It certainly can

As mentioned I started to really dress up for my stroll appearances . A flouncy mid thigh length skirt in shocking pink ( I wasn't holding back on the sissy-fem presentation and that colour would stand out as I walked the paths that wound through undergrowth ). Panties , of course . Still a singlet - the bra and stockings lay in the future .

Just donning these after vaulting the fence gave me a very strong hard on . At the time I assumed that a male erection would seriously detract from my otherwise delectable femininity . I have since realised that men are even better aroused when seeing my cock sticking up under my dress . In the event it did not matter as I couldn't keep it from straining out when walking the inclines of the path and my first meet was anyway so beautifully accommadating . He was lovely because he clearly knew all about what sissies like - and all his actions were to give such as to give his newfound ' girl ' the time of her life - without getting anything for himself other than the gratification of watching me melt with pleasure under his ministrations - which started when he said ; " My , thats a pretty skirt ."

Just the right thing to say , and followed by an even better ; " Turn around so I can see it swing when you walk ".

These introductory remarks were alone sufficient for me to be on the threshold of ejaculating - which I'm sure he perfectly well knew - it is thrilling to feel someone knows he can deliberately excite you .

Then he smiled and patted the ground beside him. " Why don't you lie down and sunbathe - I can make sure you are in private " .

He spread a blanket and under the guise of steadying me as I stooped to it he placed his hands on either side of my waist ; " I'm glad you came along . I was looking for some company and you look real cute ". ( Adjusting the blanket to create a pillow ) " Make yourself comfortable ". He arranged me to lie on my back while he lay on his side propped up on an elbow . Slowly and gently he rested his hand on my knee . Slowly caressing my thigh his wrist caught the hem of my skirt as it moved upwards . I felt the coolness of the air as my panties began being exposed .

"Nice " . He pulled the skirt up to fully expose me , and with deiberate teasing care slid his finger upwards on the firm nylon bar of my burstingly erect penis. " I can see you like that ".

His finger lifted the elastic of one leg - enough for a slight breeze to enter so while I could't see from my recumbent position I knew I was exposed to his view .

He then lifted the waist elastic and let the panties descend to level with my hair ( trimmed to lower and more horizontal ) . I felt him gazing at me which made me squirm and raise up a sexual thrust . Without hurry he responded by a finger on the tip of my penis and gently stirring the natural lubricant I was leaking by this time ( I had already created a dark patch at the upper margin of my panties ) .

" Well I hardly need to help you , but anyway . "

( Shuffling something off to his side ) ; " Now lift your bum " He pulled my panties down further . Then I could feel the cold gel in the embrace of his warm hand and slow stretching from glans to base and back again began .

" You like that baby ? "

Me ; ( " I can't hold off ! "

(He spread my knees and raised them so my heels supported them bent ) ;

" I know that , just lie back so I can do you "

His timing was perfect . He had managed to use one of his ecstatic pulls to deposit a glob of gel further back on my ass , and as I writhed and gasped and squirted he got a finger in my anus . As I ejaculated he massaged inside me , side to side . I had never experienced an orgasm of such intensity , and as it collapsed all I could say was " How did you do that ? "

( Smiling ) " Glad you liked it ". And that was it . I went home and relived the memory many times . I've since learned this is sometimes called being ' punked ' and implies your futures status as being 'owned ' .

( I love it when men say stuff to me )

The next occasion I came in a blouse , ( I had still to buy a bra ) a skirt , garter belt and stockings . There was a different outcome .

I was picked out very quickly . My date was short , Italian looking and sounding . He lead me for a short distance from where I had been standing , ( soliciting ) . I'm not sure why - the patch of grass and weeds he indicated for me to lie on had less privacy than the one we had just vacated .

He also did something I couldn't make sense of , related to how I was dressed . As mentioned I was in womens' clothing , and not just the exterior - I had flaunted my panties for him ( and since he engaged me I could reasonably assume he drew the intended conclusion from that display ) - yet as he stooped over me he drew back my skirt and with a growl of disapproval and flipping a suspender strap said " what's all this ? " .

It didn't seem to be a rhetorical question and I mumbled a response of some sort - which when I look back on it might have been improved along the lines of ' its because it makes me feel like a girl , and I want to be used like a girl , and if looking at me makes your cock hard , then welcome and come right on in .'

My non-response seemed to get the niceties out of the way , and he had me lie on my stomach . The ground had a slight upward slope - which gave him some advantage in mounting me ( which is perhaps why he selected it for us ) - and after some shuffling I felt him undress me sufficiently to enter me . It was a short , passive copulation on my part - I didn't sense from his thrusts that there was much length - certainly no internal pleasure , nor the gratification of a long erect sliding entry which usually excites a man into ending it with a violent slapping thrust .

When he was done and had withdrawn from me I heard an exclamation of disgust and looked up to see him inspecting himself . He glanced angrily at me then picked up my discarded panties and wiped his cock clean .

At that stage the selfishness of my own urges had bypassed decency about getting shit on another man's penis . I hope the experience didn't put him off sissies permanently . (It wouldn't now - I take great pains to be as clean as any vagina when I anticipate I may be used as one ) .

This chapter illustrates that experiences - at least for a transvestite trying to allure strange men - can vary a lot . I can demonstrate that further by other vignettes which are not ( as has been the case so far ) in a strict time sequence , so the ' Apprenticeship ' is somewhat disjointed from here although I will try to present my sissy experiences in an overall progress through time .