The journey down on the train had been ok. My colleagues had chatted and gossiped most of the way whilst I read. We were attending a seminar on management (yawn), but that meant we were away from work for a couple of day and got to stay in a reasonably nice hotel. I was going to have a room to myself and was looking forward to some space from my colleagues, though they were nice to be around I was now feeling pretty horny and in need or release. And no wonder I was approaching my 27th birthday and two of my colleagues on the trip were in their twenties also: One, Sarah a blonde with medium sized breasts, shortish, wore geek glasses (that I like on a girl) and is nice and plump. Another Sandra, a red head, tall and slim with A or B cup sized boobs, glasses, and the most amazing legs (she was my work crush). The third was a lady I hadn’t worked with much before called Denise. She was of mixed heritage, Carribean and English, in her mid thirties, with big boobs and a nice curvy body and large butt. They had spent the journey either playing cards with me accross a table. Providing some nice images as they all wore clothes that showed plenty of cleavage. And when not playing cards they had gossiped amongst themselves whilst I read and covertly checked them out.
So we arrived at the station and shared a taxi to the hotel. The receptionist was a cute brunette with small boobs and a pretty face. My colleagues and I parted ways to find our separate rooms and quickly agreed to meet for a drink in a couple of hours. I was relieved to now have some time to myself. I walked up the stairs (I try to stay in shape and rarely use lifts) to the 3rd floor to find my room. Room 37, this was it. I opened the door and dropped my bag on the freshly laundered bed whose head rested on the same wall as the door, and scoped out the room. It was clean, white walls, bedding and nice cream carpet (that must have been a nightmare to keep clean). There was a small armchair in the corner, an en-suite shower room and toilet.
Exhaling and stretching I realise now is the time to take care of my built up tension. I open my black leather travel bag and find my laptop case containing the much needed headphones as well as the laptop. Logging in I discover that the hotel wifi is fast and ideal for my forthcoming activities. I start to surf around on my usual haunts until I find a great video of a red head woman being taken doggy style by a handsome white guy with the obligatary elephant trunk in between his legs. I move the laptop to one side on the bed, pull my trousers and boxers off. I stand to take my shirt and jumper off and decide to remove my socks too. It feels so good to be naked and i enjoy the sensation o the deep carpet on my soles and toes. I make sure my door is locked, lie back on the bed, apply my headphones and get down to business. Stroking my member with my thumb and two fingers, I quickly become erect and start to leak pre-cum. within a couple of minutes the red head is panting hard and making delightful female sounds of pleasure. I close my eyes and just listen to her satisfied moans as i continue to luxiourisly stroke my cock. My breathing deepens and I start to moan Sandra’s name as I imagine her and me in the places of the actors and the wonderful build-up of my orgasm approaches. I open my eyes to take in the sight of the red head being quite roughly taken now with both him and her clearly approaching climax. then I notice a small movement in my peripheral vision, I turn my head; cock in hand to find myself gaping at my colleague holding a phone clearly filming me. It’s Denise in a shirt and jeans, and she has a menacing grin on her face. As soon as I make eye contact she bursts out laughing whilst still maintaining the phone position on me. I freeze for a moment before covering my crotch with my hands whilst apologising and reaching with my left hand to stop the video with its orgasmic sound track playing. I’m apologising though I’m in my own room doing something private in what I thought was privacy (In double checking the door I must have unlocked it).
She sniggers and in her rich voice says:
“When I go to see a show, I like to watch it to the last act.”
I mumble and apologise again and then rally:
“Could you please leave and give me my privacy please.” I manage to say pretty firmly after clearing my throat.
“That would be a shame,” she croons with a grin of pearly white teeth, “I was enjoying myself and was willing to keep this newly produced film to myself.”
“What do you mean?” I quaver as my dick softens and shrinks under my hands
Responding in an almost sympathetic tone of voice “Well this is far too good material to keep to myself.” she steps closer to the bed.
“I wonder what Sarah and particularly Sandra,” her eyes light up on saying that name, “will make of the evidence that we have a small dicked colleague who they should forget about as a mate due to his inadequacy and obvious compulsive masturbation habits.”
She looks down at this point to my crotch and I burn red in the face and then look down at my hands in my lap.
“Now you know your position, I can get on with teaching you your place.”
My place? I wonder and swallow loudly
“Now to finish the show.” She exclaims and taps her thigh like a clap, as she continues to hold the phone to film me.
I realise I have little choice and hope that if I comply with her request then that might be the last of it and the humiliation will be contained. I remove my hands and the sight of my shrunken manhood causes a guffaw to escape Denise, and she moves to stand at the foot of the bed to get a new and better angle.
“Open your legs.” She commands softly
I open them and start to stroke my soft small cock, I’m nervous and am struggling to get an erection.
“Arrrr, do you have stage fright little one” and she wiggles her pinky finger at me in the universal small penis gesture and smiles a lovely wide smile, “Play the video again and think of sultry Sandra and your desire for her.”
I reach over, press play and continue pulling on my dick. The video and thought of Sandra definitely help my cause, but strangely the wiggle of the finger by Denise caused a confusing feeling of joint humiliation and arousal too.
I’m soon leaking pre-cum as I stroke myself with thumb and two fingers whilst my other hand massages my balls. I’m soon closing my eyes as I get lost in the moment and approach orgasm. I’m nearly there…
“Stop!” Denise commands sharply.
I immediately obey the strong female voice and even squeeze my cock tightly unconsciously to stop my self ejaculating.
“I have remembered that this isn’t just about the show anymore, and is about you learning your place.” Denise muses out loud.
“My place Miss?” I stutter
Miss where the hell did that come from?
“I see you’re already getting the hang of it.” raising an eyebrow and smiling again, ” Address me as Miss from now on.”
“Your place you see and probably know deep down is that of a beta male.” she explains
I blink and stare not knowing what to say as my dick softens again as pre-cum dribbles down to my thigh.
“You have a fit body but a small penis.” She calmly states with no malice.
She’s lowered the camera and is looking down on me imperiously but also almost nonchalantly.
“And you fantasise about being able to perform and please like a real, alpha male like in the video, but don’t act on your desires knowing that you couldn’t possibly,” She looks pointedly at my crotch at this point, “measure up.”
I hang my head in shame and start to cover up my pathetic shrunken boyhood.
“Ah, ah, ah.” she wags her index finger at me, “You now are to obey me and to ask my permission to cover up or go to the toilet, or do anything really.”
I nod and uncover my shriveled shame and a small tear even collects at the corner of my eye as my shame and humiliation become overwhelming.
“Oh honey, I know it’s a raw deal,” Denise coddles and walks and sits at the foot of the bed, “but you still have a place with women. Under them and pleasing them.”
I look up, into her eyes and see she is genuinely sorry for me. The pity softens me, but also adds to my humiliation.
“What future do I have with what I’ve got?” I plead with both voice and look.
“Well you see,” Denise look brightens and looks hopeful, “All women only truly want and deserve an alpha male who is fine specimen in every way.” She explains as she glances at my penis again.
“But Alpha males get cocky and full of pride in the knowledge of their superior position and they will not do all the things a woman needs to receive to be pleased.”
I raise my eyebrows in a questioning look.
“They rarely orally pleasure a woman and will not submit to her, which is the right of all women who are in truth superior to all men, even alpha males.”
I swallow hard and stare into her deep brown eyes in silence.
“So as you now know you’ll get to sexually interact with women, which must be better than the constant wanking you’re used to.” she juts out her lower lip and looks down at my flaccid member
I raise my eyebrows at this as I feel a glimmer of hope.
“It hadn’t escaped our notice that you haven’t had a girlfriend since working at the company and we had wondered if you were gay and in denial. Which would have been fine, but now I know the truth. You just know that you are completely inadequate material as a lover.”
Denise stands up on the bathroom side of the bed and I think I get a whiff of her arousal as she raises herself up.
“Now, go to the foot of the bed and get on your knees.” Her tone and look command me.
I stand up, remembering not to follow my natural instinct to cover myself up, walk to the end of the bed with my limp member bobbing side to side embarrassingly (that i notice brings a smile to Denise’s face), and kneel at the foot of the bed facing her.
“I’ll be back in a minute.” She grins mischievously.
I hear her use the toilet, which arouses me and a few moments later she re-enters the room wearing her shirt but nothing else. I can’t quite see her vagina from my position but the view is still spectacular. My penis starts to harden and raise itself up.
Denise looks down
“A salute from my new toy; how nice.”
She walks so she now stands over me and I can look up her shirt and gaze at her pink Labia and can smell her moistened sex. I unsurprisingly become fully erect.
“When was the last time you got to see a woman like this in real life?”
I swallow hard again.
“A few years.” I mutter.
“So what happened honey?” she asks the dreaded question
“Well… I erm had a girlfriend after a couple of years of being single and after a few months of my resisting to become intimate I gave in to her requests and we were going to have sex. I made sure the room was dark so she wouldn’t…”
“See your pathetic boyness?” Denise finishes for me.
“Yyyes, so she wouldn’t see me.” I continue
“Say that you kept the room dark to stop her seeing your pathetic, inadequate symbol of your masculinity.” Denise interrupts
I look up into her beautiful eyes and smiley face.
“I kept the room dark so Michelle wouldn’t see my pathetic, inadequate symbol of my masculinity.” I mumble in obedience
“Did the ruse work?” she asked clearly interested.
“No.” I look down again and catch sight of my now softening cock.
“I went down on her and got to glory in her beautiful body,” I swallow and my dick begins to harden again at the visual memory, “and I think I did a good job, but as soon as she felt my penis she cleared her throat, I think she stifled a laugh and told me she felt quite tired and would give me quick release and maybe we could do it in the morning. She gave me a quick hand job which made me spurt my cum over her fingers, which she wiped off on my shirt before rolling over and going to sleep.”
I look up again and see Denise smiling wickedly.
“She gave you a pity hand job?” She asked but not really as a question
“Yes Miss.” I reply and look down at her feet, which are beautiful and keep me erect
“Tom,” she wonders, “Are you a virgin?”
I look up into her eyes again, and see a look of incredulity on her face.
“No,” I answer quickly, “but I’ve only had sex once.”
“Not with Michelle by the sounds of it?” she asks
“No,” I look down at her feet again, “With my first girlfriend I had when I was 19.”
“She was 18 and had saved herself and we were both each others first.”
“Why did you only do it once?” Denise asks with a hint of mischievousness in her voice.
“Because,” I swallow in humiliation, “she said she couldn’t really feel it.”
This causes Denise to giggle and hold her hand over her mouth. She seems genuinely embarrassed for me.
“She was a virgin and still couldn’t feel your boyhood inside her?” she asks in a high pitched voice
I shake my head and look back down defeated. This whole time a weird thing is happening: I’m getting that confusing feeling of arousal and humiliation at the same time and my dick sports another small stream of pre-cum.
“And I guess you were wearing a condom?” she asks
I nod and look down at her feet again. She surprises me with the next question and I look back into her face quickly.
“Where did you find a condom that fitted your small penis?”
I blush and mumble
“On the internet, I had already tried… wanking with a normal sized one and could tell it was too baggy on me and I didn’t want an unwanted pregnancy so I found a site that sells different sizes.”
Denise lifts her had to her mouth again:
“You had to order especially small condoms to fit your tiny dick?” she bursts out laughing
“Can you imagine the look of the women there when they receive another request and the personal details of another shrimp dick thinking he might get lucky and in his desperation has to order small condoms?” She guffaws again.
My cock stays hard through all this, I’m turned on, oh god…
“How many girlfriends have you had?” she asks when she can collect herself.
“Three Miss.” I respond
“Is that because you have a tiny dick?” she teasingly asks
“Yes Miss.” I respond in defeat
“Did the others at least give you pity hand jobs?” she becomes interested again
“Yes Miss, and the 2nd one made me eat my cum of her hand.” why the hell did I tell her that!?
Denise is chuckling again.
“It seems you’ve already come across a woman who knew your place in relation to her. And all this talk of your humiliating sex history has got me all wet.” She says ending in a breathy voice as she lifts up her shirt, and it is clear by her moistened pussy that she is very turned on.
“Now you get to pleasure a female again.” She states as if it is a great treat, which honestly it is.
“Eat me beta dick.” she moans
She is standing and I have to raise myself up on my knees. I grab her curvy buttocks in my hands and start to delicately lick her labia and around her clitoris… which is engorged and is the biggest I’ve seen. It looks like a small penis its so big. I suck on it like I’m giving a blowjob and even bob my head up and down. Her nectar has a taste of iron and something I can’t describe, I love it.
“hmmm you’re a natural honey and you now have experienced my Clit which is almost as big as your pathetic penis.” she moans out.
I carry on orally servicing her and bring my tongue down to probe into her vaginal opening. Which hungrily swallows my tongue and gives me the sense that this is the biggest vagina I’ve come across. Before moving back slowly to suck on her clit.
Denise orgasms powerfully on my mouth and face whilst struggling to stay standing. She holds my face to her pussy and pants as she comes down from her orgasm.
She releases me and the air cools my pussy juice saturated face.