and "come fuck me" dark, mysterious bedroom eyes. His skin tone was a light caramel color which made him look ambiguous, dark, and mysterious.
"What do you think?" Leanne asked inquisitively.
I tried to find the words, "Are you sure?" I asked, hoping she would change her mind and chose someone less attractive and threatening to my self-esteem.
"Yeah, he's definitely the kind of man I've fantasized about," she replied with a heavy emphasis on the word 'man'.
Now I was worried. He was so much better looking than me, so much more manly and confident. I suddenly felt really insecure, realizing that there was no comparison between us.
But, as I looked at the excitement on her face, I knew this was right. I loved Leanne and she deserved to be happy.
"Ok then," I replied, taking a deep breath as she snatched the laptop back and began frantically typing a reply message.
My stomach was in knots, watching her excitedly race upstairs and begin getting ready for her date. Apparently, he was on his way over and she was going to make sure she looked her best for him.
After a quick shower, she began putting on her sexiest lingerie set, complete with stockings and heels, quickly fixing her makeup and hair before deciding which dress to wear.
"Maybe you should dress up too, honey?" She said, searching through the closet. "He might like that?"
'She must have told him!' I thought, starting to panic.
She had almost finished getting ready, adding some more lipstick as she admired herself in the mirror. I sheepishly began to dress too, trying on some new lingerie to look as feminine as possible.
Leanne leaned over me as I sat in front of the vanity mirror. She took one look and picked up some brushes and began fixing my makeup. I guess she figured if someone was going to see me dressed like a girl, she wanted me to look at least passable, if not downright convincing!
Finally, I looked up, barely able to recognize myself in the mirror. She had done a perfect job on my make-up and was now pulling out a selection of dresses for me.
"Here, how about this one?" She said, handing me an extremely short suede micro dress. I quickly slipped it on and slid on a pair of high heels just moments before the doorbell rang.
"He's here!" She gleamed, her face lighting up as her eyes filled with lust.
Leanne hurried down the stairs to greet Zach while I nervously followed behind. As he stepped through the door, he politely kissed her on the cheek, running his hand down her hips softly.
He was even more handsome in person than in his profile picture and I could feel my jealously slowly turning into admiration.
Leanne escorted him to the front room and sat down next to him on the couch trying to make light conversation. I hung well back by the hallway at first, almost afraid to let him see me.
So far, Leanne was the only person that had seen me dressed like this, and I didn't know how anyone else would react.
Zach quickly picked up on my nervousness and leaned past Leanne, looking straight over at me. "And who is this precious little thing?" He asked charmingly.
Leanne and I both stared at each other vacantly. We'd never thought about a name before. Obviously, neither one of us wanted to use my birth name and before I could speak she responded spontaneously, "Tiffany!"
He smiled and then leaned in closer to Leanne, whispering something in her ear as he ran his fingers up her long sexy thighs.
She immediately turned to me, "Tiffany, baby, why don't you go get us some drinks. There's a nice bottle of Chardonnay in the fridge."
I followed out her request and went to fetch some glasses and the bottle of wine from the fridge before heading back down the hall. I had only been gone a few minutes, but apparently, this was more than enough time for the two of them to become firmly acquainted.
As I walked back into the front room I found them tightly embraced, his arms wrapped around her as he thrust his tongue down her throat, her body wriggling and writhing against him.
I placed the glasses down on the table and sat crossed-legged on an armchair opposite them, holding the bottle of wine.
Either they hadn't noticed I'd come back or they simply didn't care, because they continued to caress and explore each other right in front of me.
I began to sip straight from the bottle as I noticed what was about to happen, watching Leanne pull at his belt buckle, racing to unzip and remove his jeans.
I stared in silence as she began to pull down his jeans, slowly removing his boxer shorts and revealing his big stiff cock. He stood up, allowing her to remove his pants fully, staring down at her patiently.
From where I was sat, they appeared silhouetted in front of the netted curtains in the window, almost cinematic. The outline of their bodies creating an erotic scene in front of me as I continued to gaze.
Reaching out, he placed his hand on the side of her head, gently guiding her towards his yearning cock while she slowly opened her mouth to accommodate him.
My tiny clitty leaked into my silk panties as I listened to her moan and writhe over his cock, passionately sucking him slowly as she fondled his balls.
She looked so beautiful in the light, erotically performing fellatio on him. Her slim body arching back, perfectly accentuating her curves as his huge cock disappeared deep inside her throat.
I thought the sight of my girlfriend with another man would make me jealous, and in a way it did. But as I watched on, my mouth watered, no longer jealous, but more envious than anything else.
She made it look super sexy, sucking his cock so seductively, and at that moment I desperately wanted to be in her place. I barely noticed my hand slide under my dress and between my thighs, slowly fingering my aching hole as I watched in awe.