Old Friends New Benefits

Old friends - new benefits.

This is a story about long time friends where one of the men decides to try to change to friends-with-benefits by dressing up as a female alter ego. It involves consensual relations between a man and a willing crossdresser. Read on, or don't. Positive comments appreciated.

My preparations for tonight started a couple days ago - shaving my body, legs, arms, chest, groin - leaving a patch above my cock but smooth everywhere else. Planning the menu, finding some clothes that masked as much masculinity as possible. Then shaving again yesterday, and finally one last round with the razor today. The addition of lotion smoothed my skin. I decided against taking care of my hardon and wore some specially prepared panties instead.

I slid my gray wool skirt up over my garter supported hose and tried to smooth the lines, a slight bulge was the best I could accomplish. I added a bra, 38C to fit my chest, the C was provided by a bag made from cut up hose with a couple cups of rice for each side.

A few minutes to arrange to the best of my ability before donning a cream-colored blouse that started life with long sleeves, but I modified to a 3/4 length to give my shoulders a bit more room. A shoulder length dirty blond wig was my crown.

Ding Dong. Welp, showtime. I was nervous, excited, curious, aroused. My crossdressing had always been a me thing only - this would be the first time anyone than the person in the mirror saw me dressed as a woman. A deep breath, a smile, and I opened the door. Tits up!

Alex almost dropped the 6 pack he brought for the evening when he saw me in the doorway. 'Jeremy?' he asked tentatively.

'Jeremy had a last-minute change of plans. I'm Amber his... cousin. Jeremy knew how much you wanted to watch the game and asked me to be a gracious hostess in his place. Interested in watching the game with me?'

He tentatively entered and presented me with the 6-pack offering, adding 'I thought a couple years ago when we...'

I cut him off with 'Jeremy mentioned you two tried to hook up a couple years ago - my guess is you just needed a lady around.'

'Are you saying you're a lady?' he inquired, becoming more relaxed with the situation.

'I can be a lot of things.' I added with as coy a smile as I could muster.

He stepped in and offered me a beer.

I declined saying 'I was hoping for something a bit... harder'. As I reached my arms around his neck, pulling us closer. Alex didn't recoil with my provocative suggestion, which I took as a good sign.

'I'll put this in the fridge then' he said, wrapping his arms around my waist, pulling us even closer.

'And I'll get the whiskey' I said, our mouths nearly touching.

We released our embrace; I poured a double measure of Makers in one glass - and filled another with coke. Alex gave me a puzzled look, questioning my bartending skills. I held out both glasses. 'You take a sip of one, I take from the other, and then we mix' I said, puckering my lips into a kiss.

He took the whiskey and took a sip and I the coke. I put my arms around his neck and our mouths reached for each other. We used our tongues to mix the whiskey and coke in each other's mouths. I could feel his arousal pushing into my own.

I hopped on the counter and spread my legs invitingly. Alex stepped closer, rubbing his hands on my knees and started sliding his hands up my thighs. I put my arms around his neck, encouraging him to close the gap between us. His hands stopped when they reached the bottom of my panties, but his lips continued. This time our tongues explored each other's mouth without the excuse of mixing a drink.

We broke our kiss. I took a heavy drink from the whisky - he took a modest sip of the coke and we resumed another kiss-mix as I wrapped my legs around his thigs and pulled his groin into my panty covered hardon.

'You mix a strong drink'.

'I'm getting a taste for the hard stuff' I replied, grinding our groins into each other.

The bell on the oven broke our trance- I uncovered the lasagna for the final 30 minutes baking. I knelt to a cabinet to grab a trivet; Alex took the opportunity to step directly in front of me, his legs boxing me into the corner of my kitchen - his crotch at my eye level. I put the trivet on the counter, looked up and our eyes locked. Without breaking our gaze, I unfastened his belt, then his jeans and zipper, pulling his pants to his knees. I reached one hand up the leg of his boxers, his hardness was impressive as I gently stroked the underside of his dick with my thumb. My mouth joined the party by breathing lustily on his shaft through his underwear. I pulled the waistband of his underwear down, exposing his head. I opened my mouth and directed his dick to my opening. My mouth took sliding his head and shaft in, allowing one hand to slide down, holding his balls while my fingers caressed his taint. My other hand was working the base of his shaft, keeping everything stable for my mouth to maintain positive contact.

I closed my eyes and concentrated on his cock. I had been practicing on some dildos for years, but they were nothing like the texture, heat and feel of the real thing. I found the real thing an appreciated improvement. I focused my mouth on his helmet, running my tongue under the ridge while working my lips on the spongy tip.

While massaging his taint with one hand - and the base of his cock with the other, I started Frenching my way down the spongy underside of his hardon. When I worked my down to his ball sac I looked up, our eyes met, he reached down and caressed my cheek while I worked on giving him a hickey where his shaft met his balls.

His gentle encouragement was what I needed to see how much of his manhood I could consume. I licked my way up his shaft to the tip - squeezed the base of his shaft, and took about half his shaft into my mouth, no problem. I left a generous amount of spit on his shaft, took a breath, released his shaft with my hand, and took his tip into my throat, suppressing a gag.

I didn't take long before I felt his balls tightening - his orgasm getting closer. I glanced up, his eyes were closed as he bit his lip. I knew there was no stopping the inevitable at this point. I started bobbing my head up and down his shaft, why in unison one hand aggressively rubbed is taint and the other hand masturbated the base of his cock.

My ministrations were rewarded by a groan and a powerful spurt into my willing mouth. I instinctively swallowed each spasm, the final couple spasms I held in my mouth. I suckled gently a couple times as I encouraged the last of his cum out of his shaft, and into my mouth. When he had fully softened, I released his dick and used my hands to replace his dick in his undies. I gave him a gentle kiss through his boxers and looked up - our gazes locking on each other again. I smiled as I pulled up his pants and replaced his zipper and belt.

I could still taste the remnants of his orgasm in my mouth as I took a long draw from the glass of Makers. He took some of the coke and we leaned into each other for another mixed drink.

'That was incredible,' he mused, pulling me close to him.

'I enjoyed it as well,' I said taking another sip of Makers.

The oven rang again, signaling our dinner was ready.

Should Alex and Amber continue their new friendship?