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My name is Tom, and just over five years ago my father remarried. My mum had gone to buy some potatoes one August afternoon, when I was eight, and I guess after fifteen years Dad finally got tired of waiting for those damn spuds. I don’t remember much of my mother; only that her hair was brown, her smile was gentle, and that she always smelt of fresh laundry and flowers. Needless to say, we changed our laundry detergent shortly after she left.
I had been off doing my Master’s degree in Australia when Dad met Fiona, his future wife, at some sordid little diner somewhere in East London at 2 in the morning. What my father, of all people, was doing in East London at 2 in the morning is beyond me. I have heard the story of their meeting, how it was practically love at first sight, a thousand times over and so know better than to bore you with any more details. The point is, after just 37 days he proposed and I was going to have a step-mother.
I was unable to attend the wedding, much to my father’s dismay, as the date coincided with my final exams, but headed home after graduation.
When I first met Fiona I’ll admit I was a tad taken aback. Dad had said she was a little younger than him, but at only 34 she was still a complete knockout. Shiny blonde hair, a slim figure and a chest that looked to be as perky as those I’d seen on college girls, all made me rather jealous of my dad. I know some people might think it wrong that I was so blatantly objectifying my new step-mum in my mind, but, trust me, if she were your new step-mum, you’d have done the same.
During the first 3 weeks my interactions with Fiona had been minimal. She didn’t work but was always popping to the store or chairing some charity committee. You know, Mum stuff. However on the morning of a big interview I had lined up, that all changed.
I had just got out of the shower to find that my suitcase was gone. While I was in the midst of looking for it, there was a knock at my door and Fiona popped her head in.
“Tom dear, oh! I’m sorry.” she paused upon seeing me dressed only in a towel.
“Someone moved my bag!” I was embarrassed to be seen like this by her.
“That’s actually what I wanted to talk to you about,” she said, regaining her composure “I took it downstairs.”
“Why would you do that?!” I was annoyed by this point. I was cold, embarrassed, and just wanted to get dressed.
“I just thought your clothes could use a good wash. I didn’t realise you hadn’t taken out a set to wear today.”
“Well I hadn’t.” I huffed. “What am I meant to wear now then?”
“Alright, there’s no need to get your panties in a bunch young man. Come with me and we’ll get you some of your father’s clothes to wear for now.”
I can’t say my pride liked the insinuation that I wore panties, but I guess I had been a bit pissy with her. So I had to wear my dad’s clothes for a day? It’s hardly the end of the world.
I walked behind Fiona on the way to her and my dad’s room, and couldn’t help but admire the way her hips swayed from side to side and how her white dress clung to her perky bum (which no doubt looked even better due to the 5inch heels she was wearing today). When we got to the closet she spun around so fast that she must have caught me staring. If she did though, she didn’t show it.
“We’ll have to be quick about this, there’s somewhere I have to be.” she said in a firm manner.
“Oh, okay.” I tried to hide my disappointment, but she saw right through me.
“You didn’t think I got all dressed up for you, did you?” she quipped, arching an eyebrow.
I couldn’t think of anything to say so I just laughed it off and opened up the closet. What I saw next though took me completely off-guard.
“Holy shit.” I whispered at the sight before me.
In front of my eyes was something from the far reaches of my fantasies. Dresses of all colours and styles hung from the top while large pigeon holes held all manner of skirts, tops and shorts.
“That is my closet.” Fiona remarks, breaking me out of my trance.
“Oh, um, yes, uh, sorry.” I squeeze the words out while closing the closet. I want her.
“Unless you’d rather borrow some of my clothes?” she smirks “my panties are in a drawer over by the window.”. Oh, she is evil.
“N, No thanks.” I manage to say, though the lump in my throat is getting considerably bigger. I can already feel a tingling under my towel as blood begins to travel south.
“Really? I bet you’d look cute in lace. Or maybe a thong?” She winks before turning back around and opening dad’s closet.
It is much more what I would expect: a few suits, some jumpers, chinos, a couple pairs of jeans, and the odd t-shirt — all very black, grey, brown and blue. Though I’ll admit I wasn’t really concentrating on much other than the thought of Fiona’s lacy underwear at this point.
“So what do you need?” she breaks me out of yet another trance.
You Fiona, I need you. Her back is still towards me as she digs through my dad’s clothes. What I wouldn’t give to be able to pin her against the closet right now and have my way with her.
“What size waist are you?” she doesn’t even turn around.
“Rick is a 36, so you’ll need a belt as well. I’d say you were a medium for t-shirts. What about briefs? Small?” she looks over her shoulder, catching my eye, as she says that last bit. She has a sly smile spread over her face.
“I, um… I, um, actually wear boxers.” I can’t believe the effect this woman is having over me.
“Rick doesn’t have boxers. I threw them all out; they were all raggedy. Besides, I prefer briefs on a man — keeps his package nice and snug.” she winks again, grinning from ear to ear.
“So what will it be?” she continues “your dad’s briefs, or one of my thongs?”
I am putty in her hands.
“Well honey?” she says after a few seconds of silence between us “briefs or thong?”
She keeps a completely straight face, her voice not missing a beat. At this point the lump in my throat is so big I couldn’t reply her even if I wanted to. I can feel the sweat in my palms as my nerves take a hold of me.
And yet, I can feel my penis begin to rise to the occasion. It won’t be long now; there is no talking it down. Not now, not with Fiona standing only a foot or so away from me. Not with the thought of her lacy thongs crashing through my mind. It will only be a moment till I am forming a tent in this towel. It will only be a moment till Fiona sees.
She begins to giggle.
“I’m only teasing Tommy dear.” She steps towards me and gently caresses my cheek with her hand “you’re such a little cutie.”
And there it is. I am completely hard, with Fiona standing right in front of me. If she took but one step closer it would surely poke into her.
Looking into Fiona’s green eyes I notice her gaze drop towards my groin. When they flash back up to meet mine, she shows no sign of having noticed anything.
“Let’s get you those briefs shall we?” she says spinning around on her heals and digging into the closet.
She must have noticed, surely? She looked right at it!
I was in the midst of this trend of thought when Fiona brought me back to reality with her sweet tone once again.
“These were all that I could find.” She said, giggling slightly, while holding up a pair of briefs for me to see.
“They’re, um, uh…” with one big gulp I swallow the lump in my throat “a bit big.”
“Yes, well, your father is on the larger side.” Her gaze drops back to my groin for a moment “you seem to be quite small though.” her eyes twinkle with mischief as she flashes me a knowing smile.
“I, um, normally wear medium for boxers.”
“Right, well, briefs are normally a snugger fit. Why don’t you try them on anyway sweetie?”
Fiona throws me the briefs, and I head into the en-suite bathroom to try them on. As I began to slide them up my legs there is a knock at the door, and Fiona’s voice comes sounding through.
“Tom honey, make sure to come out so that I can check if they fit properly.”
What? I’m a grown man; I know how to try on clothes. The implication that I didn’t somewhat cheesed me off a little.
I knew instantly that they were too big. Not only was the waist a little loose, but the material at the front sagged way from my body as if there were no support for it at all.
“How does it fit sweetie?” I may be mistaken, but I swear I could detect some concern in her voice.
“It doesn’t. It’s too big.”
“Well come on out here and let me see silly.”
“But it doesn’t fit!” I shout back. Why can’t she just trust that I know how to wear clothes for Pete’s sake?
I realise almost instantly, though, that shouting was a mistake. Fiona raises her voice at me for the first since our meeting.
“Tom would you stop being such a little girl and get out here!”
I begrudgingly turn the bolt on the door and begin to step out. Fiona is facing the window away from me when she begins to speak.
“Now that wasn’t so hard, was…” she stops when she is fully facing me.
She burst into a fit of girlish giggles.
“Oh my.” She sighs covering her mouth and attempts to regain her composure. Her cheeks are burning rose.
“I told you they were too big.” I say, somewhat bitterly, as I try to cover my crotch with my hands.
When she finally stops giggling, a mischievous smile spreads across her face, and the twinkle returns to her eyes.
“I’m sorry for raising my voice at you earlier Tommy. It’s just that I thought that you were acting like a little girl.”
That wasn’t what I had expected to hear.
“Uh… yeah. I’m sorry for shouting too.” I reply, still a little embarrassed about my state of dress.
“No, don’t apologies. It makes perfect sense now.” She continues as she steps closer to me “You were behaving just as you should.” She is so close that I can feel the warmth radiating off her body. “Like a little girl.”
“W-What?” I said, the lump is returning to my throat.
She giggles softly before looking me right in the eye. Her gaze then drops to my crotch, and then returns to my eyes.
“You’re tiny, aren’t you?” she grins from ear to ear.
My palms begin to sweat.
“Just like a little girl?” she steps into me now, our bodies pressing against each other.
The feel of her soft breasts against my naked chest is too much, and my penis begins to stiffen once again.
She leans over and softly whispers into my ear, “And little girls wear panties.”
We are staring deep into each other eyes. Fiona is grinning from ear to ear.
“I want to see it.” she speaks softly, without breaking our gaze.
“W, what?” the lump in my throat is back to its speech-stopping fullest.
“Your penis. I want to see how small it is; I think you should take it out.” She slowly moves her hips forward so that they are pressing against mine.
I can feel my erection swelling against her body. The fabric of my father’s boxers is thin and must be doing little to conceal my arousal.
Fiona stifles a laugh.
“I can feel it against me Tommy dear. Just.” She places one hand on my chest and once again leans in to whisper in my ear, “I bet your little dick will look so cute in one of my thongs.”
I cannot quite understand the effect Fiona is having on me. My mind is awash in humiliation, but my swollen member is the hardest it’s ever been.
As our eyes meet again Fiona flashes me a knowing smile. With one hand still on my chest, she begins to slowly slide down my body.
Her hands finally come to a rest on either side of my hips, and her face is but a few inches from my swollen member.
Without saying a word she hooks her thumbs into the waistband of my boxers. This is the moment. Her gaze is firmly on my crotch. I can feel the sweat forming on my brow.
Six years previously
“Aww it’s so cute.” Skye says between stifled giggles.
I am lying on her bed, my hands tied to the bedposts, completely naked. This isn’t how I expected the night to go. I suppose you could say that Skye is my girlfriend, we have been going on dates for the last couple of months, but this is the first time she has even seen me naked.
When she began to bind me to the bed, saying that there was a surprise in store for me, I thought my boat had finally come in. A few minutes later and she is laughing girlishly at my naked form.
“From the lack of a real bulge in your trousers I knew it wasn’t going to be very big Tom, but I never imagined it would be so tiny!” she can hardly control her laughter.
“It’s not tiny!” I snap back.
“Tom, honey, dear, it’s minuscule.” She says as she holds up her thumb and index finger — the international symbol of a small penis.
“It gets bigger, really!”
“Uh-huh, sure it does.”
“Well.” She arches an eyebrow mischievously “how big does it get?”.
My throat suddenly goes dry. I can feel the moisture in my palms and my knees going weak.
“W, what do you mean?”
“I mean, how big does your teenie-tiny itty-bitty little dicklet get? In inches. Or maybe centimetres is more appropriate for you.” A devilish smile is spread over her face.
“I… I dunno.”
“You’ve never measured?”
I shake my head ‘no’.
I didn’t think it was possible, but I swear her grin grew even bigger.
“Hang on a second.” She says as she jumps off the bed and disappears into the other room.
I’m tied to her bed. Where would I go?
Fiona’s hand is over her mouth; her cheeks are burning crimson. My boxers are by my ankles, and my manhood is protruding away from my body and inches away from her face.
“You really are a little girl aren’t you, Tommy dear?”
I cannot bring myself to speak at this point. The mixed emotions of humiliation and arousal have all but rendered me speechless.
“This has to be the smallest penis I’ve ever seen.” Fiona says before reaching out a hand to grasp it.
My dick immediately twitches, which brings a laugh from Fiona.
“I bet you prematurely ejaculate as well don’t you honey?” she looks up and into my eyes before slowing starting to stroke the shaft of my cock. Not with her whole hand, mind you, just her thumb and two fingers.
I can already feel the pressure buildings as my balls begin to tighten.
“C’mon sweetie. I’ll make you a deal. If you last longer than five minutes…” she quickens her pace, and I am on the edge “…I’ll put it in my mouth.”
And with those words my body convulses and I erupt, strings of my cum landing on the carpet between us. One manages to hit Fiona right in the cheek.
“Is that it? I suppose I shouldn’t have expected much from something so small.”
She slowly brings her hand up to her faces to wipe off my goo, before rising to her feet and heading for the bathroom door behind me. I turn and watch her hips sway.
Just as I am about to reach down to pull up my boxers, she spins back around to face me.
She takes a step closer, and looks deep into my eyes.
Another step and the corners of her mouth turn up.
One final step and I feel her against my naked flesh.
She slowly brings her hand so that it is between both our faces, all the while holding my gaze.
Her other hand runs up my chest, along my neck, and cups my chin. It sensually applies a little pressure to bring it down, and leave my mouth open.
Before I can understand what it happening, I taste it. Fiona has stuck her fingers from the other hand into my mouth. The taste of my own semen fills my mouth, and my head begins to spin.
She pushes my chin back up as she begins to pull her fingers out, making sure I’ve cleaned them of all my juices.
She once again leans over and whispers seductively into my ear, “Swallow.”
“That’s a good girl,” Fiona coos, a mischievous grin spread across her face.
The taste is revolting and every instinct in my body is telling me I’m about to throw up, but Fiona’s gaze holds me steady.
“Well that certainly wasn’t five minutes,” she says, and giggles with one hand on her hip as she stares at my now rapidly deflating penis.
“Uh, yeah, um…” I am speechless.
“I cannot believe how small it is,” she says, as she bends down to more closely inspect it.
“Uh, um, yea, um…” well, fuck.
“And your father is so well endowed as well…” she lets her thoughts trail off.
“Um, uh, um, s-s-sorry,” I finally manage.
Fiona instantly pops back up and regards me with a wry smile. “For what?” She asks, playing innocent.
The lump is back in my throat, if it ever really left. “For.. Uh, you know,” I manage.
Fiona does her best exaggerated pout, “No, Tommy dearest, I don’t know. What exactly are you sorry for?”
“Is it for not doing the dishes last night?” She quips and makes a point of looking down at my now completely flaccid dick and smirks.
How did I end up here, I wonder?
“Is it…” she playfully shifts her weight from one foot to the other, all the while never moving her gaze from my crotch, “for not taking out the trash?”
“Oh wait, I’ve got it,” and her eyes flick up to meet mine. “Is it because you’ve got a tiny, little babydick, and prematurely ejaculate?”
I try to speak but words completely fail me.
“Well?” Her gaze is firm and unrelenting.
I can feel myself going weak at the knees, but also begin to sense a slight stirring in my groin.
Fiona takes a step toward me, “Well, honey, is that it?”
I try to look anywhere else but Fiona’s eyes have completely transfixed me.
She takes another step closer, so that we are now within touching distance. “Are you sorry because you have a pathetically small excuse for a cock that cums in less than a minute?”
My dick begins to come back to life, as Fiona’s approach continues. I step back but find myself up against the bathroom door. Fiona sensually slides herself forward so that our bodies are pressed against each other. Her white dress against my naked skin. She makes a point of gently, slowly and sensually, rubbing up against me.
She gives me a knowing smile. “Looks like you’re not sorry about that at all,” she says, making an exaggerating ‘tutting’ sound of disapproval. “You LIKE having a tiny, babydick that squirts too quick.” She smirks.
Her hand slides along my inner thigh before gently cupping my penis. She teases it with her fingers before giving it a few little tugs. She openly giggles. “I can jerk you off with just two fingers.”
I feel the pressure building once again.
“Admit it, Tommy.”
I tilt my head back in pleasure.
“Admit that you like me making fun of your cute little, baby penis.”
I’m almost there.
“Admit that your tiny dicklette is more like a clit, and that you’re just a sweet little girl.”
I’M ABOUT TO… and she stops.
My body pulses forward with anticipation. I feel the pressure right on the edge. Either she finishes me and grants me my orgasm, or I’ll simply dribble into her hand within seconds.
Fiona’s smile, as always, is a knowing one. “Admit it, babydick.”
And I do.
Six years previously
Skye comes skipping back into the room with a big grin on her face. She jumps onto the bed which makes me bounce and pulls on the ties that are holding my wrists to the bedposts. She places a ruler and her phone down between us.
“W-What is that for?” I ask, though I know precisely what her answer will be.
Skye giggles and arches her eyebrow at me. “Oh please! You really expect me to believe that you’ve never measured your tiny, little thing?”
“Uh…” I glance around the room in vain, trying to think of a way out of all of this.
“Yeah, that’s what I thought, little man. Now, do you want to tell me how big… Err sorry… I mean how SMALL it is, or am I going to find out myself?” She asks with a naughty twinkle in her eye as she waves the ruler in front of me.
I sigh in resignation to my fate. “Fine, I’ll tell you.”
“Ha! yes!” Skye claps her palms in excitement. “Okay one second…” she says, as she picks up her phone and points it toward me.
I ask, “W-What are you doing?” Though, once again, I already know the answer.
“Video recording your confession, obviously! God, the girls are going to love this! Now go on little man, tell the whole world just how pathetically tiny your excuse for penis is. Admit it, babydick.” she laughs and hits the record button.
to be continued…