Getting into Her Pants

I first became my wife's occasional girlfriend as a result of her putting on a little weight. As long as I had known her, my wife had been a comfortable size 8. After she received a promotion at work she began getting a little stressed settling into her new job and her eating habits became terrible at the same time she began foregoing exercise. As a result, within the space of about six months none of her clothes fit her and she quickly moved from size 8 to size 10 and then to size 12.

At 5' 9'' and about 170 pounds I was reasonably fit, ate a balanced diet and worked out a few times a week. One time after showering I mistakenly grabbed a pair of her size 12 jeans and was somewhat surprised to see they fit me pretty well. As luck would have it, a few moments later my wife walked in on me while I was still wearing her jeans and I pointed out my discovery. The moment proved a key turning point for both of us.

She immediately broke down crying as she realized in an instant that she had gotten "so fat" that I could wear her pants. I of course moved to assure her that I still loved her and not to worry about it. Eventually she calmed down.

As we sat side by side on the bed, her still in her bathrobe and me wearing nothing but my briefs and her jeans she said, "Your butt looks pretty good in those, but if you want to wear them I should loan you a pair of my panties so they will fit better."

"To be honest, I like they way they fit. I like the way it's a little more snug at the crotch and in the butt. You're right though, they'd feel even better with different underwear."

Something about my comment sparked her passions and we began kissing and all too soon her jeans were on the floor and she was on top of me riding us to an orgasm. As we rested after our passions she said, "Starting today, I'm gonna start losing weight back to a size 8."

"I'll help however I can."

"I know you will. Will you do me a special favor?"

"Of course."

"I want you to put my jeans back on, with a pair of my panties. Something about you wearing my stuff really turns me on. If you keep them on all day, maybe we can get in another little workout tonight. That would be one way for me to take off a little weight."

Aroused by her passion and somewhat curious about my own feelings, I agreed to her request. That night our lovemaking was a little different and among the best ever. Normally our sex is pretty basic missionary position, sometimes with me on top and sometimes with her. That night however, she was very aggressive and was very vocal in her needs. She asked me to spend a lot of time kissing and caressing her breasts and she asked me to go down on her and spent a lot of time providing me instructions about how to please her there.

She told me how much she loved my tongue and lips and how she liked it when I took it so slow and gentle with her. She had expressed some of these thoughts before, but the way she did it was different this time. It was much more encouraging and she was much more responsive to my efforts.

I enjoyed the change of pace and was happy to spend the better part of an hour feasting on her body with soft kisses and caresses from top to bottom. I could tell my efforts were having an effect and eventually she took charge of the situation. She climbed up on top of me and started pounding herself down on me hard and fast. There was no question who was fucking who and she was clearly in control.

The way she was going I could tell she would cum quickly. Her eyes were closed and her breathing became ragged and then she started moaning and breathlessly saying, "Cum with me. Cum with me girlfriend. Cum with me...mmm you looked so good in those jeans girl. Mmmm you're making me feel so good tonight...."

At that moment I understood what this was all about it made me feel really good too. Seconds later she began to twitch and quiver and with a huge gasp she came as hard as I've ever seen her cum. Her climax set off my own and I spasmed hard several times deep inside of her.

Afterwards, once we'd enjoyed the quiet afterglow of good sex and were ready for a little pillow talk she confided that something about me wearing her clothes really struck a cord with her. She explained that as she thought about it during the day it was an odd mixture of wanting to feminize me and take the dominant role in sex combined with some vague lesbian fantasies that made the idea so alluring. She suggested that she didn't really know where she wanted to go with it, but really wanted to try it again.

I explained that I was surprised how much I enjoyed the feeling of wearing her panties. That the material was much softer and there was something kind of exciting about having a little secret on underneath my clothes. I suggested that it might be a little like when she wears her sexy lingerie out on a date. We giggled a bit about perhaps spending a bit more time at Victoria's Secret and then she asked me if I'd do it again, only maybe go a little farther next time. Maybe wear a bra or stockings for her when we made love.

I told her that I was willing to try it, but to give her some incentive I offered her a deal. I suggested that once she lost five pounds, I'd be willing to be her girlfriend for a night. I said I'd keep doing it for each subsequent five until she hit 20 pounds and then after that for each month she kept all 20 off. We negotiated a few more details and then she agreed to the challenge.

For my part, I was perfectly happy to help her fulfill a fantasy and would probably have done it without the little challenge. It was exciting to me to see her so charged up about having sex and I was very intrigued by her taking a more aggressive role. Equally, there was some part of me that was pretty aroused by the idea of being her "girlfriend" and I was curious to explore those feelings to see where it might lead.

Over the next month she worked diligently on her diet and exercise program and I supported her by doing the same. She easily lost her five pounds that month and I had nearly done so as well. A month to the day from when we started she had me spend the day in a pair of her size 12 black dress pants and panties. I noticed right away that these pants fit much different than the jeans that first weekend. Part of it was my own weight loss which made them fit perfectly at my waist line, but the rest of it was the silky lining inside the pants which seemed to caress my leg as I walked. I felt much more feminine in these pants. The way they hugged my waist and crotch seemed to give me a shorter, more graceful stride.

That evening after we came home from dinner, my wife added two items to my outfit, a pair of her trouser socks and a bra into which she had inserted some soft foam inserts. I wore one of my own turtlenecks over the bra and became immediately aroused by my new silhouette. Something about the clothing and the subtle gender shift had made me rock hard, which was noticed immediately by my wife.

"Liking your new look I see. Come over here girlfriend and let me see you up close."

"I do like it," I said as I walked over to her. "I like the way the bra hugs my chest. The fabrics of women's clothes are much more sensual. The lining of the pants, the silky smoothness of the trouser socks and the soft underwear all feel incredible against my skin."

Not much more was said that night since we were soon all over each other. We kissed, we caressed, we fondled and we sucked finally finishing with her on top encouraging her "girlfriend" to join her in a mammoth orgasm. When I awoke the next morning still wearing the bra, panties and trouser socks we were at it again for another quick round.

The rest, as they say, is history, and becoming "Stacy" one night a month has become a standard part of our sex life. After a few more months of dieting and exercise, my wife was back down to her normal size 8 and has maintained that level ever since. In fact, I think she looks better than ever since her increased confidence in the bedroom has encouraged her to be a little less conservative in her dress.

I also trimmed down a little bit and essentially inherited all of the size 10 and 12 clothes my wife had bought during her weight gain which I keep in a closet in a spare bedroom. As time has gone on I have added a few additional items of my own, particularly panties which I now prefer to wear almost everyday. Our dress-up has also progressed from a few slightly ill-fitting items to a full outfit, wig and make-up. Both my wife and I agree that I could probably pass in public, but so far we've kept our little variation to ourselves. My urge to give it a try gets greater each month and we've talked about some scenarios that would present few risks so maybe some time soon we'll have a girls night out.

Last weekend was pretty typical of our normal routine. Late Saturday afternoon, while we were enjoying a relaxing drink after the usual errand running and household chores of the day, my wife suggested that she was in the mood to get together with her friend Stacy and asked if I minded. I of course said "That sounds like a great idea." Immediately, the sexual tension of the evening had increased and we both knew that the night would end with some hot lovemaking. We spent a little while longer talking about our day and dinner before my wife departed to get ready. After getting a few things rolling for dinner, I did the same.

Becoming Stacy was getting easier all the time, but it still took me about an hour to get ready. I started with a shower during which I shaved my legs and made sure my chest was smooth and stubble free. I was never terribly hairy to begin with, but since Stacy had become a regular thing I began keeping my chest and legs smooth most of the time so it wouldn't be such a chore to get ready when the opportunity arose. When I was done I gave my face a good close shave and dried my hair.

In order to get into the right mood, I like to start by putting on Stacy's wig. Stacy's hair is shoulder length and strawberry blonde, a shade or so lighter than my own hair. The cut is conservative and reminds me of a young Martha Stewart. The minute the hair is on my head I immediately begin feeling more feminine and just as quickly my cock begins to rise. I ignore it for the time being and begin my make-up.

I start with a foundation that I apply all over my face, cheeks and neck. Over top of that I brush on loose face powder which gives my complexion a smooth even look. It took a long time and a lot of coaching from my wife to get this part right, but I'm now pretty comfortable with it and it doesn't take me nearly as long as it used to.

The eyes are still tricky for me. I carefully line my lids with a dark brown eye pencil. This takes forever since I'm so bad at it and usually mess up a couple of times. I add some light brown shading to give my eyes a subdued look and then use mascara to enhance my lashes. When I'm done with these I put on Stacy's glasses which have heavy dark frames in an attractive oval shape which make my eyes seem at once bigger and more innocent.

Next I work on my lips. My lips are fairly thin so rather than use a liner, which tends to make me look like a clown, I carefully fill my lips in with a medium red stick and then gently add a little gloss to make them stand out. I sit back and assess the whole and decide it looks pretty good. I very lightly add a little blush to my cheeks to give them a little hint of life, but on the whole I'm happy. I look like a 30-something business woman. Not a head turner by any means, but not homely either.

With my face in pretty good shape I move on to my outfit. Removing my robe I reach first for my bra which is satiny with lots of lace in a dusty rose color. Its my favorite and always makes me feel very feminine. I insert a couple of forms inside which together with the bra's own padding gives me a modest figure. Next I pull-up the matching panties which are a full cut with high leg openings. I love the way the satin panel feels against my hard unit and give myself a few gentle rubs. Eventually I'm going to need to get soft so I can tuck myself back between my legs, but for now I let it go.

Finally I pull on my sheer black stay-up stockings. As much as I dig the fantasy of garter belts and stockings, I'm really not comfortable in them and it's a little bit of a chore to get them on right. I like the stay-ups since they are sexy and make for easier access later, but I'm also perfectly happy with opaque or patterned pantyhose.

Next I pull on a black skirt and a pink semi-sheer cotton shirt. The skirt comes nearly to my knees as I stand and is a light wool blend typical of what a business woman might wear. The shirt is of similar quality. Its just sheer enough that someone might make out the dusty pink of my bra, but it doesn't look tarty. I button it up enough to cover my bra, but at the right angle I might show a hint of lace. I remember my wife wearing the exact same outfit to work one day, although she looked a lot cuter in it. Satisfied with my outfit, I add a gold necklace, a bracelet, a women's watch and a pair of conservative clip-on earings.

Shoes are always my favorite part of the outfit and I spend several minutes considering my choices. I consider my black high-heeled boots, a perky pair of lizard skin sling-backs and my adorable mary-janes with the three inch heel, but in the end decide to keep it simple with a pair of classic black pumps.

Checking my look in the mirror I see a fairly ordinary middle age woman dressed for an evening with a friend. If I added a jacket and buttoned a couple of buttons I could be off to a business meeting. I add a spritz of perfume and adjust my hair a tiny bit and then Stacy is ready to totter down the stairs and make her appearance.

My wife looked amazing. She wore a low-cut knee-length red halter style dress with black stockings and heels. Her shoulder length black hair was pulled back tight and her neck and wrists glittered with gold necklaces and bracelets. Her makeup was light and natural, except for her lips which looked full and wet in a shade of red that complimented her dress. Her heels were slightly over 3 inches and showed off her well toned legs to great effect. I'd learn later that the stockings were attached to garters which dangled from a black bustier. She looked fantastic and easily put her frumpy girlfriend to shame.

She greeted me with a warm hug and we gave each other gentle cheek kisses not wanting to mess up our make-up. After spending several minutes complementing each other on how great we looked and how nice it was to have a girls night together we quickly settled into our adopted roles. When we play like this my wife takes the part of the worldly girlfriend or older sister giving her more naïve counterpart tips on how to treat men, what it takes to be a sexy woman and fashion pointers. For my part I feed her ego telling her how she's so lucky to have such a loving husband, how sexy she always looks and how she's such a great girlfriend to me.

Bit by bit we make it through dinner and plenty of wine becoming more touchy-feely and more suggestive as the night goes along. Eventually my wife will lead Stacy by the hand up to the bedroom and the lovemaking will begin. When we make love as girlfriends its much different than our ordinary lovemaking. We might start by laying side by side on the bed fully clothed, my wife will reach over and gently touch Stacy's face bringing them together for a gentle kiss. A slow gentle kiss, a sip really.

Stacy will lie back submissively as my wife takes the lead and gradually intensifies the level and depth of the kissing. As they both get more and more into it, they will allow their hands to roam up and down each others bodies. Rubbing and caressing, involving the entire body in the slow build up of passion. They generally avoid the more erogenous zones focusing instead on back, thighs, fingers, necks. Special spots, known only to one another that give forth tiny bursts of woman to woman pleasure.

This will last for quite awhile perhaps well over an hour, nothing but lips and kisses, caresses and rubs. Eventually my wife will push the action ahead to the next level. She will push Stacy onto her back and suck her sensuously along her neck and across her shoulders, unbuttoning her blouse and removing it before moving her face back up to bite her lips and suck their mouths together. Taking the cue Stacy will unzip my wife's dress and gently slide it down off her shoulders.

The two will begin to grope and caress with more purpose now as they continue to make out in a much more heated fashion. Eventually Stacy will be left in nothing but her bra, panties and stockings and my wife will be completely naked. She will present her breasts to Stacy and demand that she pleasure them the way she likes. Stacy loves to worship her girlfriend's breasts and wastes no time burying her face in them. Gently she kisses each nipple to hardness. She'll use her tongue to bring each nub to perky hardness and then gently suck each globe deeply into her painted mouth. All the time caressing, rubbing, kissing, sucking applying pressure gently then firmly, never losing contact even for an instant.

Having mounted her, my wife will begin grinding her pelvis against Stacy's legs and pelvis while thrusting her breasts against Stacy's eager mouth and tongue. Stacy would run her fingers all around the nipple arousing the skin, and then would gently breathe on them and finally she'd kiss each nipple earnestly, with feeling, like a precious object. Pulling them back from her lips she'd breathe on them again, her hot breath sending a tingle of pleasure down my wife's spine. She'd then pinch them gently before kissing her breasts again and again all over as my wife moaned with pleasure.

Their eyes met and the lust flowed between them and once again they were kissing passionately my wife pinning Stacy's arms to the bed and pressing her head back into the pillow with the intensity of the kiss. Now it was Stacy's turn to moan. She loved to feel helpless. Their bodies both throbbed with desire.

Directing the action and wanting to build her arousal even more my wife rolled off of Stacy and directed her to use her tongue down lower. Stacy quickly complied, sliding herself on top of my wife and gently kissing and caressing her way down her torso. She will feel the softness of her body and smell the light flowery scent of her skin as she made her way to the center of my wife's arousal. Occasionally her hands or lips would brush a sensitive spot causing my wife's muscles to clench or encourage a slight moan. Their bodies were warming from the contact and their exertions. Gradually the room filled with the scent of their arousal.

At one point Stacy moved from her torso to my wife's hand, kissing her fingers. After a moment she sucked the middle finger deep into her mouth as though it was a tiny cock, wetting it all over with her tongue. Then she pulled the finger back out of her mouth and moved it up to caress my wife's pointed nipple, sending a shudder down her spine that was soon matched by Stacy's own.

Stacy then resumed kissing her way down lower and lower until finally arriving between my wife's legs. She buried her face deeply, inhaling her arousal before gently flicking her tongue across her engorged clitoris. This produced an instant shudder and my wife began trembling through her first small orgasm. Stacy continued her gentle ministrations licking the outer folds, dipping her tongue in deeply, brushing my wife's clit with her tongue. Stacy's whole face was buried deeply now, the bridge of her nose pressing against my wife's pelvis. Soon a couple of fingers joined in the efforts as Stacy sucked her aroused bud making her moan again as she built towards another climax.