Chapter 12
by
rivi
What different types of experience have you had ?
Strangers I have been grateful for
Sometimes joining with a stranger even if it turns out to be a ' quickie ' can be especially memorable because of what you did together or what he did to you was unusual .
In my early days of venturing out in a skirt I enjoyed putting thought into what to wear under it - getting prolongued erections simply from day-dreams of what scenarios might unfold with my selection . One titillating notion centred on wearing french knickers ( the kind where the legs flare out and come down for a couple of inches ) . I have always particularly liked the way the looseness of the legs feels free and I can feel the lacy fringe brushing my thigh and the floating nylon like a slip or skirt caressing my cock . But the strongest frisson comes from thinking how easy and accessible it makes me if an erect man were to reach under my skirt , then explore further towards my cock or ass .
Walking on the path around my favourite haunt a man appeared suddenly out of nowhere . He was young and , unlike me , dressed as a man . He stood in front of me and after a short moment of looking at each other we reached towards each others clothing . I unzipped him and his pants fell down . As I was pulling down his underpants he lifted my skirt . We found each other as stiff as could be and by co-ordinated instinct we drew his under and up my loose knickers where we caressed each other through the nylon while trying ( our cocks kept flopping ) to keep them touching each other .
This was so pleasurable ( a fantasy actually happening ! ) I barely had time to squeeze a messily large squirt of lubricant onto our aligned cocks . The added slipperiness **** a climax that was groaningly shared and the combined spurts of semen that wetted and darkened my knickers draped the nylon around our cocks as we let go with our hands .
We parted quickly , still without words , but I would like to think with gratitude - certainly on my side .
Sucking a man gives pleasure only by knowing you are pleasuring him , unless he is fondling you at the same time which is usually hindered by the positions you are in . Kneeling in front of him makes it impossible for him to reach where you would want to be touched . He can hold your head , and guys want to do that so they can pull you inwards to **** their cocks deeper in . While enjoying the humiliation of being fucked in the mouth ( and the aggressive pleasure he is showing by forcing himself deeper in you ) , the **** outbalances my enjoyment .
A 69 position where you can suck him and hope he toys with yours or teases your underwear is nice ( I don't particularly need reciprocation from his mouth , preferring he uses it to encourage me by words and otherwise his hands ) .
But the commonest expectation is to provide oral sex and the ground is often grubby enough that men don't want to lie down and anyway why shoudn't a sissy kneel on it - thats what submissive sissies will unhesitatingly do , right ? So a typical encounter in a stroll would be an approach and exchanges of confirmatory glances , perhaps a neutral observation about the weather , or often straight ' are you horny ' or ' what are you into '. Even these preliminaries are bypassed by men who are either making masturbation movements through their pants , or are showing you their cocks or , if seeing me in skirt and all , may simply communicate by gesture - that gesture being to nod down , or pull my head in the direction of their cock .
If a man does lie down for me , but doesn't encourage a 69 position then the most comfortable way to suck him is to lie stomach down with your head in his crotch . One man between whose legs I was lying wanted to watch me sucking him and had leaned forward to do so . He was saying things like ' that's a good girl ' and 'you like that don't you ' and these remarks always work on me so I was as far along as I had made him . Then he leaned forward a little further and grasped the back strap of the bra I was wearing and lightly pinged it . This was so erotic I climaxed in seconds .
Men can become casual if they frequent a place and become familiar with other regulars . While sitting on a convenient log one such approached me . While talking he would intermittently stroke me . He wanted his nipples touched , and I obliged ( " Oh that's good ). I was wearing pants and wanted him to see me and touch me through the panties I was wearing underneath , but as I lifted up , to be able to pull the pants down , he shushed me against doing so , pointing to a lurker whom he referred to by name . When I said " he just wants to watch " he indicated he did not want an observer . Yet shortly after a different man appeared ( unzipped ) whom , my companion informed me , had a huge cock ( penis size was evidently important for him and by this time I had got myself sufficiently undone that his delightful , but too intermittent , exploration , had enabled him to comment admiringly on my size , and behaviour ( "you'll come in time " ) .
He greeted the new arrival by name while casually reaching into the man's unzipped pants ( no underwear - a common and to me disgusting finding ) and extracting a fair sized circumcised penis which he drew into his mouth for several smacking sucks ) . During this time the lurker was still visible in the background . Mr unzipped and he then conversed about generalities ( I sat , ignored ) and after a while the former said he was going to look around , and departed . I had placed a tube of lubricant beside me which he queried then asked if I wanted to fuck him , and did I have a condom .( I didn't ) . Had I fucked a man . Was I married . His wife had recently died . He had fucked her up the ass and she had told him it was better for men , because of prostate massage . Men thought about sex every thirty seconds . It didn't matter which hole they stuck it in . Did my wife still fuck me . ( No ) . Thats why most guys were here . Liberated by these confidences I said I could put mine beween his cheeks . He said "you're fat ( meaning my penis ) I'd like that ". The Lurker had drifted in and out of view , but my companion had provided me with a burst of action and I had again ( during our conversation I had become limp ) become ready , and it seemed we were now uncaring about an observer . Then his phone rang ( " my daughter " ) and he took off !
What was the best encounter you ever had ?
- No further chapters
- Add a new chapter
Disable your Ad Blocker! Thanks :)
A CROSSDRESSING APPRENTICESHIP
How an unsuppressable need made me seek a place where I could express myself
Comments moved below the chapter.
Jump to comments
Comments