A Fateful Winter Stroll

I thought id done a good job, my bits all neatly ‘tucked’ away, (being blessed with a small cock allowed me to push it back and have an almost convincing ‘camel toe’ in my skinny jeans) I was nicely made up, hoop earrings (not too large as to be too tarty) nice bra and panties, DD cup boobs, wearing my favourite brown modestly heeled over the knee boots, tight blue skinny jeans, cream cowl neck pullover and long black winter coat, faux fur scarf and mittens completing my ‘girl out for a walk’ look. Pretty good I thought, and I felt pretty good too. Done this loads of times, on my own, no probs…..until now………

Obviously the guy walking his dog I had passed earlier had read me…………………………….

I had passed him earlier, nearly an hour back, cute dog too, I smiled and carried on with my walk, enjoying the freedom of being out, dressed up and feeling nice and fem. I had stopped to take a picture with my new camera (one of my more useful Christmas pressies) and was looking in my bag for an empty sd card, when I noticed him turning back onto the same path as mine, odd as im sure he had done that earlier, now only about fifty yards away, looking straight at me…….shit…no other paths for me to take to avoid him.

I continued to look for the card, keeping an eye on him, hoping he’d just pass and carry on.

Nope.

‘have you lost something love?’ he asked,

I just smiled and shook my head, (sadly one thing I was not blessed with was a fem voice)

‘need any help?’

‘I’m fine’ I said quietly ‘thanks’

‘looks like you haven’t so much lost something but have something extra if you know what I mean’ he said, his eyes obviously looking me over, lingering on my crotch and chest.

I went to move away, thinking of the silly and dangerous position I had put myself in, but he gently touched my arm, ‘don’t panic honey, im not going to hurt you, although you are very convincing I know what you are’

Shit and double shit, On my own, can’t exactly run off (well not quick enough I suspected) and he’s read me.

‘I don’t want any trouble’ I said
‘no trouble, just wanted to chat and get to know you’
‘I’m fine, really, thanks anyway’ I said
‘I must say you look quite hot and I have a thing for trannies’

‘Trannies’ I huffed, almost indignantly, Great, I thought and the ‘thing he had for trannies’ appeared to be growing too…..judging by the bulge in his jeans.

‘Jess likes you too it seems’ he added, which was true as his dog was sat at my feet, looking up, looking cute. Ok, I thought, what harm …………….Although’ ffs Charlotte, just go. NOW !!!!’ is what my mind was actually saying)

‘Walk with us for a while’ he suggested
‘Ok, but don’t try anything’, ha, I almost sounded stern!

So, we walked, and talked, I relaxed and started to enjoy myself, we almost looked like a couple out for a winter afternoon walk! I told him about me (well some stuff I left out!), he told me about himself, Ashley, 42, a photographer (hence his ‘interest in me taking pics’), divorced, currently single
‘Own home, car, teeth and marbles too’ he joked.
Christ, now I feel like I’m on a date, but it could be worse I thought.

I had started to feel the cold, slipped my mittens back on and pulled my scarf a bit tighter
‘you feeling cold hun’ he asked, smiling.
‘a bit’ I replied, it was now gone four, I’d been walking with him for two hours!

He put his arm around my waist, but I flinched and he took it away, looking a bit put out.
I reached out for his hand and placed his arm back around my waist, my arm around him too, I gave him a smile and we carried on walking, I would have thought Jess would be about fit to drop, but she kept fetching sticks for us to throw, retrieve and repeat, way too much energy I thought.

‘looks like my stop’ I joked as we neared the path to where id parked earlier. ‘shame’ he said, then ‘can we do this again?’
I turned to look at him, and said ‘yes, that would be nice, but I don’t know when because of work and so on, but give me your number, oh silly, I have your card don’t I’ I giggled

(me giggling, like a teenage girl, jesus)

We had both stopped, and were now facing each other (what to do? I thought)

‘I will ring you soon’ I said, and pecked him on the cheek, then he turned and quickly kissed me on the lips, ‘naughty’ I said, but leaned forward and kissed him back, just a peck, then a bit more.
I moaned softly and pulled away, ‘next time’ I said, ‘I’m not a first date kind of girl’
We both giggled this time. ‘bye’ I said ‘call you soon’ and walked towards the car park, looked back and waved and headed off, feeling slightly lonely now, but aroused and excited?

To be continued


please feel free to comment constructively and any ideas or thoughts on where it should go next?