The Circle Ch. 01

Where to begin? I've been a crossdresser for almost as long as I can remember. I vividly remember my first pair of panties that would have been 1980's era string bikini but the panels were a fine striped lace. I loved wearing them I would wear them to bed I would wear them out under my shorts in public. There was always the thrill of not wanting to be caught which is of course code for wanting to be caught. Fair to say that I was hooked on that feeling and should have known then in my hick Australian city that I'd turn out to be a cross dressing bottom.

The years leading up to now have had mostly a vanilla time involving a little dressing and some toy play. The internet of course made it take off with new and wonderful way of giving myself the anal pleasure I desired and the feel to make me so hot I needed it. I felt often that my straight relationships were a lie as I longed for a girlfriend to take me roughly from behind. I had one girlfriend that embraced my fetish and bought me panties, lingerie and toys. Nothing like being forced to go to church but have a remote-control plug in your ass and the remote in your girlfriend's hand. I would always make sure that on those occasions I didn't wear lace panties as I often came in my pants. On those days my girlfriend would rail me with a strap on.

Later in our relationship we involved men giving me my first bisexual experiences and nothing really replaces that warm sensation of cum leaking out of your bottom into panties. Sadly, for me that relationship didn't last and ones that followed produced only toxicity. Toys on toilet seats and full dress up parties for one is all I had. Occasionally when I felt people getting close, I'd throw away my treasure trove of fun. Always swore I'd never do it again but here we are. Where are we now and what is the Circle?

Many years have passed and though I'm well passed my prime I'm still an active crossdresser and a devoted fan of receiving anal sex. I get my fun from toys though it's good enough for me no humiliation in a toy. I legit identify as a straight cross dresser that loves to get fucked. I say this as I don't find men attractive or appealing at all but love that now distant memory of a warm cock sliding passed my g-string on its way to my prostate.

I am now an empty nester and felt it was time to move house and have found myself in a very old (age wise) street surrounded by retirees (I still have a couple of decades until then). There is a lot of visual protection for me here and so I'm able to sit in my back garden dressed or water my plants from behind a perfectly placed wall in the front garden. For months I've been spending at least half my home time in dresses (some sexy some plain) in and out of my house. There's a thrill thinking that the neighbour will see me and be outraged.

A night in Spring is when I met the man I would come to know only as Daddy (he made it very clear that as a pillar of society I can't know his name - weird I know as spoilers, he lives next door). On this night I'd gotten new clothes in the mail and was wearing, if I'm honest, quite an uncomfortable gold sequined dress. I had a lovely white satin thong on, black stockings with a garter belt and patent leather Mary Janes (big size as I'm quite a big man). To top it off I have an exquisite vibrating butt plug in and I was edging myself with it sitting out of site in my back yard. I love that toy, it was the type to deliver what I've read is called a sissygasm.

Anyway, I'm sitting enjoying the light breeze run up my dress on to my reasonably large (8 inch) cock as my remote lover buzzed away earning every penny. It was the third night in a row and probably the 10th in a fortnight I'd been out there but the first all dolled up in gold sequins. Turns out I wasn't alone as my neighbour just called out "Looks like you're having fun." Jesus, I was mortified but also still horny as my remote boyfriend had me almost cumming at that moment (impeccable timing). I was caught, where would I run he lives next door so I said I am indeed (fuck it you're caught why not). "Fancy a chat?" he said. My instinct would usually be no thanks I'm sorry and run away but as I said I was edging.

I said "If you don't laugh you can come."

He hopped over the fence in a jiffy and was sitting at the table next to me. He was easy 60 and clearly sporting a hard on in his shorts as he looked me up and down. Now to be clear I'm no trap or sissy or trans I'm not trying to be a woman I just like the thrill of womens clothing and anal sex I mean I still have a beard. We talked about inane things for what seemed like hours but was probably 10 minutes. He saw the remote in my hand saw me twist it and then groan in pleasure and of course asked "What is that?", with a little smirk on his face.

I said "That controls my boyfriend for the night which I'm sitting on." At this point he got as brave as me and put his hand on my thigh just under the hem of the dress and I was thinking fuck you old man grab my cock or fuck off I want to cum. You might be thinking this is advancing pretty quickly, I think that's an understatement.

He told me that for weeks he's been spying on me in dresses, skirts, bathing suits and lingerie and jacking off while he works up the courage to talk to me. Today he's taken a Viagra and saw me writhing and thought this is my chance. He then said "I'm not going to jack you off or kiss you or suck your cock if that's what you're thinking, so don't get your hopes up." That was a downer, until he said with a devilish grin "But if you're keen I'd be up for fucking you up the ass right now." And Bingo was his name O.

I was so turned on at this stage I got dirty and said "Don't get my dress dirty daddy." God knows why I called him Daddy probably because he was old.

Now sadly for readers this wasn't a drawn out romantic love making session this was a fast and rough fuck. I stood, hitched up my dress but left my panties on. Daddy (who he came to be known as) pulled down his shorts to reveal what is in all honesty an underwhelming cock but who cares. A small cock is way better than a big toy. He roughly yanked the plug out and actually threw it to my garage ( I later found it ruined and broken - not cool) he said with some bravado "You won't be needing this." Daddy went to pull my panties down and I said no pull them to the side please. Since I was stretched and lubed and with him being not very big he pushed in to the hilt first go. No pain at all this cock could be a keeper.

For the next, lets be generous, 3 minutes he fucked me hard and fast like an 18 year old fucking for the first time in a panic hoping parents don't come in and ruin his fun. But I didn't care I was being fucked leaning over my outdoor table calling obscenities like fuck me daddy, breed me daddy, make me yours. He came hard but I didn't feel it having that insane thought of damn he used a condom (thankfully followed by that could have been stupid if he was bareback). When he finished he pulled out, removed his condom dropping it on the floor, pulled up his shorts and said "See you next time." Hmm I thought, that's a bit rough leaving me there but on the other hand what do you say after that? But, a next time? That's a stretch how likely is it that this happens again? Turns out it did happen again and spoilers it now happens a lot.

Lastly, it seems we had a voyeur and she enjoyed it a lot!