Miracle Cure

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A young man discoveres a new cure for his sexual problems.
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I always had trouble with girls. Growing up I was a little bit introverted, which made socializing with people I didn't know a bit of a chore. But I never knew how to act around girls especially. Even when I was able to find the courage to talk to them, most of the time they just wanted to be friends. And the few times I actually went out on dates ended either with the girl going home bored, or worse, ending after a miserable attempt to go further.

I was a freshman in college before I saw a girl naked. She was a friend of a friend that was with me as a favor to someone else. And things with her actually went pretty well. Right up to the point where we decided to have sex. I thought all my troubles were finally over and I was actually going to lose my virginity. She took off her clothes and let me touch her everywhere. I was in heaven. But when it came time to complete the act, I was totally incapable of getting hard enough to penetrate her. And nothing she did had any effect. The night ended in humiliation and disappointment for me, and total frustration for her.

After that I pretty much gave up any hope of a relationship. Occasionally I would go out with a girl, and even get close to her. But the result was always the same. I would be raring to go until we were finally naked, then I couldn't get it up. Even the girls who were interested in me, and had the most patience, eventually gave up and moved on.

By my senior year I was living on my own in an apartment not far from school. Next door to me was a girl that was very of cute. Jill was slightly chubby. Not fat, just bigger. And that was actually a positive in my opinion. I'd been around skinny girls and they tended to be bony and stiff. Girls with a little bit of fluff tended to be soft, and often had bigger tits. She had wavy blonde hair that hung down to about her shoulder blades, big blue eyes, and full lips. She was about 5'4" with sexy, womanly hips, and as I mentioned, nice big tits. So I admit I had a bit of a crush on Jill.

Not that I had plans to do anything about it. I wasn't ready for another failure. But she was kind and we became friends. In fact, sometimes when neither of us were working, and she didn't have a date, we would hang out, (and I could add that she smells great to her list of attributes). It was on one of these occasions when she asked me why I never dated. Because she was so kind and gentle I finally opened up and told her my whole sad story. She listened to every word and never once laughed, or showed any kind of disdain or rejection. She seemed genuinely interested. I didn't think it would change anything, but it felt great to get it all out.

It was three weeks later that things changed. We had been hanging out a bit more often since my couch confessional. And in that time I admittedly noticed that she hadn't been going out on any dates. Not that I was complaining. I was very much enjoying our time together. On this particular night we were hanging out in her apartment watching tv and talking about school when she threw me a curve ball.

"Tim," she started, "I've been thinking a lot about your...problem. And I really want to help."

I was speechless. I really liked Jill, and had thought about being with her on more than one occasion. So the idea of doing anything with her caused me to pause. My mouth went dry and my heart sped up a bit. Then finally, "Uhm...what do you mean, Jill? What do you...uhh...have in mind?" As the words came out I felt like a total loser. It almost sounded like I wasn't interested.

Thankfully she picked up on what I was thinking anyway. "Well, I've really enjoyed being around you. You've actually become one of my best friends."

"But, wait a minute, Jill," I interrupted. "You have lots of friends. You go out, like, all the time."

She shrugged my comment off. "Sure, I have other friends. And I go out on dates. But nobody has ever really taken the time to get to know ME. All of my other friends are...basically pretty shallow. And to be really honest, once guys get to really know ME, once they figure out that I'm not all that they expected, they generally move on. You're really the only person that seems to want to be with me for who I am and not who you want me to be."

I listened to her words, both shocked at the revelation and touched by her sincerity. So I let her finish. "So...since we seem to be spending more time together, I thought I could at least...help you with your problems."

"You really don't have to do that, you know," I said. "I'm really ok with it. I mean, I guess I'm used to it and know that I'll probably always be...alone."

"But you shouldn't have to be," she replied. "You're a wonderful guy, and you shouldn't have to be alone." Then, after a few seconds of silence, she leaned in to me and kissed me softly on the lips. It was unexpected, but very nice. Her lips were soft and warm, and her scent was intoxicating. After letting her lips linger on mine for several wonderful seconds she said, "That is if you are interested in trying...with me."

I paused at her offer. I really wanted to, but I was afraid of another failure. Or worse, I was afraid it would ruin the relationship we already had. Again, she seemed to be reading my thoughts because she added, "Don't worry, Tim, whatever happens, it won't ruin our friendship. I just want to help you be happy."

She kissed me softly again before standing up and reaching her hand out to me. "Come on, let's go into my bedroom."

I hesitated for a moment before taking her hand and standing up with her. She pulled herself in close and put her hands together behind my neck. Looking up into my eyes she said, "don't worry baby. We'll go slow. And there are no expectations." Then she pulled me to her and we kissed again. This time I allowed myself to participate, and actually felt a stirring in my groin. I had felt that stirring before. I was hoping the end result would be different this time.

She led me into her bedroom by the hand, where we started kissing a little more heavily. After a long moment she pushed back a bit. Never breaking eye contact she hooked her fingers inside the waistband of her skirt and slowly pushed it to the floor. Then, grabbing the bottom of her blouse she lifted it up over her head and dropped to the floor beside her skirt.

She stood still in front of me, allowing me a look at her in just her panties and bra. She was every bit as lovely as I expected. Her bra was black lace and satin, and I could see her nipples and areola through the material. Her panties were black nylon with lace trim, and looked great as they highlighted her feminine curves. I found myself growing erect, and while I had been to this point before, something felt different this time. I was starting to wonder if I would actually lose my virginity at last.

Finally she stepped back in and we started kissing again. I let my hands wander over her nearly naked body, eliciting some soft moans and coos from her. Her skin was soft and smooth, and felt wonderful under my hands. I brought my hand to her front and cupped one of her full, soft breasts, running my thumb lightly over her hard nipple. My other hand explored her hip and gently cupped her ass.

After another wonderful moment I felt her hands tugging at my shirt. Our kiss broke long enough for her to lift my shirt over my head and then our lips came together again. Her hands went to my shorts and I felt them snaking down my legs.

We kissed in just our underwear for another moment before we moved onto the bed. We lay side by side, our hands roaming freely but slowly over each other's bodies. I reached behind her and unclasped her bra. Jill sat up and slipped the straps off her arms, allowing her ample tits to hang freely. I cupped the warm flesh in my hands and brought her nipples to my mouth. Jill moaned softly in appreciation.

Eventually her hand found it's way down to by crotch. As her hand pressed over my cock it felt as If I was almost fully erect. And as she slid her hand inside and wrapped her fingers around my member, my breath caught.

I continued to massage her breasts as she fondled my penis. "I think you're nearly there, baby." Jill said softly. "Let's get these off of you and see what we can do." She moved down and gently slipped my boxers off, leaving me naked on the bed. Moving back up beside me she took my semi-erect cock in her hands and started to stoke me. Her hands felt great against my flesh. But unfortunately there was very little response.

After a few minutes she looked down at me and said, "Let's try something else. I have an idea." She then rolled off the bed and stood at the side where she slipped off her panties. Again, she stood still for a moment, allowing me a look at her naked sex, her moist pussy topped by a neatly trimmed bush. I felt a stirring inside me again, but still my cock remained only half-erect.

Jill then did something I never expected. She moved back onto the bed, but down by my legs. The she took the panties she had just taken of herself and slipped them over my feet. I was in shock as she pulled them up my legs. Without thinking I raised my hips up enough to allow her to pull the panties all the way up.

The effect was almost instantaneous. The feeling of the silky nylon as it slid up my legs, then nestled against my cock, was mind-blowing. I had never worn panties, or even played with them. I really never had the opportunity. But laying there in Jill's panties I felt something inside me click like never before. And my semi-erect cock was suddenly throbbing hard inside them.

Jill looked at me with a satisfied grin and said, "I thought so. Hang tight, there are a couple more things I want to do." She then picked up the bra I had removed from her. "Sit up for a second." She added. I had no idea what she intended, or what was happening to me, but it felt so wonderful, and had me so hard, that I quietly obeyed. She slipped her bra over my arms and fastened the clasp in the back. I was surprised as how well it actually fit. But, therein again is another benefit of girls with a bit of substance to their bodies. The cups were obviously empty, but everything else fit pretty well.

She then got up off the bed and went to her dresser. She took out a nylon half-slip and came back to my side. "Lay still," she whispered. Then she took the half-slip and lightly dragged it over my body, from my toes up to my panty covered cock, then up to my chest and over the bra I wore. The silky nylon felt absolutely heavenly. And each time she brushed it over my cock I felt it twitch and throb against the panties.

After a few minutes of this heavenly torture she stopped and looked at me and said, "It's just what I was thinking. You have a very strong panty fetish. In fact, you're what most would call a 'panty sissy'. You are turned on by women's underwear to the point that you can't even get aroused without it."

I was stunned. "What are you talking about?" I argued. The thought of being a panty sissy was frightening, but also had a ring of truth to it. After all, she had just proved it.

In response she just put a finger to my lips. Then she moved over so that she was straddling me. She reached inside my panties and slipped my raging hardon out through the leg hole. Then, positioning herself over me she pressed my erection against the entrance to her pussy and lowered herself down.

For the first time in my life I was inside a woman. And it felt even better than I had ever expected. The only downside was that I was so excited, and so aroused, that I was cumming almost immediately. I grunted as I ejaculated inside her, felling a bit of shame at having lasted only seconds. But Jill looked at me sweetly and said, "Don't worry about it baby. We have all night. Besides, If my suspicions are correct, and so far they are, my little panty sissy will be just fine."

Being called a panty sissy again still felt a bit shameful. But as she started to move her hips, sliding her hot, wet, sex over my still rigid cock I was totally lost in her. She rode me for several long minutes before she started to moan and grunt. Her breathing was growing ragged and I could sense that she was close to an orgasm. And even though I had cum inside her already, my cock never softened. I had stayed hard the whole time and was actually nearing another orgasm myself.

Then just as I hit that point of no return and started spewing my cum inside her again, she arched her back and opened her mouth in a silent cry as her own orgasm overcame her. Finally she collapsed and lay beside me. We were silent for several minutes while our bodies came down from our orgasms.

Finally Jill looked up at me and said, "I think we found the cure for your problem." She kissed me deeply for a while, then she continued. "There's nothing wrong with you or your equipment. You're just not dressing right. So I think some changes are in order. But don't worry about a think. I'm going to teach you."

With that she got up and went to her dresser again. She took out a clean pair of panties and another bra that matched. She set them on the bed and then went to her closet where she removed a light summer dress. When she came back to the bed she commented apologetically, "I really wish you could stay all night and we could keep going, but I have an early class in the morning and I don't want to have to disturb you. So, in the meantime, put these on."

I climbed out of the bed and Jill helped me out of her black panties, which to my astonishment she put right back on herself. She also helped me out of her bra which she also put on, making sure I saw how she fastened the clasp in front and then turned it around before putting her arms in. Then I picked up the clean panties. I was trembling again as I pulled them on, still amazed at how great they felt against my skin. Jill helped me with the bra a bit, but it seemed pretty easy.

Finally she helped me slip the dress on. Again, I was astonished at how well it fit. Because I was 5 inches taller that her the dress was a bit short. But because of her wonderful dimensions it fit everywhere else. "There," she said. "That should do it. I think you're going to like this a lot better. What do you think?'

It took me a moment to find my words. Part of me wanted to protest. There's no way I was a crossdresser. But a bigger part of me was in awe and how great it felt. And it was that part of me that responded. "I think...you were right. I think I like it. It's a little weird. But if really feels pretty good. And that's even without...the other part."

She giggled as she snuggled against my chest. "You liked that, didn't you. Well, I thought it was pretty amazing too." She kissed me, and our tongues danced for several minutes before she pulled back. "Now, I have a confession to make to you." She paused for a second, then, "You commented earlier that I don't really have trouble getting dates. The problem is that...well...I have a fetish too. And when guys learn that...I want them to wear panties...it turns them off and the leave. I think that is what drew me to you. I sensed something different in you. And now that we've discovered...this...about you...I'm hoping we can have something that last longer than one night."

I agreed with her, in everything she said. And we kissed passionately again. Then finally she said, "You may be a panty sissy. But you're my panty sissy now, and I'm going to take good care of you."

As I walked across the landing to my own apartment I felt complete euphoria. Never in my wildest imaginations had I ever considered that I could be a panty sissy, or a crossdresser, or that it would feel this good. And all that on top of the fact that I had just lost my virginity to a very wonderful, beautiful girl.

I slept in the panties she had given me, and then wore them all day the next day. And all day long I couldn't escape to thoughts. The panties felt so wonderful that I just knew I would never again wear anything else. But I also kept coming back to Jill's last comment. What did she mean when she said she had big plans for me?

To be continued??

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AnonymousAnonymousabout 8 years ago
I love this story so much! PinkPennyPanties

Sugar,

As a life time crossdresser I have to say that. Your story is as close to reality how it is in real life. When my wife caught me wearing my own panties pantyhose with a bra and silicone breasts half slip and a pair of high heels. Which I bought myself because you should never wear any of your wife's clothes. They can tell if someone has been through their things.

I didn't know that my wife was coming home a day early visiting her mother. I was picking out a skirt and blouse to wear. I was downstairs were I hid my clothes. Picked out a blouse and skirt put them on then grabbed my makeup and wigs to use my wife's Vantiy.

Little did I know my wife watched as I put on my skirt and blouse. As I was climbing up the stairs I looked up and their was my wife. I panicked and ran downstairs to hide.

Long story short tells it like it really is. As in your story my wife and I talked things over. Great true to life story.

Thank you,

PinkPennyPanties

deanahiideanahiiabout 11 years ago
life

that is how life should be each of us finding that perfect person the sees who we are underneath and nourish that person.

AnonymousAnonymousabout 11 years ago
Loved it, Give us more

Oh, if only my wife would have done what the girl in this story did .....

Bambi_DoeBambi_Doeabout 11 years ago

When he said he could never get hard enough to fuck a girl I honestly thought he was a homosexual. But then she made him dress in panties so now I'm like cool he's a cross dressing homosexual. I know he just fucked Jill but I think he might be gay but its nothing wrong with that or the cross dressing. And no I don't think he's gay because he cross dresses but because women have never gotten him hard before.

MichelleDenimoreMichelleDenimoreabout 11 years ago
Hot

Very hot. Very romantic. I favour being dressed "en femme" for men however I found this story romantic Nd quite exquisite. I too wish I had some female guidance in the early days of my dressing to point me inthe right direction.

Michelle

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