Crossdressing With My Mami
- 4 years ago
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Crossdressing With My Girlfriend free porn video
My girlfriend and I had been dating for several years and our sex life had basically become non-existent. It had been at least a year since we last had sex, and probably another six months before that. The problem was, as much as I loved her, I had developed a different kind of attraction.
For some deep-rooted reason, I had grown a craving for ladies' clothing. Lingerie, stockings, high heels; all drove me crazy with lust. Eventually, this led to me dressing and wearing slutty outfits, gaining a sense of joy and femininity when I wore them.
Another few months went by without sex, but I had begun to experiment on my own. Dressing up when she was out and playing with her dildo's in secret. After several attempts, I began to enjoy the feeling of anal play and even managed to come a few times without stimulating my penis.
One afternoon, my girlfriend (Leanne) was out shopping. I thought I would be alone for hours so I dolled up, grabbed some lubricant, and one of her dildos, and settled down for some sexy alone time. Of course, I knew it was only a matter of time before I would get caught but that didn't lessen the shock when it actually happened.
Her face was a mixture of both surprise and confusion as she opened the bedroom door, finding me dressed in her bra and stockings, riding her dildo, and moaning like a girl. I leaped off the bed, covering my tiny penis, shaking with fear and shock. After a long silence, she spoke softly.
"Is this something you're into? It's ok, I'm not mad. Why didn't you tell me?"
I finally decided to open up to my girlfriend about my desires and newfound sexual kink. She was surprisingly supportive and offered to help me explore this side of myself.
"What would you like to try?" she said, smiling lovingly.
"I'd love to dress sexy and become more submissive. Maybe you could try fucking me?" I said, nervously.
"Ok, baby. I think I might enjoy being a bit more dominant in the relationship. What would we need?"
We sat down and talked about it for a while, writing a list of items we needed, and looking at outfits for me. She asked me what I wanted to do so I showed her some sissy porn and pegging; which she seemed to react well to, intrigued by the role reversals.
After ordering everything we needed, she finally put her arms around me, kissed me on the face, and stared right into my eyes.
"Thank you for telling me about your sissy side. I really love that you told me and I want to let you know that I'm looking forward to exploring it with you."
I looked back up at her, my eyes watery from her lovingly supportive words. "Thank you," I said sincerely.
A few days later, the first of the packages arrived; and we spent the next few days opening packages and inspecting everything we had ordered. By the weekend we were ready to explore my sissy side and I was really nervous, to say the least!
Leanne could tell I was getting scared as I was visibly shaking.
"It's ok baby," she said, "I want you to feel comfortable and in a supportive environment. I love you, baby!"
"Me too," I said, looking back into her loving eyes. "I want to pretend you are my lesbian partner."
She smiled and replied excitedly, "I love that suggestion. Do you want me to play a dominant role in this scenario?"
"Yes, baby," I replied, "I want to feel sexy and slutty. I want you to treat me like your property."
Leanne smiled back, "I really like this lingerie. Why don't we go and make you feel a bit more girly first?" Taking my hand and leading me to the bathroom.
As I stripped naked, Leanne began to spray some hair removal cream into her hands, rubbing her fingers gently over my chest and working her way down. I nervously waited for the cream to take effect and then stepped inside the shower. The warm water felt so relaxing as it washed away the hair leaving me soft and smooth all over.
Leanne handed me a towel and helped dry me off, wrapping the towel around me chest ad tucking it in at the front. She asked me to follow her back to the bedroom and told me to sit down in front of the vanity mirror. I did as instructed and sat down avoiding eye contact.
I sat perfectly still as she carefully began applying foundation to my face. Not moving and staring into space, in a dreamlike state as she continued, applying mascara, eyeliner, and lip gloss.
After several minutes she stopped, grabbed a wig, and adjusting it onto my head, combing my hair before standing back.
"Hey, baby, look up, see how beautiful you are!" she said proudly with an arrogant smile on her face.
I lifted my head and looked up, barely able to recognize myself. 'Oh my god,' I thought. "I look like a real girl!" I said out loud.
"My sexy girl!" Leanne proclaimed, a grin spreading across her face.
"Let's get you dressed up then!"
I stood up and followed her to the bed sheepishly. I was desperate to try on all my new lingerie and see how it felt against my soft skin. The thought had kept me on edge for days, just waiting for this moment, relishing every second as I picked up my silk thong and brassiere, feeling the soft material in my fingers.
Slowly stepping into the thong I tucked my tiny penis back so only a small bulge could be seen and slipped them on over my bum. Leanne helped me by sliding the bra on over my arms, clipping it together behind me as I stared back in the full-length mirror.
"Here," she said, passing me a tight pink lycra mini dress. "This is yours, I bought a matching one in black for me."
She pulled her dress over her head and down her slender body, shuffling in the tight dress before helping me with mine, then stood behind me.
"You look so fucking hot baby!" she said, kissing the back of my neck and sending shivers down my spine. "You're ass looks amazing in that dress."
I looked back at her, a thrill running through me as I admired our sexy feminine outlines in the reflection.
"I'm so excited to try this with you. Do you want to play for a bit first?" she asked tenderly stroking the hair out of my face.
"Whatever you want baby, I'm all yours," I replied softly.
Without warning she grabbed my shoulders, spinning me around in my heels and pushing me onto the bed.
"I want you to eat my pussy, slut!" she said, lifting her tight dress up over her hips and pulling her thong to the side.
'Oh fuck,' I thought, she's already getting into the role. My eyes lit up.
"Yes mistress," I replied timidly.
She climbed on top of me, straddling my face and forcefully grinding her pussy onto my mouth. She was already wet as I began to explore her with my tongue, licking her clit and listening to her soft moans.
She looked down curiously, staring into my eyes as she began to fuck my face harder and faster, suffocating me with her soaking pussy. "Yes, that's it!" She screamed, "eat that pussy sissy!"
Her words sent shocks of excitement through me, motivating me to lick her like never before, engulfing her pussy with my mouth and sucking on her clitty as my tongue darted desperately around her labia. Her moans became louder, reaching down and grabbing hold of my head as she continued to grind her pussy harder onto my face.
For the next twenty minutes or so I lapped up at her moist pussy, lavishly running my tongue inside her pink hole, sucking vigorously on her clitoris. Her moans became louder and more intense as she clung onto my head, riding my face as she used my mouth to get herself off.
Suddenly she let out a loud scream, quivering and leaning back, arching her gorgeous body as she moaned heavily. "I'm going to come on your face!" she yelled, squirting all over me, making me wince as I tried to avoid getting her pussy juices in my eyes.
She had never done that before, at least not with me and it was incredible to watch her as she fell back shaking and convulsing from an intense orgasm. I tried to dry my face with my hands, now able to move again as she rolled off me and onto the mattress. Her breath was still heavy and panting.
"Are you ok, baby?" I asked inquisitively.
"Yes, honey," she replied. "I haven't come like that in years."
For some reason I started picturing her with her ex-boyfriend, getting fucked and squirting all over his cock. I knew she had come like this once before with him and I had to admit it, the thought aroused me.
"Your turn honey," she said, catching her breath and stepping off the bed.
She walked over to the dresser and began to slip on a black harness, adjusting the straps and attaching the 8-inch realist black dildo we had purchased. She knew I had a fetish for BBC and was happy to indulge in my fantasy.
"How do I look?" She said, turning around and rocking her hips, making the dildo shake up and down.
"So sexy, baby!" I replied.
"Good, then bend over slut, I'm going to make you my bitch." She giggled, reassuringly, grabbing a bottle of lube and dripping it onto her cock.
I rolled over on the bed, arching my back and lifting my bum into the air as she approached me from behind, lifting my tight dress up over my ass. I was so loose and ready that I barely noticed her gently slide the tip inside me, grabbing my hips tightly and thrusting a few inches deeper.
'Oh fuck,' I thought, 'that feels incredible!'
She began to push further, four, five, then six inches deep inside me, rocking her hips as I groaned in pleasure.
"Mmm, you like my big black cock inside you?" she asked rhetorically.
I just moaned into the mattress, gripping onto the bedsheets with my fingernails as she continued to fuck me.
"Yeah, you love getting fucked by my big cock don't you baby!" She yelled, speeding up, gripping my hips harder as she eagerly tried to push the dildo further into my tight ass.
I lifted my head gasping for breath, whimpering like a little girl as I begged her to fuck me, "Please, mistress, please. Fuck me like a girl!"
Grabbing me tighter, she began pumping her cock faster inside me, slamming her hips against my cheeks, making a slapping sound that echoed around the bedroom. For several minutes she continued her motion, talking dirty to me, degrading me as she fucked me with her strap on, ramming all eight inches inside me.
I could feel my tiny cock rubbing against the silk bedsheets and my balls clench as I let out a pathetic girly moan. The feeling was overwhelming causing an involuntary spasm in my tiny cock and forcing me to shoot streams of come through my thong and all over the bed.
Leanne had obviously hit my g-spot in just the right way, making me shudder and moan as I emptied my balls, creating a wet patch on the bed. She could tell I was coming and pushed the entire dildo into my ass, holding her whole weight on top of my body, waiting for me to finish my orgasm.
After a few intense seconds, I finally stopped shaking.
"Aww, baby, did that feel good?" Leanne asked.
"Baby, that was so good, thank you," I replied.
Leanne shifted her body weight, making me whimper as she slowly eased the dildo out of my ass. She walked over to the dresser, removing the strap on and undoing the harness as I lay still on the bed admiring her.
"I love you, baby," I said, watching her undress.
"I know, honey," she said, faking a smile and grabbing a towel as she headed to the bathroom, leaving me alone with my thoughts.
'I do love her,' I thought; 'and that felt so good! I wish I could fuck her as good as she fucked me. If only I could satisfy her like a real man!' I thought to myself.
To be continued...
Eisley
- 19.03.2020
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