Dressing for [M]y flat[m]ate to help him through lockdown

Hi all

Long time no posting.

So, Covid sucks, right? Well so do I. Since the U.K. lockdown started last year I’ve had to do my best to cope with basically being stuck in my flat all the time. My flat mate has a suppressed immune system so we’ve had to be super careful to make sure he doesn’t get infected.

Even when things were relaxed slightly last summer we didn’t go out much, the risk was too great to him if one of us caught it.

We got into a rhythm of living effectively through a pandemic. I started to go on cams to make a little extra money and give myself an excuse to dress as a girl and be a slut again. My flat mate, Gary (not his real name) knows that I’m bi, knows I’m a cross dresser and he’s cool with it. He’s seen me plenty of times as a fishy girl and he doesn’t bat an eyelid.

Around September last year his girlfriend broke up with him. They’d been having problems before the pandemic but after 6 months of not seeing each other she threw in the towel. He was crushed. He was really upset and fell into a bit of a depression.

For his birthday in the October I wanted to do something nice for him. He was still feeling low the weight of the world on his shoulders so I decided to give him a treat.

In the evening when he finished work I told him I had a present for him, I just had to wrap it. I scurried to my room and got ready. I wore stockings, heels, a small thong, a lace bra and a slinky little cocktail dress. I put my breast forms in to give me some shape, styled my hair and did a full face of makeup. I also stuck a little bow onto the cleavage of the dress just to show that I was his present.

When I walked back into the living room his eyes went wide. He stared at me completely unsure of what to do.

“Hi, I’m amber, I hear it’s someone’s birthday” I said in my femme voice to him. I tried to make it so he didn’t see me as his flat mate, but as a cute girl. It worked and he played along, addressing me as Amber.

I got on my knees in front of him, “I hear someone’s been lonely. Would you like me to keep you company?” He nodded and I took it as my cue to open his pants.

His cock is lovely. Not massive, but not small. It’s a nice straight shaft with a good sized head on it. I kissed it gently then took it in my mouth. He moaned softly as my head bounced up and down on his lap

I told him I would do whatever he wanted. He told me to strip for him. I put on some music and did a striptease, slowly taking my dress off and parading around in my lingerie and heels. He told me to lose the lingerie, so I did, standing naked, my body smooth and my small cock rigid in front of my flat mate for the first time ever. He asked if he could fuck me, I said he absolutely could.

I went to the bathroom and retrieved my lube. I made a show of spreading it around my asshole, then slathering it on his cock. I asked where he wanted me and he told me to ride him. I pushed him back on the sofa and straddled him, lowering my hips down onto him. He moaned as I teased the head of his cock with my asshole, then he did something I didn’t expect, he grabbed my hips and started to force me down onto it. The lube helped but I expected a little more time to get acclimated to the cock so it hurt to suddenly have one forced into me, but he loved it.

I grinned through the pain until my asshole relaxed a bit. I rode him slowly at first until he started to take control and pick up the pace. Before long he was fucking me like I owed him money.

He asked if we could change position. I expected he wanted to go doggy, but no he moved me onto my back, then he put my legs over his shoulders and he entered me. Fuck, it felt so good. He’s a big guy and he made me feel so small and helpless. He fucked me like a piece of meat. Even when I started to cum and covered myself he kept going.

It didn’t take long for me to feel his cock swelling “fill me birthday boy” I said. He grunted and groaned, depositing a huge amount of cum in my asshole.

He softened down then slipped out of me. He gave me a single kiss on the lips and thanked me. I told him he could have Amber any time he wanted, he just needed to ask.

He hasn’t asked for her since. Things have remained normal for us since too. I think “Amber” helped him keep me separate from the dressed up CD slut he fucked.

Either way, he was much happier after that night. He started to get back to his old self.

Source: reddit.com/r/gonewildstories/comments/mdrx0v/dressing_for_my_flatmate_to_help_him_through