Feminizing my Neighbor

Just the thought of it always turned me on, why I don't know, but it did. I was never able to live out this fantasy until David moved into the apartment across the hall from me. David was only 22 at the time and as soon I as I saw him; I began to fantasize about dressing him in my clothes. I am a single woman, 27, not drop dead gorgeous but damn good looking, with a body that stops guys in their tracks, especially my 38 D tits.

But I had never been able to convince any of the guys I dated to try on or wear my clothes and then I watched David move in. He just had this look about him, not rough and tough macho but soft features, a slender body, and very beautiful hair. I met him on the stairs as he moved in and that night, I had a mind-numbing orgasm just thinking about dressing him up. At that point, I knew I had to give it a try, somehow.

Over the period of the next month or so I invited David over to my apartment for dinner or just drinks and relaxing at least a dozen times. As he was new to the area and really didn't know anyone, he always accepted. I learned during this time that he came from a small town, was out on his own, and he even admitted that he really dated only 1 girl and that he found it difficult to be with women. In time he seemed to become very comfortable with me and I felt the time was right to give something a try.

And so, on a Friday night he was over, we were sitting together on my sofa, drinking wine when I said to him "you know David, I've noticed you wear basically the same kind of shirt all the time... a cotton shirt. Don't you find wearing the same kind of material, day after day boring?" I could see he was confused and so I said "take this blouse, it's a silk material. Feels wonderful against my skin and the color compliments my coloring. You really have similar skin and color to me; I just think you might like to wear something besides cotton."

I had taken his hand and had him feel the sleeves of the blouse I had on, and he said it really felt nice. I then said "I have another one just like this, is a peach color that I think would look really good on you. Come on, let's go put it on, OK?" and I had taken his hand, half pulling him up, off the sofa. He allowed me to lead him into my bedroom and as I went to the closet I said, "take that shirt off David." I removed the peach silk blouse and turned around to see he had removed his shirt.

David has no hair on his chest at all, so I smiled saying "I think you'll really like how this feels and looks." I held the blouse as he slipped his hands into the sleeves. I came around front and button the front up, stepped back and said "oh yes, I love how you look. Do you like how it feels?"

He turned slight red but said yes, it really felt nice, much nicer than his cotton shirt.

Over the course of the next few weeks when David was over, some nights I would have him wear one of my blouses, other nights I didn't. I didn't want to move too fast. Most of the blouses were very plain, a couple with a little lace on them but mostly plain. I decided to see if I could go a little farther with him, so I brought out a lavender satin blouse, with lavender lace trimmed neckline and lace trimming on the sleeves. In addition, the buttons were satin covered which made the blouse very feminine.

I said to him "I know this blouse is much more feminine than the ones you've been wearing but I know you'll really love how this one feel and I think you'll look really nice in it." He looked at the blouse and me and then proceeded to remove his shirt, allowing me to slip the blouse on him. I did the buttons for him and then turned him to the mirror. I was standing just close enough that he should have felt my very hard nipples on his back as I said softly "hmmm, very nice. I really like you in softer, prettier clothes."

It was a very successful night, and I was now thinking about how I could move on beyond just putting a blouse on him, when he gave me the perfect opening just a week later. I said to him when he came over "tonight I want you to go into my closet and pick out the blouse you'd like to wear this evening." He brought to me my ultra sheer ivory blouse, trimmed in very delicate lace. He was a little red as he handed it to me, saying this one.

I smiled saying "oh David, this is one of my favorites." He removed his shirt and right before I put it on him, I said, "a blouse like this is all about what you wear under it, it should be something special, something that makes you feel special." I then went over to my dresser drawer and brought back my all lace, pink demi-cup bra saying, "let's have you wear this, it's very special and will look really pretty under that blouse, OK?"

I held my breath as he didn't respond right away and finally said very softly "OK."

I smiled as I slipped the straps over his hands and then pulled the bra to his chest, doing the hooks in back. I turned him to the mirror as I adjusted the straps saying, "this will keep the straps from falling off your shoulders." I then held the blouse for him, and he placed his hands in the sleeves and kept him facing the mirror as I did the buttons up the front.

Again, I was close enough for him to feel my tits on his back, saying "very nice and very pretty. Tell me, do you like how the bra looks and feels?"

He very softly said "yes."

I said, "I'll be right back." I went into my closet, bringing out a very short, pleated skirt. I placed it in front of him, holding to his waist saying, "this skirt goes really well with the blouse you have on, I'd love it if you wore it too."

He hesitated for a minute and said OK.

I helped him undo his pants, letting them fall to the floor. He was wearing boxers, and his cock was fully erect, which thrilled me. I said, "you can't wear boxers under this skirt, but we'll fix that in a moment, let's get the skirt on you." He stepped into the skirt, allowing me to pull it up and doing the zipper in back.

I said, "reach up under your skirt and take off your boxers." Which he did while I went back to my dresser, removing the matching sheer pink lace panties. I brought them over to him and then held them as he stepped into them. I pulled the up his legs, under his skirt and over his very hard cock. We were facing the mirror still as I said softly in his ear "oh David, you look so sweet. Tell me do you like wearing my clothes."

At this point he seem to panic and started stuttering that it he shouldn't be dressed in girl clothes.

I cut him off saying "tell, be honest, don't you love the way the clothes look? Aren't you finding this incredibly exciting?"

He said yes but again, it wasn't right for a boy to wear girl clothes. I said to him "David, there's nothing wrong with you wearing my clothes if both you and I think there's nothing wrong with it. And I don't think there's a thing wrong with it, I love how you look, I loved dressing you in this outfit and I find it a huge turn on. And there's a real benefit for you."

I turned him towards me and unbuttoned the blouse I had on, removing it, leaving me in my black lace demi-cup bra. I took both his hands, placing them directly on my tits saying, "dressing you in my clothes is a fantasy come true for me, a fantasy that I find to be very exciting and because you let me dress you up and even better, you're excited wearing my clothes, we're about to have some incredible sex."

With his hands on my bra, I reached behind, undid the hooks of the bra and then held his hands to help him remove my bra. I placed his hands on my bare tits saying "I love having my tits played with a good long time. Just feel them, play with my nipples with your fingers, kiss them and even suck on them. There's no hurry David, I want you to really enjoy my tits." For someone so inexperienced sexually, he had a wonderful, sensitive touch and feel. He seemed to instinctively know when to pinch or suck a little harder on my nipples or when to be soft with them.

As he played with my tits, I directed his hands down to my skirt, helping him remove it and then took his hands and helped him push my panties down my legs. I was now nude, while he was still completely dressed in my clothes. I pulled his mouth off my nipple, took him by the hand and lay down on the bed saying "god, you're doing great with my tits, now do the same things with my pussy."

Maybe it was because I was so turned on by living out my fantasy, but he was really incredibly good with his mouth and tongue. As he took care of my pussy and tits, bringing me to a couple of mind-numbing orgasms, I was running my hands up under his skirt playing with his cock in the panties, as well as playing with his nipples thru the pink bra he had on. After having a particularly strong orgasm, I pulled away from him saying "god, I need to rest."

I had him lay on his back next to me so that I could unbutton the blouse, leaving it on him but exposing the bra completely. I removed his skirt but left him wearing the panties. I then started running my hands over the bra and panties, while saying softly "you have no idea how exciting this is for me." In a few moments he moaned he was going to cum, and I said, "it's ok sweetie, you can cum."

He then said, "but I'm going to cum in the panties."

I said softly "that's what I want sweetie, I want you to cream in your pretty panties." My hand was now right on top of his cock trapped inside the panties. I kept rubbing his cock through them and as I felt his cock began to throb, I cupped his balls saying "now, cum now sweetie. Cream those pretty panties for me. Do it."

He moaned really loud as his cock began cumming. I kept rubbing his cock and squeezing his balls saying "oh yes, baby, cum for me. Come in your pretty pink panties. That's a good boy." I had never seen a guy cum so much as he cock just kept on shooting over and over. When he finally stopped coming, he kind of collapsed, breathing hard.

When he recovered, he once again seemed very embarrassed but asked me if I wished he was a girl. I smiled, running my hands over his bra and cum filled panties saying "definitely not. It's the fact you're a boy wearing girl clothes that turns me on so much. I want you to spend the night and wear my pink baby doll nightie and panties." He let me put the very sheer pink baby doll nightie with the matching panties on him, while I slept nude.

We had many more dress up nights after this one.