So when I was younger, I got a lot of female attention from girls my age and older women, partly due to being above average attractiveness, having long hair, and being in a band. Having older women fawn over me may seem good to some and even to me now, but I wouldn’t say I liked it at the time. Older women were much more aggressive than girls my age, making me feel completely out of control. This reached its peak at a certain house party.

My friend’s parents were away, so he and his brother were throwing a house party. As his brother was much older and we were in University, they were a wide age range attending. I was having drinks and hoping to catch some girl’s attention. I was so used to girls approaching me that I still didn’t know how to be the first to make a move. But this night, there seemed to be only one woman interested in me.

She was an acquaintance of my friend’s brother from work. I had been warned by another partygoer that I had caught her attention, and as they knew, my M.O. had encouraged her to make the first move. When she was pointed out to me, I wasn’t disinterested. She was still younger than some of the older women who had been far too aggressive with me in the past, and she was very attractive. Short brown hair, glasses, and a slim body. I had heard later that she was self-conscious about having small breasts, but that didn’t bother me, as I like girls with small boobs.

While waiting for her to make contact, I did normal party things, drank, told bad jokes, and listened to music. As the night grew late, it seemed she wouldn’t make a move. Kind of a shame, but not the end of the world. Some people left to go home or to nightclubs, so the house was gradually emptier. While I was outside smoking, she finally walked over to ask for a cigarette.

“Thank you,” she said meekly. “I’m Chloe, by the way!”

I was familiar with this kind of approach from people my age. Still, the girl is making the first move, not being instantly touchy-feely and telling me I’m handsome like older women would. So I thought I was on to a winner. This would prove false as time went on.

I introduced myself, and we had a chat. We discussed the party, who we knew there, and what we were doing in life. She seemed very bright and kind. Her personality was drawing me in more and more.

“Are you sleeping here tonight?” she asked offhand.

That was indeed my plan. It was better than walking home drunk, and my friend had offered the settee.

“Yup, I have that as my bed,” I pointed through the glass French doors to the settee that was currently being used.

“Oh, that does not look pleasant!” she chuckles. “Tell you what, I walked from my house to here. It’s only about five minutes walk, you can have my spare bed, and I can drive you home in the morning!”

This seemed like a great deal. At worst, I got a comfy bed and a free ride home, and at best, I could lose my virginity to a sexy and brilliant woman. We walked to hers, still flirting and chatting as we went. When we arrived at hers, Chloe poured herself a red wine and grabbed me a beer.

“Count yourself lucky I rarely have beer here. But I only have two, so you’ll join me on the wine when you’ve drunk them.”

I enjoyed my time with this woman, and we went to her living room to talk more.

Her eyes are now deeply locked with mine. “So, what was your last girlfriend like?”

I blushed slightly. “I’ve never really had a girlfriend. I’ve kissed many girls, but it never went any further.”

Chloe let out a small gasp. “You’re not telling me you’re a virgin?”

I nodded in embarrassment. Part of me wanted to fake it until I made it, but lying felt wrong.

“Wow, usually, a guy like you at your age that’s a red flag,” she said cocking her head, curious for my response.

My anxiety was raising fast. “A red flag for what?”

“Oh, you know,” she raised her pinky and spoke in a high-pitched voice, “A little winky!”

Yeah, I was now uncomfortable. I let out a forced laugh. “I don’t know about that!”

Chloe slid closer and put her hand on my leg. “So you’ve had no complaints?”

“Well, not really, but then again, I haven’t shown anyone.”

I was now conflicted. I liked this girl physically and mentally, but her emerging confidence was starting to intimidate me.

“Well, this is the perfect environment for your first showing,” she barely finished speaking before her lips met mine.

I placed my hand on her hip as I kissed back, and she moved and glided her hand up my leg. I reflexively stopped her hand before it reached my groin.

She gently broke our kiss to ask me, “What are you afraid of?”

“I’m just really nervous,” I timidly smiled back.

“Well, would you like to stop, or would you like to lose your virginity?”

It seemed like an easy question to answer. “I would like to lose my virginity, please.”

I believe in always being polite and kind, but adding please to the end of that sentence felt humiliating and demeaning after I said it.

Chloe gave a sensual smile. “This is my first time taking someone’s virginity, but this anxious virgin vibe is turning me on!”

We returned to kissing, and her hand reached my zipper. Her finger unzipped my fly and worked its way into the opening. The kissing stopped once again. “Uh-oh, there’s the little fella,” her tone made me unsure what would happen next. “Honestly, what’s your opinion of your size, don’t give me that ‘I’m not sure nonsense’ because you must have watched porn or taken a sneaky peak at the urinal.”

My heart was racing. “I’m average, I think.”

This was more of hope than an answer.

She started audibly, “I think you know your wrong, don’t you, honey?”

The button on my jeans was undone, and she guided me out of underwear and jeans. I don’t know why I assisted her. I should have known sex was off the table, but sitting next to her, I was naked from the waist down.

Chloe began to fiddle with my dick as she spoke, “What we have here. Young man. Is not even a below-average penis. It’s an itty-bitty-baby-dickie.”

Her tone was still confusing, not mean, not sexy, just direct, like a teacher giving a lesson to a small child.

“What do you think of what I just said?” she asked.

I was stunned but wanted to stand my ground. “I disagree!”

She raised an eyebrow and nodded. “Oh, do you, now.” Her index finger and thumb gripped my shaft and started to stroke. She returns for a deep passionate kiss. Afterward, she looked me in the eyes to say, “If you admit it, we can keep going.”

I was now horny and desperate to continue. “I admit it.”

Chloe took her hand from my throbbing penis. “You admit what?”

I was longing for my dick to be played with. “I-I have a s-small c-cock.” I stuttered as I was so nervous.

An index finger was placed on the tip of my dick and began to circle. “No, no, no, calling it a cock is too generous. It’s not a cock. What is it?”

The contact was driving me crazy, and I began humping the air. “I have an itty-bitty-baby-dickie.”

I was rewarded with a sloppy kiss and her fingers on my shaft. “There you go! Doesn’t that feel much better? You should start your introductions that way from now on! ‘I’m Greg, and I have an itty-bitty-baby-dickie.’ The girls would love it, and you’d be honest with them.”

I was nodding along, enjoying the mini handjob I was getting.

“And you know what cements you as a little dick loser?” she asked.

I shook my head as I fucked her fingers.

She leaned into my ear, and her lips gently grazed as she whispered, “A real man wouldn’t have admitted that just to get his little micro pee-pee touched.”

My eyes widened in surprise, I felt as if I had been tricked into something, and now I was at the point of no return. My penis agreed. I let out a girlish moan to stop myself cumming, but it just made my orgasm more humiliating.

Chloe let out a delighted giggle. “Thar she blows,” she said, mimicking a pirate. “You’ve got a tiny baby dick, and you’re a quick shooter too? You should be wearing a sign so girls know.”

I was defeated and spent. I locked eyes with Chloe, not knowing what to do.

“Despite the lack of size, we were still going to fuck, you know. Now what am I going to do?”

I looked down at my shriveled dick dripping with jizz. “Im sorry.”

She sighed in a way that implied I should know better by now. “Sorry for what?”

I now knew the game she was playing. “Sorry, I came so fast.”

She didn’t even look at me. She was examing the jizz that was on her fingers. “And?” she asked with raised eyebrows.

“And for having a small—” Suddenly, a sharp glance from Chloe made me rethink my sentence. “For having an itty-bitty-baby-dickie.”

She smiled and shrugged. “It can’t be helped, but you can help with the cleanup.”

She absolutely could not be suggesting what I think she was. Her semen-dripping fingers were moving toward my lips. I started to move away.

“Do not be a wimp. It’s fine.” She dabbed her finger on her tongue and then swallowed. “See! And I might have been swallowing a lot more if you had not blown early. Also, if I were you, I’d be doing everything to keep me horny, and this will!”

What on earth was I thinking? Even now, I don’t eat my semen, but I was desperate to keep her happy. I opened wide and sucked her fingers clean.

“Well done, that was so sexy! Now it’s my turn to cum!”

Chloe took my hand and started to take me upstairs. ‘I’m still going to have sex with her,’ I thought.

“I never had a spare room, so this was always where we would end up.” She snapped her fingers and pointed to the bed. I sat obediently. “Top off too now,” she said as she got naked.

Her perfect body and tiny breasts made me horny, but it was too soon for me to be hard again. This did not go by without mentioning.

“A naked woman in front of you and your toddler dick isn’t hard? Last chance lost, my little friend!”

‘Please work,’ I begged silently and tugged my tiny dick.

“Hands off, or fingers off should say. I told you it’s my turn.”

She walked past me to her bedside table and pulled out a large vibrating dildo. Chloe caressed my cheek and smiled at me. “Don’t worry, honey. You get to watch!”

She bent over to scoop her panties from the floor and began talking to me like a mother would to her baby. “Now would you like to wear my panties while you watch me masturbate?”

I didn’t really, but I felt she wanted me to say yes, so I did. She clapped her hands in glee. “Such a good boy!” Once I was wearing them, she patted my groin gently. “Now, this is where itty-bitty-baby-dickies should go. And remember, this is as close to my pussy as that tiny micro tool will get now.”

She grabbed my hand and interlocked her fingers with mine as she lay on her bed and started to fuck herself with her plastic cock, and her breathing got more intense as she spoke to me. “You realize you did this to yourself? No forced you to admit your micro dick was useless, eat your cum and wear women’s underwear.”

She clutched my hand tighter as she built up her orgasm. “A real man would have stopped at any of them, but you said yes. I think you should start enjoying this more. It could become the only form of ‘sex’ in your life.”

I clutched her hand back, watching her masturbate, and her words made me horny.

“In panties holding your girlfriend’s hand while she gets pleasured by other means. Now I will cum soon, but I will cum to you thanking me. You’ll thank me for this journey I put you on, and you won’t dumb it down to save your dignity. It’s going to be the filthy truth. Understand?”

I nodded, both nervous and excited.

Chloe used my hand to guide me down to her vagina. “You’re going to say it to my pussy too.”

My face was now inches from her vagina, and my mouth was watering. She began to count down as her breathing became even more intense. “Five…Four…Three…Two…One….”

“Thank you for making me an itty-bitty-baby-dickie loser who craves to wear panties and watch girls get fucked with massive cocks!” I shouted.

Even I didn’t know I would say that before I said it, nor would it be at that volume. I was rewarded with a spray of juices from Chloe’s perfect pussy. Then, I don’t know if it was watching her cum, what she said, what I said, or the last trace of masculinity leaving my body, but I came so hard in Chloe’s panties that it dribbled right through.

Panting, Chloe patted me on the head, looking at my ‘shamegasm’ and breathlessly said, “Good lil’ beta, you are a fast learner.” She tapped the tip of my penis through the panties making me wince. “There you are. Although it’s a shame your going to miss out on my pussy scented panties due to your mini dicklette cum.”

She led me to bed, and I fell asleep spooning her ass. Chloe was teasing my little dick as we slept. At this point, I was so tired I didn’t even care. I was sleeping in jizz filled panties, and I’m sure Chloe wanted it that way.

The next morning Chloe drove me home with me still wearing her panties below my jeans. She dropped me off and said, ” I’ve got your number. We will do this again.”

Despite what she said and my now total willingness to do so, we never did anything like that together again. She would occasionally text me a naked selfie, a video of her and someone else in an intimate situation, or just a link to some very kinky cuckold porn. But we never met again, and she would eventually stop texting for whatever reason.

But she was right. I enjoyed it so much. It led me to so many other kinks and resulted in large masturbation addiction. Sissy porn, SPH, cuckolding, premature ejaculation, femdom—I wanked to it all and still do to this day.

 

The End.

 

*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.