I like my stories to feel a little more real than just an excited fantasy straight from a horny brain.
Its part fantasy, part fiction and part personal experience. This is part one and if people enjoy it there will be more to follow.
Feedback is appreciated, thankyou.
A Lady of Sqtature.
I had been living alone for about 6 months when i first met Steph.
I was out for a birthday meal with some family at a local restaurant.
Halfway through the evening i was a little drunk and in a good mood when i saw her.
Our table was near the stairs that led up to the bathrooms and i saw her walking towards the stairs. She was striking to look at, very tall, athletic frame and very strong looking legs. She looked like she was out with work mates, business type blouse, with a straight, tight, knee length skirt, shiny black stockings and heels. Her long dark hair framed her reasonably attractive face. Her perfect make up, dark eyes and red lips instantly got my attention. She was attractive without being gorgeous but the way she held herself, the way she moved, she just had an aura about her.
As she approached she glanced down towards me, just catching my eye as i quickly looked down realising i had been busted and she has caught me staring. Her stern gaze was enough to warn me. Beautiful big brown eyes but with a glare that sent a chill.
A little while later i looked up from the table and around the room. On the far side near the bar area a group stood talking loudly. As my eyes moved from one person to the next without really paying any attention, there she was… looking straight at me. An expressionless look, eyes fixed on me unblinking. I stared back for a few seconds, lost in thought before i realised it was her again. I quickly looked up, turned my head, looked down, any but at her, flustered. Slowly my eyes moved back to her, as i met her gaze again, she slowly turned her attention back to the man right by her in their small crowd. Was that a smile or smirk that just edged onto her mouth? I couldn't tell, i couldn't be sure. I watched her, looked at her, she was a few inches taller than the guy talking to her, and noticeably taller than the rest of her group. She really did stand out, in a good way. I was snapped out of my daydream by my cousin asking me a question.
The tall sexy woman was forgotten.
Another drink later, we were close to finishing our evening and i went to the toilet in preparation for leaving.
As i left the bathroom i heard a womans voice behind me "oh shit" and something thud on the floor. I turned around to see a purse rolling towards me and a woman bending down.
Without thinking i reached down and stopped the purse rolling and picked it up, moving to hand it back to….her!.
I held her purse out towards her and went to speak but no words came out. She gently took the purse, smiled "why thankyou, you are a helpful boy" she said with a slight giggle.
Still struggling to find words i was now more taken aback. "Boy" i must be 10 years older than her, i though.
Seeing my confused face and obviously struggling she sniggered.
"I do try my best" I finally managed and laughed.
"Thank You again" she said and held out a hand. Without even realising i took her hand and she shook it firmly.
"Steph" she said
"Erm Mike".
"Please to meet you erm Mike" she giggled again
"Me to" I blurted , unable to think clearly.
Her dark eyes had me fixed, transfixed, almost hypnotised. She wouldnt look away, just held me there.
"Do you always hang out around the ladies toilets trying to talk to women"? She asked with a glint in her perfect brown eyes.
I was staggered and lost for words "i , ah, i, i was just in the toilet" i stammered.
She laughed again "im joking, erm Mike, but can i have my hand back now please"? She asked with a big grin.
I looked down to see i still held her hand in mine. Going a little bit red i dropped her hand like it had burnt me.
"Erm sorry, er yes sorry" i looked down embarrassed.
"Thats ok, you have nice soft warm hands" she said.
I looked back at her, up at her, she was a good few inches taller than me.
She smiled again. "Well i was right, i knew you would be to shy to come over and say hi" she suddenly announced.
"What?" I said very confused frowning.
"Downstairs" she continued "you kept looking over, i guessed you fancied me the way you kept staring" she stated as if she was talking about the weather.
"I err"
"But i thought there's no way he will come and say hi, let alone have the balls to ask me out" she continued ignoring my look of embarrassment and wide eyes.
"So i followed you up here to say hi and ask you out instead" she said
I just stood there, mouth open, red faced unable to speak.
She put her hand in her purse and pulled out a business card.
"There you go, take that, text me tomorrow and let me know what night you're free for me to take you out" she said, pushing the card into my hand.
"Bye erm Mike" and with that she was past me and on the stairs as I turned round to watch her quickly but elegantly glide down the stairs.
I stood there for about 5 seconds just staring at my hand, at her card. My head swam with confusion and it wasn't just the beer.
I looked at the card in my hand.
Steph Rogers
HR Manager.
There was a mobile number on the other side.
I put it in my pocket and went back downstairs. I looked for her, but she and her group were gone.
It wasnt long after we finished up and i was home. All i could think about was this captivating Amazon looking woman. I cant text her now that would be to eager. I looked her up on social media and found nothing. An hour later i couldnt stand it any longer and messaged her.
"Hi Steph, its Mike. We chatted earlier, and you gave me your card and said to get in touch.".... send….gone.
I watched my phone eagerly willing a response… nothing. After 10 minutes i put my phone down disappointed.
I started to watch TV and in my half drunk state quickly fell asleep.
My buzzing phone woke me up, half asleep i opened the text message that had woken me.
"Well aren't we the eager beaver lol. Thats good though i don't like to be kept waiting.
Are you free tomorrow night?"
I had to read it again before i realised it was her!, she had replied. I was awake now!.
"Lol, i had better not keep you waiting then. Tomorrow is good yes, where would you like to go?".
I sent the message, excited and very eager for a reply.
Only a few minutes passed when she replied. "You had better not, or else.!. As for tomorrow i want to take you to a restaurant i like, i will pick you up at 7pm, text me your address… dont keep me waiting!!!". The smiley face after made me smile.
"Great see you at 7x".. i then sent my address, i waited but got no reply. I went to text again but stopped myself.
The next night i was showered and got ready for 6.30 and just waited, staring at my phone.
6.58pm.. "im right outside, quickly...don't keep me waiting
".I found I was quite nervous, and obviously excited. I grabbed a jacket and left the house. It felt a bit strange not getting into my car or driving on a date. She was parked right outside, a white range rover sport with tinted windows. I couldn't see in from the side and felt a little bit worried. Almost cautiously i approached and slowly opened the passenger door. There she was, looking gorgeous and smiling at me. "Get in, i don't bite" she said playfully.
I climbed in "hi, how are you"? I asked, being polite. "I'm very well Mike, thank-you, and you?".
"Good thankyou" i smiled back looking her over quickly and then looking around the car when she caught me looking "wow, lovely car" i blurted out.
"Thanks" she said slowly "and you look fantastic" i quickly added. She did as well. Black leather leggings with heels and a lovely woollen jumper that clung to her curvy statuesque figure. I felt captivated as I looked at her.
"Why thankyou Mike" she smiled.
" So Steph , where are we off tonight?" I asked.
"Tonight i am taking you to a lovely Vietnamese restaurant i like. Its lovely there and they do a few dishes that are to die for and you have to try them. You're no a vegetarian are you or have loads of food allergies" she asked almost sarcastically
I laughed "oh god no" i replied quickly.
"Thats good" she laughed.
She kept asking questions all the way there. I realised by the time we were parking I still knew very little about her, but she knew a lot about me, my family, that I worked in the offices at the local council etc.
She parked and began to open her door, as i reached for the door handle she said "oh sorry can you just reach into the back and grab my handbag please".
"Ok" i said and reached back, looking into the back seat i saw a black leather handbag and grabbed in. As I turned back my door opened and there she stood waiting for me. I climbed out, thanking her. She shut the door and turned away and walked toward the entrance a few meters away, missing me holding out her bag for her. Still carrying said bag I quickly caught her up in the entrance. She went straight up to the man at the podium just inside the door and spoke quickly. "Yes Madam, right this way please" he said leading her to a table in a quiet corner.
"Wow, this is lovely" i said as i sat down.
"Isn't it just" she exclaimed.
We chatted a little and laughed and a waiter came over for the drinks order. She looked at me and said "do you prefer red or white wine?"
"Ermm white" i said , a little surprised, i was going to order a beer but before I could say anything she ordered something i had never heard of. "Oh and i will order the food as well now" she said "certainly Madam" was his reply.
I was just about to reach for a menu and stopped and looked up.
She quickly ordered several dishes, again I had never heard of them or couldn't pronounce them. He scurried away and she looked at me and noticed my confused look. "Don't worry hun, i've ordered the dishes i spoke about, you have to try them, trust me" she said a little playfully.
I chuckled, shrugged and said "im all yours" then mocking our waiter's tone "Madam" and giggled.
She laughed and looked me straight in the eyes "hmmm i could get used to that name i think".
The waiter brought the wine to the table, he looked at me first and Steph quickly said "i will try that thankyou" before i even thought to speak.
"Of course Madam" the waiter said. She looked straight at me and we both giggled.
She tasted the wine and said " yes that's fine, leave the bottle" the waiter poured her some and she stopped him at about half a glass. "That's enough for me thankyou, I'm driving but my date here will have a large one please" she said without any emotion showing on her face, just a stare that said "Yes you will!".
We chatted and laughed as we ate our meals and I relaxed more as i drank more wine, which she kept topping up. It turned out to be a lovely evening and I felt we were getting on well. She called for the bill and the waiter went straight to her with it without looking at me.
"How much is it" I asked getting my wallet. "Please let me get this" i said.
She looked at me and said "oh no honey, you're my date and i'm taking you out, i brought you here, my treat". I began to protest and she held up a hand just as the waiter returned with the card machine.
She paid and left a £20 tip before getting up and leaving.
"Thank You so much" i said genuinely, before adding "Madam" and giggled, a little drunk. She laughed and as we walked outside i swayed a little.
"Oops, looks like my date's a little bit of a lightweight with their drink" she laughed. She stuck out an elbow "come my drunken little date, hold my arm" she laughed. Without really thinking i slipped my arm through hers and held it as she led the way. In her heels she was easily 3 or 4 inches taller than me.
As she drove back she turned down a road i didn't know and parked in a very small car park looking out over the town. "It's still early, i thought we could have a little chat before i take you home" she said.
"Ok, yeah" I half slurred and she giggled.
"I will be honest Mike, you're not really my usual type" she stated.
I felt my heart sink a little, i was honestly disappointed.
"Oh, erm.."
She went on, "you're quite a masculine looking guy, goatee, muscular and that. That's not my usual type, although you are smaller than me, i quite like that" she laughed. "But i have really enjoyed tonight and i quite like you and would like to see you again, if you wanted to" she said.
My eyes lit up, a little more uninhibited due to the wine i was a little to eager in my reply as i quickly blurted out " yes, yes of course i would love to see you again, i really enjoyed tonight and think you're gorgeous and really want to see you again, please…" she smiled and cut me off with a "shhhh" as she leaned over, held my face with one hand and turned it towards her and kissed me. A long slow sensual kiss, I of course responded. My eyes were still closed when she pulled away. I opened them all dizzy. She giggled.
"Lets have a little walk before it gets to dark" she said opening her door and getting out. I was a little slow getting my seat belt and as i turned and opened my door she was there and held my hand and helped me out. She kept hold of my hand and led me off down a little path by the woods. It was just starting to get dark. We walked, held hands and chatted a little for about 5 minutes and all the wine hadn't just gone to my head, i needed a wee and pretty badly. I giggled and said "i'm really sorry i need a wee" then stumbled a little. "Oh looks like someone's drunk let me help you dear" she said and guided me to the nearest tree. "Thanks" i laughed and waited for her to move away, but she didn't.
"Put your hands on the tree so you don't fall over again silly" she instructed and pushed one of my hands toward the tree. I half stumbled again and put the other hand out to catch myself. "Thats it just like that. Ahh ahh don't move" she said right into my ear as she stood behind me. Before i knew it her hands were round me and undoing my belt and jeans. I began to protest and moved a hand towards her. She pushed my hand back to the tree. "Stop being a silly girl and let me help" she scolded and yanked my jeans down quickly followed by my boxers. She took my cock in her fingers and held me tight around the waist with the other arm. She was very strong. She shook my cock "come on dont be shy" she giggled. "I'm not moving or letting go until you pee Michael so hurry up".
It took me a minute and i must admit was quite embarrassing but i managed it. She gave it a slow shake when i stopped peeing. "There there isn't that all better" she breathed into my ear. She kept her hand on my cock and continued to shake and then wank. My floppy cock soon started to stiffen. I started to talk and she shushed me and he free hand clamped onto my mouth and pulled my head back. Again i realised just how strong she was. "Now lets see what else needs to come out of this little cock shall we". My neck hurt if i moved plus her tight grip on my cock made it almost impossible to move. She held me in a vice like grip, hand over my mouth as she wanked me really fast. "Shhhh theres a good boy" she whispered "don't want any of the dog walkers round here seeing you getting wanked off now do we" she chuckled.
I was embarrassed, worried and turned on and was shooting my load in about a minute, just to add to my humiliation. "Mmmmmm" she groaned letting my cock slip from her grasp and giving my balls a gentle squeeze. I stood there a little confused and breathless as she slapped my bare arse and said "come on put it away. I better get you home" and laughed.
She dropped me back and kissed me goodnight and said she would call me and we can go out again.
The next day I couldn't help myself and messaged her. "Hi, thanks for last night. I had a great time. Sorry for being a lightweight but I don't drink much lol. Let me know when you're free again...Madam lol.xx".
I didn't get a reply that day and was kind of pissed off. That night I got disappointed thinking about it. She was lovely and had made a big impression on me and I had had such a great time. I thought everything had gone great but now i worried, was she not into me then and disappointed? Was this just the silent treatment to tell me to go away.? Just before midnight I messaged her again. "Hi i hope you're ok. I would love to see you again. Good night.xxx".
I waited 10 minutes hoping for a reply but got nothing. I fell asleep annoyed and sad.
The next day I really wanted to text her but couldn't, i would just look so desperate. So I stopped myself messaging her all day and went to bed disappointed. I was really hoping she would contact me the next day as she had said that she would call. By the afternoon I couldn't stop myself.
"Hi, is everything ok? I thought we had a good night and might be able to meet up again. I thought you felt the same.xx"
To my suprise 20 minutes later she replied. "Hi Mike, i did have a nice time but like i said you're not my usual type. I don't usually go for the rugged masculine type. I prefer slim, smooth, quiet guys. As you may have gathered i prefer things done my way. I do like you though you're a great guy and a laugh. And by the way i've noticed you've stopped calling me Madam!!! Lol xx".
I was so pleased to get a reply but bitterly disappointed it was the brush off. I didn't reply as I was annoyed with her and a little confused. But less than an hour later I just had to reply.
"Hello Madam
. I may not be your usual type but surely that doesn't necessarily mean i'm not the right guy for you???. I'm fairly slim (cough cough). Rugged? Well nothing a razor couldn't cure. I am a fairly quiet type (unless force fed wine all night by a forceful woman?). As you may also have noticed I am good at being led by a lady who enjoys things done her way and you will get no complaints from me on that….Madam. i think what you need is just a few more dates with me and to work your magic to have me more to your tatse.xxx". I waited for a few minutes and nothing. Shit! I thought. An hour later she replied. "Mike its all good and well saying these things but putting them into practice and sticking to them is another thing entirely. Im very serious when i say i prefer things my way, well what i mean is it has to be my way and thats it. I'm not sure you would like a woman making all the decisions. I am tempted to see you again but i don't think it would be worth it for either of us. I'm just trying to be honest Mike.xx".Again I was gutted to read her message but part of me also thought she hadn't completely said no. I really really wanted to see her again.
"Please Madam just give me another chance. I know you like me and I really like you. I would have no problem with you making all the choices, that's pretty much what happened last time and if i'm honest as well, i loved it lol. I'm even getting my razor out as we speak. Lets meet up again and see, I am quite happy to do as you say Madam if we can go out againxxx".
This time the reply was quick.
"Ok Mike i like the fact you are trying hard to please me. I will take you out again and give you another chance but it will mean you have to do as I say without question and we will see from there, agreed?xx".
"Yes Madam, of course, agreed. Just let me know when. Thankyou Madamxx".
I sent it and straight away and cringed, damn that sounded really weak and needy, shit!. She replied and I was a little worried about opening it.
"Good boy, that's what I like to hear. I will message you later. Can you make tomorrow night 6.30pm?".
"Yes Steph, 6.30 is great xxx" I replied.
She replied "???!!!
".What? Shit. I thought what have I done. I re read my last message and was. Confused?. Steph?? Ahhh shit! "Sorry, Madam". I put this time.
"That's better. Dont let it happen again. I will text later x".
Phew and wow she was quite bossy but i'm sure in a joking way and laughed.
That evening she messaged me.
"Tonight Mike, make sure you shave your rugged beard for tomorrow then lol. Also you should know i really dislike pubic hair!. Now this bit is important and a test to see if you can follow my instructions lol. When I pick you up at 6.30 I want you dressed only in, black socks, brown boots, blue jeans, and a plain black shirt.
I will be taking you for cocktails and a meal x".
"Yes Madam of course xxx".
That was it , no reply or anything. That night I shaved my goatee and my cock and balls. It felt weird, very nice but a little embarrassing as well..
The next evening I dressed as told and then thought what colour boxers? She hadn't said. I reread the message. It's a test! Boxers were not mentioned. I paused and giggled, commando it is then i guess.
6.30 she pulled up and I left immediately and got in.
"Good evening Mike" she said smiling.
"Evening Madam," I replied.
"So that's what you really look like"she said touching my smooth chin and giggled as she drove off.
I laughed. "You know i don't mind driving if you want a drink" i offered.
"That's very kind of you Mike but I won't be drinking tonight. Don't worry i will at some point in the future but when i decide"she added
"Of course Madam," I smiled. I was pleased it meant more dates hopefully and I thought it funny how it was a reminder she made the choices.
We got to a nice restaurant on the edge of town, very nice and quite busy. We sat in a lounge area on a sofa together and had a few cocktails before our table was ready.
She asked "what would you like to drink Mike?".
I had been reading the menu and remembered to be on my best impressive behaviour. "What would you suggest, Madam?" I asked quietly.
She smiled and ordered using an App on her phone. A few minutes later 2 drinks arrived via a barman. He placed a small straight glass in front of me with what looked like diet coke and ice and a rounded tall glass in front of Steph with a bright orange drink with a straw and an umbrella in it. She half scowled at him and swapped the glasses round. He just looked a little uncomfortable and left.
She smiled at me and said "I hope you like a slow comfortable screw Mike" and giggled, her eyes never leaving mine.
I Raised my eyebrows and said "I sure do, but I will drink this first" and we both laughed and she slapped my arm playfully.
2 screws later she turned to me and said "our table will be ready in 10 minutes. Now I need you to go to the bathroom first Mike but take my purse with you" she said putting her patent black purse in my lap. "Now what colour underwear are you wearing?" She asked.
I was really confused and looked at her purse then at her. "Erm what i erm i'm not er I'm not wearing any i…" I stammered and she cut me off.
"Very good Mike well done. Well inside my purse i've brought you some underwear as a gift and I want you to put them on for me in the bathroom and wear them for me tonight. Go on off you go and no peeping till you get to the toilet" she said pushing me up.
I must have looked so confused as i wandered off to the loo, feeling quite silly holding her purse. I went into a cubicle and opened her purse. It was empty except for a bright pink delicate silky thong. They looked very sexy then i realised she meant i had to put them on shit!. I wasn't too worried about wearing them. I was more worried why? Surely she wasn't going to shout it out or something. Then i remembered, this will be a test can i follow orders etc. She must think if he obeys and will wear these he will obey me on anything. I slid them on quickly and they felt amazing on my smooth balls and went back to her. She was watching me all the way back a sly smile on her face. I couldn't help but feel embarrassed and now quite self conscious, and thought everyone was watching me and probably guessed I was in womens underwear..
"Comfy?" She asked taking her purse back and giggled.
"Yes Madam" I said quietly, realising I had gone red.
"Oh you're too cute" she said "but a very good boy and i really like that Mike" she said turning my head and kissing me on the mouth.
We go through and eat our dinner. There's lots of small talk and getting to know each other and lots of laughing. I really like this woman and find her gorgeous, intelligent and hilarious. I also feel she likes me.
"I notice through your shirt that you have some chest hair Mike" she said.
I laugh a bit. "A little bit yes but i've never really had a very hairy body, luckily. I would hate to have had hairy shoulders and a back eugh" i say.
Her face goes serious and she says "never the less Mike i did say i hated pubic hair "
"Yes Madam of course and I shaved down there for you as well" I say a little sheepishly.
" well i class all body hair as pubic hair Mike, all of it except for whats on the top of your head" she said seriously "personally i've spent a small fortune and many hours having laser treatment all over so except for my head there isn't a single hair on my body. So surely being shaved smooth isn't a huge ask is it Mike?" she asked.
I got embarrassed and said "no Madam, sorry i will sort it for you".
"Yes you will, dear. Now how do your panties feel?" She asked, making me blush more.
I looked around quickly to see if anyone heard. "Erm ok" was all I could think to say.
"Ok? Are they comfy or too tight?". She pressed.
I thought for a second and couldn't even feel them "erm yes comfy, very" i said.
"Excellent" she clapped "they are so gorgeous as well aren't they?" She asked excitedly.
"Yes, very sexy Madam" I said smiling "they felt very nice on my smooth erm skin" i blurted out blushing again.
"Mmmmm yes they do. See how horrid body hair is now?". She said,
"Yes Madam," I agreed.
By the time we had finished and had more cocktails my head was fuzzy and I was drunk, again, and a little giggly. We were sat on a sofa again chatting.
"Mike i've had a fab night with you sweety i really have and you have been a very good boy" she giggled "so i think we will see each other again and if this continues, this fun together and your attitude remains like this i think i could get used to seeing a little bit more of you. If you would like that of course Mike'' she said.
"I would love that, yes" I couldn't say it quick enough "i've had another fantastic night with you and i really like you Steph, Madam" i quickly added.
She kissed me again, "Come on hot pants, let's get you home" she laughed.
This time there was no parking up or walks in the woods, much to my disappointment.
"Can i quickly use you loo before i go Mike?" She asked.
"Of course yes, erm come in" I said as I got out of the car. I unlocked the porch and then the front door and stepped inside. As soon as I did, I felt her grab my hair and pull my head back with one hand and push me in the middle of the back, sending me sprawling into the wall. My hands went up stopping me hitting my face which would be easy being this drunk.
"Keep your fucking hands on the wall hot pants" she ordered. With one hand holding my hair and head yanked back I could only see the ceiling. Her other hand had my jeans down in seconds. She reached into my panties and began wanking me. I was soon hard and she began wanking me fast into my panties. Again i could hardly move, i started to say something.. "shut it, not a word" she growled and wanked me faster. Embarrassingly again i cum very quickly, completely soaking my panties. She wiped her hand on my shirt and turned me round still holding my hair. As she was taller than me in her heels I was looking up at her, head held firmly back and my mouth open as I got my breath back. Her eyes were full of lust and she kissed me passionately. She let go of my hair and pushed me back into the wall.
"Night night sexy" she said and turned and left. I stood there unable to move for a few seconds then tried to go after her. Then realising I was in my porch, jeans down to my thighs and spunk covered pink panties on show, I darted back in and closed the front door.
I was annoyed, confused, horny??? And smiling. "Fuck me what a woman" i thought.
I got showered and into bed and sent her a text. "Thankyou for another wonderful night Madam. Maybe next time I can repay the favourxxx".
10 minutes later she replied.
"Well I doubt it very much sweetie. You know i'm always in charge so get used to it lol. As for repaying the favour, whatever do you mean lol?.
One, i always take you out, always! That is non negotiable. If its repaying the fun, well trust me i'm having far more fun than you lol. And if you're worried you are the only one being satisfied don't you worry, your time will come and when I need satisfying you will be doing just that
