I sat next to Josh as Deborah had suggested. I turned to him and we smiled .
I wasn't sure what she was expecting because although I loved her playing with my bottom and I had wardrobes full of girly clothes I'd never admitted to being gay or even bi.
Chatting with Josh over dinner looking into his soft brown eyes I just knew he was a submissive bottom like me.
He was a big guy with man boobs and a belly, something I really liked but, I'd always fantasised about a much older more rugged man. Perhaps even a little pervy the sort that might hang around public toilets.
There was quite a few toilets near where I lived and I found myself drawn to them. I loved the smell and the anticipation when walking in, wondering if there would be a man inside.
It was a nervous excitement and a feeling of vulnerability. I never did anything but I enjoyed reading the stories on the walls and peeping through the holes.
Deborah went to make coffee and Josh turned to me.
"Are you a bottom", he asked.
I explained that I'd never been with a man but if I did then yes I'd be a bottom.
He laughed and said he didn't think Deborah understood that part. I agreed that she probably thought a gay man was a gay man.
I told him he was very nice but if I was going to give myself to a man I wanted an older alpha male and he agreed.
Deborah came back in with the coffee's. Josh explained that he would drink up and then go.
I could see Deborah was disappointed, I think she expected us to do something.
When Josh left, I explained about bottoms and tops, alphas and betas. To my surprise Deborah, although experienced with men had no idea about all this.
Oh well she said changing the subject have you seen this mail order catalogue I've got.
She passed me this A5 size glossy brochure for a local marital aid shop as they were called back then.
She said she'd circled some things inside that she might buy for me.
I looked through and found a set of toys circled. A vibrating butt plug, love egg and a vibrating cock ring. It looked cheap but fun.
I carried on thumbing through the pages. My eyes lit up when I saw she had circled a 6 inch strap-on. Again it was a cheap one with knicker elastic for straps.
She said she was going to order them and I thought it was a great idea.
She came and sat by me and put her hand between my legs. It made me jump, it always did but she told to calm down she wasn't expecting me to perform - I was relieved.
She told me she was disappointed that Josh and I didn't put on a show for her.
I said that actually there was something in the catalogue two sissies like Josh and I would love. She passed me the catalogue and asked me to show her.
I thumbed through to the dildo section and showed her the double dong.
She laughed and asked why I was blushing and I said because I love the idea of Josh and I getting on all fours bum to bum with that up our arses.
She asked if she should order that as well and I said,
"Yes you can do" 
We were both feeling frisky so she took my hand and lead me to the bedroom.
She told me she was going to show me how she wanted to be fucked. She made me swap clothes. I put on her peach skirt and blouse and she put on my shirt and jeans.
Then she smirked and told me to go and get the cucumber from the fridge. Like a good little sissy I did as I was told.
Deborah directed me to get on all fours on the bed with my bum in the air.
I loved this position it made me feel so vulnerable.
She put the cucumber in her pussy with a good six inches poking out through the fly of my jeans.
She approached me rubbing the cold cucumber up and down my ass crack.
"Come on baby", she said, "Work for it".
I pushed back on her rubbing my ass crack up and down the cucumber.
She told me to show her my rosebud so I reached around and held my ass cheeks apart.
She pushed the cucumber against my hole but I was nowhere near ready to take such a thick cucumber up my ass.
She kept pushing and it made me cum a bit. She toyed with my willy and rubbed some cum into my bum along with some spit and slowly she opened me up.
It felt so good when it popped inside me and I pushed back on her while trying to tweak my nipples.
Slowly I got wetter and it went deeper inside me. All the time cum was dripping from my cock onto the sheets. Then finally I exploded and collapsed down on the bed.
Deborah held the cucumber right by my face it was wet and glistening.
"Lick it, I dare you"
I looked at her and smirked, she was a dirty bitch and I loved that about her.
I knew I was clean, I douched everyday.
I gingerly licked it and thought it tasted a bit like cum.
"Suck it like this you wussy", she said closing her mouth around the cucumber and giving it a good suck.
We took either end into our mouths like it was a double dong and sucked on it. Deborah easily took the biggest length it was like she had no gag reflex.
After we got into bed for a cuddle but I hadn't finished and Deborah pushed me under the bedclothes to finish her off which I duly did.
I lay there thinking about the double dong, wondering if Josh was up for a bit of fun. Although I really wanted a hunky alpha male the idea of two sissies having some fun did appeal to me.  |
