#1282 - Sissy Story 41 - Sarah's Story

Returns the appointment with sissy stories..
today with a really complete long tales about mature sissy..
In truth is a story of domination and first time experience with cock..
I wanted post this story expecially because i think there are a lot of virgin mature sissies..
for example like me.. with my 39 years old.. and older..
wanting to mean.. it's never too late.. for love..
life is always open for new experience also for us..
because everyone always deserves a second chanche!
enjoy the sissy story number 41! ;)
with love

Anna Malice




Sarah's Story




I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.
It had all started two weeks earlier when I had changed my profile on one of the sites that I regularly use. Up until then, I had been 'Mr versatile' – willing to do anything anyone wanted – pretty bland actually.
Now what I had written was the following:
"Young 52 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going whenever we meet. I am a submissive who loves the idea of doing as I am told and being humiliated as well. I have been told by other lovers that my oral is very good. However, I have barely had my bottom fucked in my life and would be looking for my top to change that. I also love outdoor sex. Anyone interested?"
For a week I didn't get anything. Then one day I got a reply:
"I would be VERY interested in meeting with you. Recently divorced and have own place. Wife walked out on me because of my bisexuality and left her belongings behind. Do you X dress as well? I am 63 and am still well up for it (as it were) and would love to use you. Particularly like the idea of taking your cherry, though I do love being sucked. Do you swallow? I'm afraid you will have to do as you are told and do so if we meet. I am into role play and would ensure that you followed my rules. Wonder, are you into threesomes/foursomes as well? I have some friends my age who would be interested. I live in Woking so would be willing to meet anywhere in the area and we could see if we are compatible. I include pictures so that you can see what you are getting yourself into. Let me know what you think."
WOW!!!!! I had never had a reply this explicit, this positive before. With shaking hands I clicked on the photos, three of them. One was of him full length and dressed. From what I could see he was about 6 feet and was a fuller build than me – ideal! He was reasonable looking and had a look about him of a man that knew what he wanted. The second was a picture of his cock. Oh god, I wanted it from the moment I saw it. It looked about 8" long, not too big, but long enough to choke me a bit and fill my aching bot. And it was fully erect! Lovely! The third was a picture of him full length naked. He looked good – a bit of fat around the waist, but haven't we all?
I'm afraid I babbled a bit in my reply – told him that I would love to meet him, would love to have his cock in me, yes I cross dressed when I had the chance and I LOVED 3 somes and 4 somes and I told him I was a virgin to this sort of game. I told him he sounded perfect.
I was also honest with him. I told him I was married and had to be discrete. I told him my time was limited when I could generally meet. To be honest, I thought this would lose him, but it's pointless being any less than honest. I ended with asking him if he could meet that Friday and if he could I would give him the best blow job he had ever had!
He must have been sitting at his computer, because I had a reply within 30 minutes. Yes he would love to meet me Friday at a time and place of my choosing where we could chat. He liked my age because young men were not as experienced. No he did not have a problem with me being married. He was self employed so his time was flexible. He lived in a flat in Chobham, so he was close to Guildford. He was particularly pleased that I cross dressed and liked 3 somes. He ended by saying he would keep me to the blow job, but I had to swallow.

I replied immediately – I was off Friday. Would 1.30 at the valley End car park be OK? I gave the type of car that I had and said that I loved this area because it was quiet and I could be naked for him if he wanted. I also included pictures of myself.
He came straight back that this would be fine and he told me he liked the look of me and that he would be there.
Well, I had never, ever had this positive a response before. I was sitting in my chair as hard as can be, my cock pushing through the material of my pants.
Friday 1pm came and I was out of the house and driving up to the Valley End car park. I particularly like this area because just across the road is some woodland where nobody but us closets go – not even dog walkers!
There are several good places, but my favourite is a small grassy enclosure where the sun shines and nobody would find you unless they knew it or were looking for it. This is where I planned to take him. So much for plans!
Earlier in the day I had gone to two separate chemists and bought KY in one and durex in another, just in case he wanted to finger fuck me or fully fuck me. I had washed my self as thoroughly as I could so I knew I was clean. I was wearing a pair of cargo shorts made of light fabric, a T shirt and sandals. And nothing else. I could be naked in less than ten seconds.
I thought about him cumming in my mouth and having to swallow. I had never swallowed any cum before, choosing to take it in my mouth and then spit it out. I'm not shy or squeamish about it, just liked to keep too much jizz clear of my digestive tract. No, the truth was I was waiting for a man who made me swallow – that I would have no choice about it, even within the confines of any role play. I would have to want to swallow and would have to submit myself to it. This is what gave me a raging hard on driving to the rendezvous.
But alongside that thought was the dream of his cock. Like most submissives, I dream of cock in my mouth. But it's not only that – it's the thought that someone will make me suck their cock – will taunt and tease me with it, making me beg for it, beg to have it in my willing mouth, beg for them to shoot their long streamers of cum over my face, in my mouth. And of course, having them push it into my mouth to the back of my mouth ad making me choke. I know the noise of choking will turn a dom on and that in turn spurs me on.
But it's more than that – the dom's cock is just the focus, the centrepiece for us subs. Yes for sure, it's the part of our dom's anatomy that we most revere and worship, but it's their attitude that makes the difference. The attitude that says "you don't matter – what matters is my satisfaction and my pleasure. Everything will be subjugated to that – do you understand slut?"
To which the answers are varied. "Yes Daddy" "Yes Sir" "Yes Uncle" "Yes Teacher". But they all only mean one thing – "I submit"
And what of my bottom? I had only been fucked about 5 times in all my 52 years, the most memorable being in a flat in Chobham where I had been used as a bitch, used being the operative word.
I so wanted someone who would gently introduce me to anal sex, maybe make me wear dildos up my tight ring until they thought I was ready. I shuddered inwardly as I though of finger fuck inspections of my little bottom, first one finger, then two, then maybe three, the size of the dildos growing as well and then finally his cock. Would he wear a durex? Or would he insist on bareback? And could I let him do that? I would have to wait and see.
The one other thing I thought about was his friends – all older, all doms and all wanting a bit of me. I had already cum dreaming about being bukakked by him and his friends. The times that I have been cum over have invariably left me cumming too. I love the feel of fresh cum running down my chin!
So all of this was whizzing round in my mind as I drove towards the car park and a meet that would change my sexual life.
As I drove up to the car park, my heart was pounding. Part of me thought he was having a laugh and would not be there. Part of me thought it was a set up. Part of me was scared that I would love being fucked too much and get 'slack'. Part of me wanted to give myself to him and let him use me. That was the part I was determined would win.
1.20pm I drove into the car park and I could see a green Mazda in there already. There were several other cars as well, the occupants of some I recognised (I would probably recognise their cocks as well as they had been down my throat at some time or another).
I pulled in next to him. He was parked in the middle of the car park and sitting at ease with his drivers door window open. I pulled up next to him. Close up, in real life, he looked even more fanciable and I felt my stomach lurch. I got out of the car and walked over to his window and looked down at him.
"Hi" he said "and who do I have the pleasure of talking to?" His voice was low, melodious and pleasant with an undercurrent of authority to it.
I cleared my throat and said "Chris"
"Hi Chris, I'm Harry – why don't you some and sit in my car?"
With a pounding heart I moved round to the passenger door and got in. he was wearing comfortable chinos and a plaid shirt and sandals. He looked totally relaxed.
"So you need a top?" he asked. I could only nod. "Nervous?" he asked "you don't know how much" I replied.
He smiled "I'm sure you won't be in a little while when you are more ahh...
occupied"
My stomach gave another flip as did my cock, which was rapidly growing to it's full 7 inches
He looked around at the car park. At the other cars. Back at me. "Quick test" he said "let's see how submissive you are – take off your top"
With shaking hands I took off my top and sat in the car looking round, because I was fairly sure what was coming next.
Sure enough "Now your shorts"
Nervous fingers undid the thin belt and I lifted my bottom up and shucked them off.
"And your sandals" he said, smiling. Off came my sandals as well
"You do realise you are sitting naked in the car of a total stranger don't you?" he asked "in the middle of the day too with other people in cars around us"
Weakly, I nodded. 'Say something' I told myself 'something that will impress my subservience on him'
"You told me too and that's good enough for me"
He did not reply, but undid his flies and put his hand in his trousers and brought out his beautiful cock I had seen only in a picture. It stood stiff and proud and looked bigger in the flesh. I licked my lips. I wanted it in my mouth. Now.
"You like?" he said. I nodded and did not take my eyes from his gorgeous weapon. He sat there gently wanking it. It was uncut, but he had pulled the foreskin back and I could see a bubble of pre cum appear in the slit. I could not stop my mouth.
"Excuse me, but I'd hate to waste that" I murmured pointing to the white froth on the end of his glans.
"Don't worry, you'll get some of that soon" he said, still smiling. "lean over towards me" he ordered. There it was, no change in his stance, but the authority was there in his voice.
I leaned over to him and he leaned down and placed his lips on mine and pushed. He kissed me so that everyone in the car park could see what he was doing. I let him lead and felt his tongue brush mine and around my teeth. I let go a little whimper. I was so turned on. Who wouldn't be, sitting naked in a strangers car, doing what he told me to, kissing him, whilst at least 4 other men looked on?
He pulled back "Now you can have it – but when you put my cock in your mouth, it won't come out until you have swallowed all my cum – do you understand?" The authority was back in his voice. I nodded and said simply "thank you"
His hand went to the back of my head and pushed it down onto his cock. As I came down towards it I could see he was not wearing pants and I could se he had big balls. Oh god! He may cum loads! I had visions of cum dripping out of the corners of my mouth onto his upholstery and him spanking me with others looking on.
My mouth was now down by his glans. I could smell it – it smelt clean and the drop of pre cum had formed into a sizeable globule. I had never wanted anything so much in my life, but I did not want to rush this. I wanted to impress my new top with my expertise.
Slowly, I opened my lips and let his glans sink into my mouth until all of the glans was in. I then let my tongue wash over his slit, lapping up all the pre cum. I then sucked on the glans gently, swirling my tongue around the head, bringing a groan from him.
He tapped my shoulder and said "it's alright, come up for air for a second"
Reluctantly I came up – I had only just started and wanted more. He pointed to the windows. There were three men from the cars watching us, two at his window and one at mine. I looked at him with concern on my face.
"It's Ok, you are among friends here – I just wanted to show you – now get down again"
Knowing I was being watched just made me randier and I turned to his cock with renewed determination. This time I took as much as possible into my mouth and sank myself around it. I almost got to the root and I sucked it gratefully. I was rewarded with another groan and heard one of the men say "the slut can suck alright"
I brought my head up to give him some more glans action, but he pushed it down again. He immediately pulled it up again and then pushed it down again. I got the message and started to stroke his cock with my mouth, up an down, so that it almost left my mouth and then went to stretching my throat. His hands did not leave my head though. He wanted control of the pace and I was blissfully happy.
"Relax" he said "let me push your slut mouth onto my cock"
I relaxed my neck muscles and let him use me like a cunt, fucking my mouth rhythmically up and down, up and down. My heart was beating fast and I could feel my cock waving about freed from my shorts.
"God you are good – I'm going to cum soon – remember what I said about swallowing" he muttered. He was now having trouble with his breathing.
His pace quickened as he pushed my mouth onto his turgid cock which was now rigid. I could tell the signs that he was going to cum soon and lathed the length with my tongue. Suddenly, he gave a grunt pushed my head down and his cock up. The net result was it was all in my mouth and forced at the opening of my throat.
I could feel his cock spasm and as it did, he pulled back so his cock was half way into my mouth. I sealed my mouth round his cock so I would not lose any jizz when it came.
Then he exploded in my mouth and almost filled it. God! I was right about his balls. I could feel his cum washing round my mouth and his cock still pumping more sperm into my willing mouth. And still he kept pumping! I had never had a man cum so much, only dreamed of it. The cum tasted fairly neutral and I had no problem with the taste. I pulled back a bit more and swallowed. For the first time I let a mouthful of cum slide down my throat. My cock was vibrating and I was very aware that I could cum without touching myself. I choked a bit, but was glad I had swallowed as another long stream of cum shot into my mouth. I swallowed this somewhat easier and he shot another load into my willing orifice. Would he never stop?
As the next stream pumped in he said "don't worry, I've been saving this for you for 2 days – and now it's all yours"
Two days? what would he be like after a week? At least he seemed to be slowing a bit now. I swallowed yet another lot (my fourth if I was counting right) and eagerly sucked on his cock. Now I had started, I wanted more!
After what seemed like an age, he slowed down and I came up and milked his cock with my hand, ensuring that I did not miss any cum. A small streamer pulsed out and I eagerly lapped it up. I looked up at him and he looked down smiling, approval on his face. His hand came down and pulled my face up to his and he gave me a long French kiss, his tongue swirling around my mouth. Then he pushed me back down and I willingly went back to work on his monster weapon.
This was the first time that I had fully swallowed a load of cum from anyone and I felt both so turned on and proud.
Eventually he pulled me off and I looked up at his flushed face.
"That was the best blow job – you were right, you are good. I'm not letting a mouth like that go"
I looked up and two of the blokes outside had their cocks out and were wanking, whilst watching us. One said "any chance of us using the mouth?" to Harry. I looked up at him, wondering what he would say. To be honest, I was cock and cum hungry now, like I'd never been before and I knew that I would suck them if he said so
"No" replied Harry "but he'll get out of the car and kneel while you three bukakke him, won't you Sarah?"
What could I say? He was right, my nerves had gone and before they came back I was out of the car and kneeling down at the back of it. One of the blokes repositioned me over to the back driver's side and I realised that Harry wanted to watch in his mirror.
All three gathered round and one said "I want to cum over his arse- bring him over to the fence"
They guided me over to the low fence which was only about 2' tall and pushed me over. The other two climbed over the fence and their cocks were at the same height as my face and the third I could feel rubbing his cock against my bum.
They were all masturbating furiously and I realised they were looking around because it was so public. I was worried too, but was totally overtaken by the moment now.
I whimpered "please, cover me in your cum, I want to feel it dripping down my face and between my bum hole. Please cum now. One of them leaned over and said "your top says when we all cum over you, you are allowed to cum, in fact you have to – got it?"
I nodded and put my face in line with his cock again. All three had 8" plus cocks, but the one behind me had massive balls as well.
Then the man on the left of me came over my face with a groan. Great long steamers splattered my face and I felt it run down my cheeks. He leaned forward and wiped it into my face with his glans.
This set the man off behind me and I felt what seemed like gallons run down my cheeks and onto my thighs. This was too much for the other man and he too came dripping all over my face.
As they all wiped up and used me as a towel to make sure they had unloaded all their cum, I put my hand between my legs and touched myself. It was enough. I came with a shattering orgasm.
I knew Harry was conditioning me to get excited about being covered in cum but I didn't care. I could feel it dripping down my legs and face and it was so good.
The three men all put their cocks away and got into their cars. I stood there strangely still turned on. Usually when I came, that was it, but this time I was still excited. Harry beckoned me to his window.
"In the boot there's a towel. Tidy yourself up and get in the car"I got the towel out and wiped all the cum off myself and got back into the passenger seat.
"Well you are a find aren't you?" He said "I never for one moment thought you would do any of that, but here I am sitting here with a big hard on again after that"
I was impressed if he was hard again after such a short time and the thought came into my head that he would want to fuck me now.
"I have KY and durex if you want to fuck me" I said, my voice low and vibrant. My cock too was rising again.
"Sarah, let's get one thing clear" he said "if I fuck you, it will be with KY but will NOT be with durex. Are we clear?"
"But that's not safe sex" I said
"Well, you can get out of the car and walk away now and not look back. I'll bet though that that orgasm you had just now was one of the best of your life"
He just looked at me. I looked him in the eyes. Then I lowered my eyes and knew he had won. Knew he always would. I knew I wanted more of this sort of wanton sex.
"Don't worry, I'll make others wear condoms" he said with a smile. But then it went. "But not me. I like to feel my cum pumping into my slut. Understand?"
"I understand Harry" I said subdued.
"OK" he said "and while we are making rules, you do not call me Harry. From now on you call me Daddy – understand?" The capital 'D' was important to me as it was to him
Oh wow. I was deep into sub territory now. Time to make a stand? Or was this what I really wanted?
"Yes Daddy" I said knowing it had nothing to do with fatherhood and everything to do with the submission of me to him.
"OK now get your clothes on and we'll go to Daddy's house. If you are really a virgin arse, we have to start breaking you in. And I see potential in you with dressing up. I think you will make a very pretty daughter"
As I followed him to Chobham, my stomach was churning. This had gone so fast. The most I had got myself into before was sucking two men off at once and ending up with two mouthfuls of cum. What I had just taken part in went way past that and more. But I found myself wanting more. I felt like a slut on heat and wanted to be used. I had never, in my 52 years experienced such a shattering orgasm. The recent taste of his cum in my mouth, the feel of the man's cum dribbling over my bottom, the streamers of cum dripping down my face, the feel of licking the small drips of cum from my top lip – they had all contributed to my cumming so hard.
But the main thing that had given me such exquisite pleasure was the fact that I had done it all after being told to do so by my Daddy. I had been naked in a public place, been used by 4 men and had not even thought of saying no. I still could not quite believe that I had done it and that alone meant that less than 15 minutes after my cum I was stiff again
I was feeling so turned on that I felt I would do anything for my new 'Daddy'. I mulled over this word in my head and again it felt nothing like fatherhood. It was a word to belittle me and humiliate me and I strained at the leash to be used like this. He had called me 'Sarah' – a girl's name and I loved it – more humiliation.
We stopped at a small block of flats on the outskirts of Chobham. Actually to call it a flat was a misnomer as he had the whole ground floor of a large house. I came to love this rambling shag palace, but on this day I was just aware that here was a man of means and he could afford to keep me in panties and KY
He unlocked the door and motioned me in. I went in front of him and stood by the wall, just inside. He closed the door and came straight to me pushing me against the wall and giving me another deliciously long kiss. I responded by pretending to push him away. My hands went to his shoulders (so big, so strong!) and tried to push him off. I whimpered deep in my throat and continued to push and felt him thrust back, pushing me against the wall, his mouth even more forceful. Obediently I stopped pushing back and gave in, eagerly allowing his body to crush mine, his lips to crush mine, his tongue to explore my mouth. I had thought this may turn him on more and by the feel of his cock against my lower stomach, hard and pressing, I was right.
He broke of the kiss and I gasped at the raw sexuality flowing between us. "I liked that bit of role play" he said somewhat raggedly (god, I was turning this man on!) "It had better be role play or you will get spanked for being a naughty girl Sarah. Now get your clothes off and go and sit in the living room". I dropped my clothes at the door and found my way into his living area.
It was tastefully furnished in modern blond wood furniture and large, comfortable sofas. There was a shag pile carpet in a contrasting deep brown on the floor and I felt it's velvety smoothness on my bare feet.
Bare feet! I was naked in a total strangers house, doing everything he said. My cock waved in front of me. I was afraid to touch it, lest I orgasm again. A fleeting thought passed through my mind that I should do that and get myself spanked, but no, that would not be a good way to start and I would have lots of spankings to come I was sure
I did not know where to sit, so I sat on the floor in front of a sofa that looked as though it was where he sat, my cock at attention, flapping in front of me.
He was gone about ten minutes, so I took time to study my surroundings. It was a very manly room with a large 42" LCD screen in the corner and an array of technical equipment underneath. I saw a several tripods and 3 video cameras and a high end digital still camera. I imagined that I would be videoed at some time and would be the subject of a show to his friends. I almost came at that thought.
He came into the living room, talking on a mobile phone.
"Yeah Jeff" he was saying "a right little slut and very obedient – let herself be bukakked by 3 others in the car park – yeah in public and no argument at all – I could not believe it at first either. And a very good mouth – haven't had one this good since little Pippa." He pointed at me and motioned for me to follow him. As I followed him, he continued to talk
"Yes, loads of potential. I've called her Sarah – yes I know that turns you on, me too" he laughed. "I'm just showing her the ex's clothes – I think that Sarah could fit very nicely – she's already shaping up to be a nice compliant little slut" He looked back at me and smiled and I smiled nervously back. "Yes, the usual – I'm Daddy and you'll all be her uncles. Yes I'm looking forward to the breaking in the daughter/niece role play as well"
He was talking about me! I was the slut he was talking about to his friend, the daughter/niece they would break in, the slut that turned them all on. I felt both humiliated and incredibly turned on by the conversation. His ex's clothes? Oh this was another fantasy for me. He was going to dress me up!
"Yes that's right, he needs breaking in – a job for Desmond the dildo and his friends I think" he laughed again. "But it will be nice to get my fingers up there and see just how tight she is in her boy cunt. Have to get an enema in her first though. Yes, see you later – yes I look forward to it as well. I'll be phoning Mike and Arnie later, bye"
Three others – all interested in using me. What had I let myself in for. And who was 'little Pippa'?
I followed him into a medium sized bedroom with a very large wardrobe in it covering most of one wall. All the doors were open and I could see the front of the doors had mirrors on them.
There was a double bed in the room with a large brass bedstead. I imagined myself tied to the bedhead at the mercy of my new Daddy and my Uncles. What was I getting myself into?
I looked in the wardrobe and saw rack after rack of woman's clothing. There were all sorts in there – evening dresses, skirts, tops. I could see several micro skirts. On one of the hangers, I saw a French maids outfit. There were several leather outfits and my imagination, already running wild, ran wilder.
I looked in the other wardrobes. There was a rack with about twenty pairs of shoes in there from thigh high boots to red stilettos. As soon as I saw them, I lusted after the stilettos. I longed to walk around the room in them. They had a strap across the instep and looked to be about 4" high.
I saw the drawers to the chest of drawers was open and there was all types of underwear in there from thongs to frilly French knickers.
And I realised that I would be wearing all of these.
On top of the wardrobe, were three wigs, one blonde, one black and one auburn, all different styles. Besides them was a professional make up kit.
He saw my eyes running over the make up.
"Don't worry" he said "I'll teach you how to put on the make up and then you'll be able to make yourself up when you come here for me and your Uncles"
I saw his eyes roaming over my body, could see the lust and the desire in them, the need to use. I shuddered and I think I may have whimpered a bit as well.
He sensed it and walked over to me, coming behind me. I felt his arms come around me and his hard cock pushing into my lower back. Gently he kissed the back of my neck and whispered in my ear.
"Don't worry my little Sarah, I'll look after you. All you have to do is be good. Later, I'll show you what happens if you misbehave, because you must be aware of the consequences. Somehow, I think you will like the punishments though"
I pushed back against him, enjoying the feel of his strong, manly body.
"Whatever you say Daddy, I'm yours to do with as you wish"
He turned me around and looked in my eyes. "I know my sweet little Sarah. Trust me, you will be used beyond your imagination"
Now my mind was working overtime
"What size shoe are you?" he asked
"Seven or seven and a half" I replied
"Good" he said "try these on"
He passed over a pair of stiletto shoes with about 2.5" heels. They were pink in colour and court shoes in style. I tried them on. They fit quite well.
"We'll start you on the low heels so you can practice walking in them and then you can go on to higher heels later. You have to get the walk right first. You have nice arse, but you will have to lose some weight."
"Now walk across the room and put some swing in your hips" he ordered
I did so, doing my best to swing my hips and making my pert bottom swing from side to side.
He made me walk back and forth in the shoes for about 10 minutes, looking at me from every angle. I did my best to keep up the sexy walk. I was so turned on again.
He made me stop and bend over
"Stay there like that" he ordered and left the room. He came back shortly with the professional digital camera
Here I was, naked except for a pair of pink stiletto shoes showing off my sexy walk to my new 'Daddy' with my cock leading me around.
He started to take pictures of me bent over
"I'll show you these pictures later and you will see where you will have to improve to please me. I can see straight away that you need a wax on your bottom and your pubes need trimming. Don't worry, family will not notice and I have ways of shaving body hair that does not attract attention."
I wondered how he would do that – I would love to be totally shaved and the thought of the clothes in the wardrobes was making me randier than I thought possible. This man was going to show me how to dress though, so I had to trust him.
"Don't worry" he said with a lustful look on his face. "I have a woman friend that will come around and show you how to make up and dress – in time, you'll be dressing yourself, but she will come round some time to join in. The only charge she makes is that she likes to fuck my little girls with a strap on."
He came round and took my chin in his hand. Pulled me towards him and kissed me long and deep. I felt my whole body vibrating as he made the kiss linger.
"But you'd like that my little slut, wouldn't you?"
"Daddy" I stuttered, "All this is like a dream. It's all I have fantasised about and more. You have shown me so much already. How could I say no to anything that you want me to do? And even if I did not want to do it, you would make me, which would only make it more humiliating and more sexy for me and for you. I'm standing here naked except for a pink pair of stilettos in front of you with you taking photos of me. You are telling me that a woman will be fucking me with a strap on. If my cock is touched now, I would cum again. Yes I would love it"
He put down the camera and came forward and kissed me again and my arms went around his neck as I returned his kiss. I could feel my naked body rubbing against his clothes and could feel his hard on pushing against me.
"Sarah " he said "I used to have a daughter called little Pippa, but she moved away with her work. She was a submissive slut like you and I will show you some of her videos because you need to learn what turns me on. Sometimes she visits because she misses me and she and you will have lesbian sex to please me and my friends. It would please me greatly to see you using your little girl cock to fuck little Pippa. Now another test. Come into the kitchen."
I followed him into the modern kitchen, stumbling a little in the stilettos, but nonetheless loving the feel of being naked except for a pair of women's shoes.
In the kitchen, he went to a cupboard and got a wineglass out and gave it to me.
"Sarah, you will find that from time to time, I will test your obedience to me and your Uncles. Failing to accept one of these tests may lead to punishments and even expulsion from our relationship. This is to ensure that you know your place as MY submissive slut. Do you accept this?"
This was a crunch time so early in our relationship. He was laying down a clear ground rule that meant I would have to do whatever he wished. Deep inside of me I made a decision. This would not be one off sex designed to give me a temporary thrill. This was long haul stuff. He wanted me to give all of myself to him. What I said surprised even myself.
"Daddy, I have learnt in the short time that I have known you that you are a very sexy man and have lots of sexual stamina. That alone would bond me to you. But you also have a lot of restraint and I admire that in a top. Already you have opened up places in me that I was not sure were there. This is more than short term sexual pleasure, I'm beginning to learn already what it is to be owned."
I took a deep breath
"When I fantasised what a situation like this would be, I imagined that there would be safe words and we could stop whenever I wanted, but I have a feeling you are looking for more than that. I want you to know Daddy, that I am willing to give you that level of commitment that you want."
Standing there naked, wearing only the pink high heels, I felt so turned on, so utterly controlled that I felt I would do anything this man asked.
"Sarah, I hope you mean that. Because if you do, you will experience sexual highs that you have never before. Sex becomes like a drug and I intend to make you an addict. Little Pippa was an addict and you will see on her videos what this meant. Now the test. You said that you may cum any second. Usually when a male cums, they lose their interest in sex until they gain a hard on again. I am going to condition you so that even when you have cum, you are still willing and available and turned on enough to satisfy your betters. You will cum into this wine glass. You will wait 3 minutes until the effects of the orgasm have worn off. Then you will drink your own cum. Do you understand what I want you to do?"
"Yes Daddy, I understand and I submit to it with pleasure. Not only do I get to have pleasure, but part of the process that means that I will give you and my Uncles pleasure has started"
"Good girl" he said "You are bright as well and I like that, although I can see that it will get you into trouble sometimes and you will have to be punished. Everything is subjugated to what I want and you will come to understand and love that. Now cum."
I put the glass down by my vibrating cock and touched my cock with my right hand. Already I could feel my orgasm coming on as I stroked my self gently. The thought that in 3 minutes time I would be drinking my own cum because Daddy wanted me conditioned did it. For the second time in 90 minutes (god was it only that?) I felt my cum shoot in streamers into the glass. I was aware of him watching me and all my senses seemed heightened. I could feel the edge of the glass against my glans, could feel the way that the stilettos fitted against my feet, the way that they stretched my calf muscles, feel the shudder through my body as my cum streamed into the glass.
Eventually it was over and I milked the last of the cum from my quivering cock. I put the glass on the worktop. There was about a quarter of an inch in the bottom of the wine glass
Daddy looked at his watch.
"Three minutes now. By this time you will have come down from your orgasm high and will not be feeling quite so randy. Neither will you feel quite so much like drinking your cum
As before in the car park, I still felt randier than normal. However, as time wore on and the minutes ticked by, my hormones calmed down. But beneath the post orgasm feelings there was another one: that in the short time that I had known this man, I wanted to please him and this overrode any distaste I had for drinking my own cum.
To my surprise, my cock was still semi stiff as the 3 minutes came to an end. I suppose I should not be surprised: my fantasies fitted so exactly with this man's that I felt that I would live in a constant state of turn on. Whatever it was, I was ready to drink my own cum to get more of what this man wanted to give me.
Nervously, I lifted the wine glass to my lips and tipped it up. I was determined that I would drink it down like a shot of Tequila and that would be it. Just as the cum started to flow down the glass, Daddy spoke.
"Don't drink it all at once my little sweety slut. Drink enough to get it in to your mouth and then show me." He hefted the camera into position to show that he intended to make a permanent record of my humiliation.
I slowly let the cum drip into my mouth. It was still warm and tasted slightly salty. I drank about half of it and brought the glass down. I swilled the cum around my mouth and opened it up to show it underneath my tongue and over my teeth.
Daddy (for I could not think of him as anything else) was obviously very excited and took several photos of my cum filled mouth. He fiddled with the settings on the camera.
"It's on video now – swallow for me there's a good girl"
I showed it again into the camera and then swallowed it down. Incredibly, I could feel my cock hardening again. Had he given me something? Or was it just that I was so excited that my fantasies had come true?
Again, I drank the rest of the cum and put my tongue in and licked out the excess, all being videoed. I swallowed it down and he smiled at me. Putting the camera down, he came up to me and gave me a large hug and kissed me again.
Pulling off the kiss, he said "It took me 3 months to train Little Pippa to do that and here you are after two hours slurping down your own cum. We really are going to have some depraved times with you."
With that he pushed me down onto my knees and virtually tore down his trousers and pants. He stuffed his rigid cock into my mouth and right to the back, making me choke a little. I put my hands against his knees and tried to push him away so that I could breathe, but he slapped them away, making it quite clear that this was not allowed. Chastened, I put my hands behind my back and left them there
"uuughhmmff" I whimpered into his pubes as his cock filled my mouth. Then he pulled it out and ruthlessly thrust it back in again. As soon as it was in, it spasmed in orgasm and the thick streamers of cum went straight down my throat, causing me to choke. This just caused him to fuck my mouth more and his hands held my head tightly against his groin as he shot more into my mouth.
Gradually the torrent slowed down and I was able to swallow the last of his cum. I looked up and could see the disapproval in his face as the last of his semen slipped down my throat
"That was naughty and you will be punished. Get in to the room by the living room on the right"
Intrigued and excited I went to the door and opened it. Inside I saw a small room about 10 feet square. The walls were plain and on the far wall, there were some rings just above my head height. I did not notice anything else because of the item in the middle of the room
The item in the middle of the room was a padded couch. The material of the couch was like you would find in a doctor's surgery – fake leatherette (easy to clean) It was about three and a half feet tall and about four feet long. It was about thirty inches wide. I could see that either end was hinged and had an arrangement that meant that they could be set at any angle. At one end there was a hole about six inches in diameter. At each end and down the sides were leather straps that came over the top. On the legs were other smaller straps
I could immediately see what it was for – for the recipient to be strapped on and fucked from either end. Their cock or their bottom would fit in the hole. They would be strapped down and tied to the legs of the couch. If they were not going to be fucked, I could see that they would be strapped down and punished.
My body quivered with the thought of being spanked on here. At that moment, Daddy walked in and he looked really stern.
"Ah, I see you have found the couch and I can see you realise the implications of it. This can be used for great pleasure or it can be used for punishment. Today, it will be used to punish you and also to start your path to being a compliant daughter. Lay down on the couch face down, with your little girl cock in the hole."
I lay down on the couch. It was cool and giving. I felt my cock go through the hole. It was not yet stiff again, but nonetheless I felt incredibly randy. It dropped down into the hole and hung down. I could feel how free it felt. Daddy came round and started to tie the straps. They each had buckles with lots of holes and he did my wrists first and then my ankles.
Then he lowered the back one so that my bottom was exposed. Then he did something I did not expect – he drew the bottom part of the couch apart where my ankles were so that my legs formed a 'Y' shape.
I lay there on my stomach with my girly dick hanging down, feeling the straps holding me to the couch. I still wore the pink stilettos and could feel their contours on my feet. I wondered what I looked like as my bottom half hung down lower than my top. Then I realised I may find out as Daddy took a tripod and video camera from a cupboard.
I had never felt so exposed and helpless – it was such a turn on for me even if I only had a semi hard on.
I saw in my peripheral vision Daddy setting up the video and then I saw him get a paddle out. It was about nine inches long by three wide and had a four inch handle. It was made of wood and he brought it round and showed it to me. I saw the spanking surface had what looked like a leather pad on it.
"This is what you will be spanked with Sarah. The leather pad means that you will suffer some pain, but it will not bruise you or leave permanent damage. As I spank you, you will count the spanks. To push me away from your mouth gets ten strokes. Sometimes I will make you wear a ball gag whilst I punish you. In that way we will build up a library of videos of you being punished"
He walked to the back and I heard the paddle coming down on my bottom.
Whack! It landed on my bottom and it really hurt – I was surprised at that and did not count one for the first spank
"No counting Sarah – that means 5 extra strokes"
"Sorry daddy – it won't happen again" I gasped
Next one – ooh that hurts – "Two" I said with gasp
And so it went on, the video camera remorselessly recording my humiliation and my counting each stroke
"That's better" my Daddy said "now we must start to prepare you. I will be back in a minute"
He left the room and shortly came back holding a small tube
"What is that Daddy?" I asked in a small voice
"It's lubricant for your tight little arse. Today I am not going to make you have an enema but every time from now on when you come her, the first thing you will do is to clean your colon and bowel. Louise will be here next time to show you how to do it – she enjoys that sort of thing and you will come to love her ministrations"
I watched as he put on a latex glove and covered the middle finger with the lubricant. He then moved to out of my sight and I felt his finger push between my cheeks. Trying to help, I tried to open my legs as far as they could go so my cheeks were fully open.
I felt the finger push at my anus. Felt it move around, pushing slowly into my tight little hole. Felt it penetrate me. Abuse me. Felt it push right up me until it touched my prostate. That came as a surprise as this gave me an immediate reaction – I became more erect than I felt I had ever been before!
He bent over and looked under the couch
"Hmm my little girl's girl cock has gone all stiff again. Say thank you Sarah"
"Thank you Daddy" I whimpered, pleased to be humiliated again and give him pleasure as his finger entered me again and explored my almost virgin anus.
"You weren't lying were you?" he said "you are very nice and tight. I will have to reconsider my use of dildo to break you in"
With that, he removed the finger and went to the cupboard. He got something out and turned around and I saw he had a replica penis in his hand. It was perfect in every detail and I could see that it was meant to represent a cut cock. It was about six inches long but quite thick – about as thick as mine.
"I can take that" I thought " It will be just like having me up inside of me"
He walked to my head and got the lube out again.
"Open your mouth now" I did so "I'm going to put a blob of lube on your tongue and then put the dildo in your mouth and I want you to coat it with the lube. Make a good job of it because it is going in your anus"
With that, he dropped a large spot of lube on my tongue. The couch was set up just right – my head was supported by a slight slope on the end, but my mouth was just off the end of the couch. He then put the dildo in my mouth. It tasted of rubber, but I did not let that put me off. He twisted the dildo in my mouth and I lathed it with my tongue until it was covered in the lube.
He withdrew it and examined it, but said nothing. Went to my anus end. I felt the cold rubber push between my cheeks, then stop, then come out.
"Back in a moment" he said
Shortly after, he came back in with another tripod and video camera and set it up at my mouth end. The he went to the cupboard again and got out a bright red ball gag
He must have seen my reaction – scared- because he spoke in soothing tomes
"Don't worry slut Sarah, because this will not hurt and you will have to get used to wearing it, come to like wearing it. Get an erection when it is put on you. So let me do it"
What choice did I have? here I was laying on a couch especially made for sex play, naked except for a pair of pink stilettos, strapped down on both wrists and ankles. All this and I had only been in his power for two and a quarter hours! I could see by the clock that it was only quarter past three!
He put the ball into my mouth. It was a soft plastic and fitted in well. Already I could feel myself beginning to dribble. He fastened it behind my head.
"Say to me 'I love you Daddy" he said
"Ough luf yur Dadder" was all that came out. I had never felt so helpless – he was now filming my degradation at both ends. Now not only had I lost the power of movement, but the power of speech as well. Safe words were of no use to me as we had not agreed one. And he had made it clear that he would not accept it anyway.
He moved to my bottom, apparently satisfied with the ball gag in my mouth. I felt the dildo push it's way in again between my cheeks and then onto my anus. He kept up the pressure and I felt it push into my anus, stretching it. It began to hurt and I squealed through the gag.
"Mmmmpphhh" I whimpered through the gag, but I guessed this just turned him on more and he pushed it further in. It was relentless and did not stop. It did not feel like six inches, it felt more like twelve and I wondered if he had swapped it for a larger one. It started to hurt less as it got in further and eventually I felt it bump against my prostate and stop.
"Good girl Sarah" he said " now I'm going to unstrap your legs and put tight pink lacy knickers on you and then I'm going to strap you up again. Don't worry, I know you have to be gone by a certain time, but we have hours yet"
he unstrapped my legs and I felt a tight pair of knickers being placed on my legs. I helped as much as I could, and they felt wonderful. One more step towards making me a girly.
I settled myself down to be as comfortable as possible. My body lay in a good position and my head was comfortable against the top end of the couch. Even the ball gag had settled down in my mouth and my breathing was relaxed. I knew that he would not let me be uncomfortable.
I could feel the dildo inside me and as I moved a little, it nudged my prostate, which sent tingles through my girly cock. He strapped me back up and went out again. When he came back he had a laptop on a little table on wheels. He placed it by the side of the table and turned my head so it was on its side. I was now resting looking at the laptop, which he proceeded to start up and then run a Media viewer programme. He paused the programme
"This is a 20 minute video of Little Pippa. It is her video and her wish to make it like this. It was made after her being in my care for about a year."
He put a button in my hand and I realised that it was a doorbell chime used in remote doorbells.
"I an going out and am going to leave you here to feel what your life will be like – subjugated completely to mine. If you panic or want to be released, the press the bell – I will not think any less of you. You have come a long way in a short time. Little Pippa took six months to reach this stage and she was a natural. Nod your head if you understand"
I nodded my head
"Nod if you agree to be left here. You can still watch the video in ter living room"
I nodded again. He clicked the mouse and left the room
I wondered how I had got here. I wriggled a little and felt the dildo move and felt the tingle in my girly cock again. Moved my mouth a little and settled the ball in my mouth. Stretched my arms and legs and felt the straps tight against my arms and legs. Settled down for Little Pippa's story.
A line came up "Little Pippa's Story"
I settled to watch