Ashleigh's First Kiss

After getting home Friday night I could taste John's cum in my mouth, I began playing with myself and dreaming of future encounters. If I had to wear a dress, am I OK with that? I began to imaging myself in a dress being taken by John, it made me so horny I came almost right away.

Over the past few weeks I have had numerous encounters with John, each time I would find a bag in my locker with something new to wear. After work I wait until all have left and then change into the new outfit, each time I get dressed I stand in front of the mirror and model for myself. Turning and twisting so that the dress or skirt moves as I move - it is very exciting and I find myself hoping to find a bag each time I go to work.

On this day I work a closing shift so I am hoping to find a gift in my locker when I arrive. As I am clocking in I check the schedule, but John isn't working so I am a little bummed. As I make my way to my work area my supervisor comes over and says "Harry wants to see you."

"Who is Harry?" I ask.

"He works in security, just go upstairs and you will see his office." she replies.

So I head to the back and up the stairs, Harry Jones was on one of the doors so I knocked.

"Come in" I hear through the door so I open it step in.

"Close the door Matt I need to talk to you" Harry says.

Harry has me sit down in one of the chairs in front of his desk and turns the monitor towards me, he indicates that he needs to show me something and ask me a few questions. I was OK with it so he proceeded.

He first shows me a video of two people leaving the building, a man and a woman. I recognized the people as it was me and John from Friday night.

"Do you know who this is?" he asks.

"Yes" I replied.

Then he shows me another video, it was of the back room and showed a man and woman with the woman on her knees with her head in the mans crotch..

"Do you know who this is?" he asks again.

"Yes" I replied.

"We have a problem because this violates several company rules, so I need to ask you about this incident."

Nervously I look at Harry, not sure what to say. "Do you know who this is?" I ask him.

"Yes" he replies.

Still not sure what to say or do I state "I did not know it would violate any rules, we were just having some fun." Then I nervously ask "What is going to happen to me, will you call the police?"

"Well" he says "we have a few options in this case. If you want to stay out of trouble I may need to have you do something for me."

"What would that be?"

"Are you sure you want to do this?" he asks "you may not like it."

"I think I will be OK, can I change my mind if I don't?"

"No, this is a one time offer" he says.

"OK, what is the offer?" I ask.

He says "Over in the corner are some clothing items, I want you to put them on for me and then we can continue."

I walk over to the corner and there is pretty pink dress along with a pair of pale pink panties and matching bra.

"Go ahead" he commanded.

I begin to undress, removing my clothes down to my underwear.

"Underwear too" he says.

So I pull down my underwear standing naked in the corner, I reach down and pick up the panties and step into them and pull them up, they feel different than the underwear I normally wear. They are tighter and feel better they smooth and silky feeling. I pull them up, they look like a bikini bottom and cover my cheeks and cock but my unshaven pubes are poking out the sides . Then I look at the bra, I have never worn a bra so I am not sure how to put it on. This one does not have big cups, they are small like with a training bra. I do the best I can and put my arms into the straps and then reach back and pull the band closed trying to catch the clasps. Eventually I managed to get the bra clasps to engage and I turn my attention to the dress.

The dress is not sleeveless but doesn't really have sleeves either, the sleves barely covers my shoulders. The neck is lower than any shirt I would wear and exposes my chest, the back also dips down and shows some of my back. The dress does not have a zipper and there is some stretch to the material so I pull it up and over my head, arms through the openings and I pull down on the skirt to get it all in position. The dress fits well and fairly tight to my upper body, the skirt is looser and pleated, hanging down to just above the knee. I feel myself in the dress, along my sides, to make sure it is fully pulled down. I then move around and make sure the skirt is pulled down over my ass and all the seams are straight.

All this time Harry is watching me from the chair behind his desk, "is this OK?" I ask as I turn to look at him.

"Yes, come over here so I can see you better" he commanded.

I walk towards the desk, arms to my side skirt swaying as I walk. He directs me behind the desk where he is. He pushes his char back and rotates it so that he is looking towards me.

"Turn around for me again" he asks.

I do as requested and turn around, slowly.

"You are cute" he says, "now turn around and bend over for me."

I comply and turn around to face away from him and bend over, he reaches over and squeezes my ass cheeks one at a time through the dress.

"You have a very lovely ass" he says.

I turn my head to look at him, "thank you."

"OK, now come over here and sit in my lap" he says.

I do as asked and stand up then slowly walk over and sit down in his lap. Wrapping one arm around his neck him I lower myself into his lap, snuggling as close to him as I can.

He begins to stroke my back with one hand and rub my thigh with the other.

"How old are you sweety?" he asks.

"Eighteen" I reply.

"So young" he says "are you a virgin?"

As I ponder his question he moves his hand up my thigh and reaches the edge of the panties, he then begins playing with my dick through the panties. I am so hard at this point and he begins to circle the head of my cock with his finger.

"You are very wet, you seem to be enjoying this" he says "Do you have a name?" he asks.

"You can call me Ashleigh" I reply "and I have only had oral sex."

"Here, give me a kiss" he says. So I lean down to kiss him, all I can think about is where this is going.

I had never kissed anyone before, let along a man. Harry is an older man, my guess is late 50s but I don't know for sure. He has grey hair, a full head too which is good, and stands about 6'. As our lips meet his tongue reaches to part my lips and enter them, I meet his tongue with mine and we let them play together. While we kiss he continues to play with my cock with one hand and rub my back with the other, I can feel his member getting erect beneath me and press into the back of my leg, so I try to gyrate my butt to stimulate him further.

With his lips pressed to mine, his tongue exploring my mouth, his hand caressing my dick I cannot hold back and begin to cum, my cock pulsing as it ejects its load. I let out a slight gasp as he plays with my cock and the cum as it filters through the fabric of the pink panties. My body twitches as the orgasm subsides, my body relaxes in his arms.

"Good girl" he whispers "did that feel good?"

"Yes" I reply with a whimper.

"Good" he says, "I want to make you happy."

He pulls my head closer and kisses me deeply, a deep passionate kiss. He then lifts his hand from my cock to my mouth and presses each cum covered fingers into my mouth and I lick them clean.

"Now get dressed and go back to work" he whispers, "I will expect you back up here after your shift."

He kisses me one last time and I get up from his lap, as I walk away he smacks my ass.

I walk across the office to the corner where my clothes are and begin to undress, removing the dress and bra and as I start to take down the panties he says "leave the panties on."

So I leave the cum soaked panties on and put my work clothes over them, minus my underwear. I leave the dress and bra in the corner and leave his office, not knowing what was to come after my shift. I spend the rest of my shift thinking about what he has planned for me.

Ashleigh Swift