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ladyboy44

sissy Why i am a cuck

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ladyboy44    23
ladyboy44

if you have just joined this story you can find the beginning under the same title in sissy cream pies, humiliation picture section.

However i will just to give a brief outline of the story so far. This all happened in 1981 to give you a sense of the period and peoples prejudices to those who were gay,bisexual or transvestites at that time.

When I married at the age of 21 I had very little experience with women as most of my past involved cross dressing and sex with men.

I soon found out being the so called man was not an easy path to follow as I had always been the passive partner and sexually satisfying women was a totally different and alien activity and to be honest a total disaster.

Not only having a 4 inch erect cock I also suffered from premature ejaculation. So I was incapable of providing a woman's orgasm with intercourse alone, that's in fact if I was to actually able to get as far as to attempt penetration. For the most part any heavy petting normally ended up with me cumming in my pants/knickers.

My wife soon became frustrated and started having affairs only a couple of months into the marriage. She did try to help me with more experience ( but not with her as she was totally fed up and had also found out about my cross dressing) and set me up with her friend, who was twice my age, hoping this would keep me satisfied and giving her total freedom.

Needless to say I soon humiliated myself on the date but learnt enough that the only way I could provide any level of satisfaction was through oral sex. However she also found out about my dressing and decided my only use for her was to become her weekend maid and oral provider.

I now knew I was under threat of exposure if I did not comply but during a chance meeting, I had fallen for one of her friends.

That is where my story has reached. So from this point I will continue from where I left off. As of yet I have left out names but this is probably a good time to introduce them.

Me: Paul

The wife: Sarah

The Mistress: Tracy

My lover : Lynne

So Without further ado, please enjoy my story.

When back at my place, Mistress wouldn't let up as to why I had an erection without any stimulation from her. Leading her to believe Lynne had something to do with it! Of course she was right but I was denying it saying it was because I was only thinking about servicing her.

" Strip" she demanded, As I did so she was saying "All girls have periods and that now includes you!" Taking out of her bag a sanitary towel and belt. " Now put this on and pull the belt up as far as it will go. That will cover and contain your sissy dicklet, but make sure you push that pathetic thing into your body! Ooh yes does Sarah use tampons?" Yes was my reply. "'Good go and get one and insert it into your arse, all I want to see is the string hanging out. Go on do it now! "

little did she know was that I had been regularly using both towels and tampons since I was 12. So if she thought it would be a humiliation for me, she was wrong. However I was still happy to be "forced" to wear them.

 

Anyway finding the pack of tampons I was pleased they were for heavy periods " bigger the better" in my case , removing it from the wrapper, lightly coating the tube with lube and then inserting as deep as I could then pushing the inner tube until fully inserted. Removing the tubes and pulling the string down, job done! I would normally use them after being fucked and to contain the seed within for as long as possible and to prevent leakage.

Both towel and tampon in place I went back downstairs to face what ever the bitch had in mind. " bend over I want to check you put that tampon in properly" she said as I bent over and she parted my bum cheeks and gave the string a little tug. " Well done sissy, I thought you would have had more trouble than that? Not easy inserting one for the first time. Any way tomorrow I want you to go into boots and buy 2 packets of Dr Whites and tampons one for regular periods and the others for heavy and I want see the receipt dated and time stamped. You must only use the ones for heavy periods and bring the others to me at the weekend. You must always be wearing them and I will get your wife to check, understand!" Nodding in acceptance of her orders, as I wonder what her twisted mind had next in store.

"Now tell my why you had an erection and I want the truth!"

" I saw people laughing at my wet patch and found myself getting turned on by the humiliation of it." Lying again hoping it would hide the truth.

":Well that sounds plausible as you are a pathetic excuse of a man. Don't worry there will be plenty more humiliation inline for you. So don't be surprised if your constantly hard. As long as Lynne wasn't to do with it, that's ok. On this occasion I will let it go but in future any erections must be reported to me immediately!

Now its time to put you to work, go and kneel by the sofa and wait for me there."

After she used the loo, she came and sat back in the sofa, opened her legs wide and beckoned me to her. Now in between her thighs she shuffled forward so her cunt was now completely accessible.

" Come on sissy you know what to do, I haven't wiped myself so it should still be nice and pissy for you, now get on with it!"

Diving back in and yes she was right as my face was immediately greeted with the remnants of her piss but I must admit it was quite enjoyable as her hairy muff envelope me and piss and cunt smells now filling my nostrils, my tongue set to work. I never thought id enjoy going down on fat women but in a strange way I do. This now made Lynne even more attractive than ever. God I wish this was her sitting in front of me, id pleasure her for ever! Anyway with my thoughts on Lynne, it made the job in hand more bearable.

With each orgasm came the brutal hair pulling and face bashing against her pubic bone, id be lucky to get away with a black eye at the rate she was dealing out this orgasmic punishment.

Again after another hours worth of orgasms she finally decided she was done and said she was going for a lie down and I was not to disturb her until I got the call from Sarah to go and meet her. However in the meantime I was to dress completely as a woman, makeup, wig and shoes! Ready for inspection when she awoke.

I again i was more than happy to oblige her command, as this was my wish how to be forever. Getting ready I was enjoying every minute as the transformation was starting to take place. Firstly I bathed and shaved my legs and any other offensive body hair. Now completely smooth, time to paint my toes and fingers nails. Tampon still in place back on with the towel and tight pink nickers. Then suspender belt and rolling the silky smooth black stockings up my legs, I was beginning to feel very feminine. Then finding my false breasts and securing them with body glue, saying one day I will have real ones. On with the bra I was in the right attire to start with my makeup. Emptying my makeup bag, now it was the decision as to which colour to use and as light blue was the fashion of the day, the choice was made for me, black eyeliner and bright red lipstick, finished the look. As I prefered the slutty look I went for a tight black mini skirt and white blouse.

looking in the mirror, even I was please with what I saw. Very fuckable crossed my mind. However at that time it was still a harsh reality that homosexuality was still a taboo activity in most parts of the country and discriminated against, especially with the revelation of ., homophobia was now reaching fever pitch.

So for bisexuals like me it was not advisable to reveal your true sexuality, which meant man on man encounters were few and far between but thankfully a bit more common in Mediterranean and North African countries, so made a good holiday destination for that little bit extra. Well that's enough of the history lesson back to the story.

Getting another bottle of wine out of the fridge and pouring a glass, I sat down at the table and crossed my leg on the chair, as my skirt rose up my thighs, revealing my stocking tops. God that's so sexy, I thought. Looking at my watch it was now 5pm and wondered what time the wife would ring, so I get rid of Tracey and just have a chill out. It was then I remembered I must phone Lynne but I would leave that for later when I was alone.

It did cross my mind, if I did see more of Lynne would I be introducing another woman to my complicated and pathetic sexual life? The few woman so far had very quickly lost interest in me as a sexual partner when It came to intercourse and many more before that because of filling my pants with cum due to petting. It could be said, they got a lucky escape.

My thoughts were disturb by a key in the door? iI was Sarah, saying as she walked in " where's Tracey? " Asleep up stairs" . " Don't tell me she knows already about your dressing"? I nodded. "God your useless and a total embarrassment. I am not even bother going to ask you" She then headed upstairs and I heard her say " Are you awake" as the door opened and again shut. After 10 mins the door opened and Tracey shouted down " 2 teas sissy, and be quick about it"

Taking the tea up and both women sat on the bed , their conversation was briefly halted as I was signalled to put them down and leave.

God I could tell I was in real trouble, no doubt my fate would soon be revealed!

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ladyboy44    23
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Fully dressed , I awaited the outcome from Sarah's and Tracey's chat but didn't have wait to long as both women headed down the stairs.

Sarah opened with the result of their deliberation and said " Tracey your new Mistress has made it clear to me that she has some use for you and I am more than happy she now takes control over your personal needs but I will still be in charge of any financial matters. Next weekend and any other time she requires your services you will attend her needs and all her commands will be obeyed without fail and I have said I will oversee there compliance under this roof. So to start with unless granted leave to do so by both of us, you will be dressed at all times except those hours you are at work and college. If I have real men here you will make yourself scarce, remaining in your room unless my door is shut. Understand, as failure to comply WILL result in your exposure! Now on your knees and smile for the camera."

After taking pictures of me they both headed for the door saying, we are going to the pub and Tracey will be back later as I still have some unfinished business with a man who knows how to treat a woman properly."

As the door closed behind them, I watched them disappear into the pub. Taking another very large glass of wine, my mind was buzzing and trying to digest what was just said.

Shit! My life and freedom was now being controlled albeit with bitter sweet consequences. However my wife does work shifts 2-10pm every other week so that does give me a bit of flexibility, I can live with that and thankfully that shift starts tomorrow. With that in mind I looked for Lynne's number.

Finding it I moved the phone to the window so I could see if anyone was coming to the door.

Dialing the number it started ringing what seemed for ages before a woman's voice answered. " Is that Lynne? " Yes was the reply, "'Hi Lynne this is Paul" .

" Hello lover boy, I knew you would call, I could see and sense your need. Am I right?"

"Yes you are right but I am in a difficult situation with Tracey and my wife, it's a very complicated scenario"

"Well you must tell me all about it, can you meet me somewhere this week?

"Yes I can do tomorrow between 5-9?"

" Excellent met me at the Crown at 6pm, it's nice a quiet in there"

"Ok sounds good to me and look forward to it!"

" Great see you then lover boy but I can't guarantee to keep my hands to myself. Bye for now!"

God what was I getting myself into? A wife, a Mistress and now a lover! How much do I tell her?

She already knows I cum easily and have a small dick, why should she be interested in me?

My thoughts were soon interrupt with a knock on the door , looking out the window, it was Tracey, letting her in, she barged past me and headed for the arm chair. " Get me a glass of wine" she commanded. Doing as asked and handing it to her. " Now kneel in front of me. I must say you do look pretty but we can't have that. I am not having a so called man looking prettier than me. I want you looking more like a granny. I will sort that out for next weekend! I am going to enjoy using you! "

"Sarah said she has a dildo in her bottom draw, now go and get it. I need a hard dick inside me! While your up there, remove all clothes and make up, just leaving your knickers and towel now hurry up! Oh yes on the bed Sarah has left you a present in a plastic bag, just bring it to me and don't look!"

Hurrying as fast as I could, I stripped and removed my makeup. Then I found the dildo, wow it was big and I had no idea it was there and grabbing the bag went back downstairs.

Handing her the goods, she just glared and shouted " Kneel sissy! I only look down on you from now on! " Then she rummaged in the bag and pulled out a pair of Sarah's dirty knickers . On closer inspection she said " oh yes their still damp with his cum stains, excellent."

Beckoning me closer, she arranged the knickers and slipped them over my head, so the crotch piece was in direct contact with my mouth and nose but could still see through the leg holes. Then as her finger started to push the material into my mouth she said. " Now start sucking sissy, I want you to taste real man's cum." !

As the aroma and taste of cum and cunt juices filled my nose and mouth I could feel my dicklet getting hard, as visions of my wife being fucked and seeded flooded my mind.

Happy I had got a good taste for her panties, Mistress said " tastes good doesn't it sissy"

"Yes thankyou Mistress and I must report an erection. "

"Well done sissy your learning. Now why doesn't that surprize me, so you like the taste of cum? Don't worry you'll get plenty of that but mainly your own.

However your erection is not of interest too me, now what is, is this, waving the dildo in front of my face. " open wide " as she pulled the panty to one side and started to push into my mouth. " Make it good and wet all over, understand! " little by little she inched it further into my mouth , until she reached my gag point, pulling back briefly but only to go back in . She seemed to enjoy my discomfort and retching and volumes of saliva was now being expelled down the shaft of the 12 incher. Happy it was sufficiently lubed, she withdrew it from my mouth and straight into her gaping cunt. " God that's better, nothing like a big cock to satisfy a girls need." Pulling the panties back in place over my mouth, she said come on you pathetic being this dildo isn't going to fuck me by itself", pointing to the large pair of plastic balls, Taking them in my hand I started to fuck her slowly at first but sped up at her commands. The faster I got the faster she rubbed her clit and in no time at all I was on the receiving end of her gushing juices.

Slapping my hand away and withdrawing the monster cock, she pulled the panties off my head and shoved them deep in her cunt. While she slumped back in chair as she rested from her orgasm. Some 5 mins later she opened her eyes, Looking at me she demanded "where's your panties? Oh yes I remember their inside me. Well slut you better retrieve them but mouth only! Now get to it bitch."

Diving in, my tongue flicked about to feel for them, I could just about sense them with the tip of my tongue but there was no way of hooking them out. " come on bitch what's taking you? Well maybe this will help, lie on the floor, here put these cushions under your head, " The next thing I saw was these two great thighs straddle my head followed by complete blackness as once again her cunt latched onto my mouth only this time her finger spread her lips and hole making it wider for me to get in deeper. When she pushed her pelvic muscles I could almost grip them with my teeth but just for I could she retract them! It was then I realised I was running out of air, I was being suffocated by her cunt. She kept pushing and retracting, as my hands were now slapping at her thighs for release and body wriggling trying to escape her vice like grip but she was far to heavy for me to push off!

Next thing I knew, she was slapping my face as my eyes opened, she then retrieved the sodden panties and mopped my face with them before putting them back over my head. "Sleeping on the job is strictly forbidden now go and stand in front of that mirror while I decide on your punishment."

After an hour I was still looking at myself but she had positioned herself directly behind me so in the reflection I was treated to a lesson in female masturbation using a dildo. There was no denying it was a turn on, as my little dickie was standing to attention. " Mistress I have an erection" !

"Turn around slut, I could do with a laugh. Where I can't see? Come here!

You call that an erection, my little finger is fatter and bigger than that thing! "

flicking it, followed by one almighty slap, which also connected to my balls , had my bent double in agony." That's for passing out on me! Now go and gather all you girlie clothes, panties stocking etc and put them in a suitcase and bring them to me."

Doing as told, I emptied my draws and pack it all in a suitcase and took them down to her.

"Right let see what you have?"

Going through everything, the only thing I was allowed to keep was a few girdle briefs, towel belts a couple of white bras and some tan tights.

"Next weekend we are going to some jumble sales and find you some more suitable attire. You don't need too look slutty to perform cleaning duties! "

"Right you can drive me home now"!

 

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ladyboy44    23
ladyboy44

Thankfully after dropping the Mistress home, I had the place to myself as the wife wasn't coming back tonight. At last I was free of those controlling bitches who had nothing else but content and humiliation on their minds towards me.

it was still relatively early and to be honest I was still horny as hell! I knew it would be a long shot but I thought I could give Lynne call and see if she wanted to meet up tonight?

Calling the number she answered straight away this time.

"Hi Lynne its Paul again, how do you fancy meeting me tonight?"

"Hello lover boy, you are desperate for me aren't you? How could a woman refused such a pretty boy. Where do you want to meet me?

" Well I can pick you up and we can go back to my place, it's safe all-night if you want?"

"You naughty boy! Well you better get over her as quick as possible then".

Giving me her address I got in the car and headed off to pick her up. There was just something irresistible about her, I just hoped I could be a better lover than usual.

Before I knew it I was knocking on her door, as I opened I was greeted by her beautiful smile as she quickly closed the door on her way out. Holding an overnight bag in one hand as the other took my arm saying "lead on lover".

Getting in the car, she leaned over and gave me a delicious wet kiss, I was so hard it hurt, it felt like I was now 6" and not 4! Her hand then lay on the top of my thigh. Squeezing it she said " come on then lover boy get me home, I know you want to fuck me! "

As I started the engine and head off, her hand stroking my thigh and hair as I desperately try to concentrate on the road. Then to my horror she leaned right over and unzipped my trousers and released my dicklet. Then with a quick look up and smile, she took my cock in her mouth. Why was it women had a knack of finding out my area of weakness and humiliation point so quickly?

Now fully encased in her wet warm mouth , her head slowly began to make little moves up and down as her tongue lapped and flicked my at my helmet. I'm not sure if it was her technique or my distraction of driving but I still hadn't cum yet? Under normal circumstances I would have cum as soon as her lips touched my cock but that's not to say the feeling wasn't building inside me. She just seemed to slowly induce pleasure without pushing me over the top.

As soon as I pulled up outside my house and letting her know we had arrived was the trigger for her to take my balls in her hand and increase the suction, sure enough 30 seconds later my cock exploded shooting a massive load of pent up cum in her mouth. Volley after volley but she lapped and swallowed the lot.

As the last drop seeped out and gathering it with her tongue, she finally got up and with tongue poking out I took it into my mouth. We kissed what seemed for ages , the she broke away and said " come on lover boy I need a drink to wash that tasty cum down.

Once inside I opened what must be my 4 th bottle of wine of the day. As I turned around to hand her the glass, I noticed she had seen the dildo and was admiring its size.

"hmm very nice size, I must try this out later. You'll help me with that won't you?"

"off course, it would be my pleasure" I replied and handing her the glass of wine. As she sat on the settee. As she patted the seat next to her I sat beside her. Once again her hand rested on my thigh, then she said. " Now you've got over your first load cum that should help you last longer but just to be sure I have brought a few joints of Moroccan Gold , its guaranteed to keep you from cumming. So lover boy you can fuck me all-night! Smilingly she pulled one from her handbag and lit it.

Sharing the joint I was soon becoming very light headed and almost emotive, barely able to lift my glass. Then she got up a stripped to her underwear. She looked gorgeous in her black stockings, suspenders, panties and bra. Ok she was on the large size and old enough to be my mother but that didn't matter, I was smitten.

"Do you like what you see?" She asked.

I nodded unable to speak. As she then unclipped her bra, releasing her massive tits and then leaned over me enveloping my face with her beautiful breasts. I tried to latch onto a nipple but she keep teasing me and bouncing them on my face.

Feeling my need to suckle, she straddled me and then lifted her left breast, giving her nipple a few tweaks it was now a solid as it slipped between my lips. As I sucked I felt baby like and content, helped by her pressing my head firmly into her mound of flesh.

I could feel her release the glass still in my hand and place it on the side table as she encouraged me to feel her arse cheeks but as she swapped breasts I felt her lift her buttocks as her free hand positioned the dildo to my crotch and then slowly slide down its length.

" omg this is awesome" she gasped as she adjusted to its girth and length.

" ohh lover boy what a big penis you have" she joked. " Now you hold it while I ride you"

With that she arched her back and started to rise up then down its length as my eyes were transfixed on her bouncing boobs. Her hands were using my shoulder as support as her thrusts increased. All I could now see was a bulk of quivering body flesh as my face lunged forward to dive into it, as her orgasm sent her into uncontrollable spasms.

With her full body weight now pinning me back in the chair, as her breasts pressed firmly to my face as my mouth finally able to lock back onto a nipple. Her hips were still slowly rising grinding and falling onto the dildo, saying " oh my lover boy, that was so good, I must get one myself!

With her hands lifting my head and clasping the back of my neck, I was now looking into those dark brown eyes and being drawn into her soul as she continued to slowly ride her new found toy. In a strange way and for the first time in my life, it felt like it was my own cock that was providing her such pleasure. As was the look of enjoyment on her face rather the normal disappointment that all added to my feel good factor.

She then leaned in for one of her special sloppy kisses. The saliva was flowing both ways as she would break off occasionally to smother my face in its viscous sticky strings with her tongue.

happy it was fully covered and with blurred vision she said, " oh just look at you lover, you haven't even undressed yet" with that she slipped off holding that dildo still deep inside her. " come on I want you naked now!"

Just about able to stand, I thumbled to unbuttoned my shirt when she said " oh dear it seems I have managed to wet another pair of yout trousers , it reminds me of our first meeting, so cute" looking down it was definitely drenched in her juices, the wife's going to kill me if she see's the definite stains which will result! ( Note to myself, soak them both later, they should dry before she gets back). Finally I managed to completely disrobe.

"' oh you poor thing, it is really small when soft but I think its adorable come here let's see if we can't make it a bit bigger." As she took it into her mouth once again. After 5 minutes of trying there was still no response, that joint had completely deaden my senses.

" Never mind we will try again later, but I am sure you wont mind helping me to another delicious orgasm would you?"

pointing to her now spread cunt, I knew exactly what to do as I knelt before her , she removed the dildo and placed it to her mouth and began to lick its length and suck the head. As I set about worshiping her completely bald cunt! Wow that looks so much better than the Mistresses hairy muff! At least I could see that delightful honey pot and clitoris, this was going to be a real treat. The wife's is trimmed but this was so so much better.

As I zoomed in on her nipple like clit, my immediate instinct was to suckle again and boy suckle I did. She was going crazy above me, as her hands clamped onto my ears. I could resist with my free hand to find her very wet cunt, as my fingers started to probe her depths as two three then four slipped easily in. Then I thought this can't be possible but what the hell lets try the whole hand? She was so wet it only took 3 attempts as my disappeared inside and her cunt entrance and clamped onto my wrist. She screeched in delight. " fuck! good boy fuck me! Fuck me!

With that, I push as far as it would go, as my fingers wiggled, feeling her amazing wet spongy tissue as it contracted and clenched at my every move. The harder I pushed the more she demanded, harder! I was frightened of hurting her but she insisted on this abuse . With my mouth still working her clit and fist pounding her cunt as her hands nearly ripped my ears off when her orgasm erupted.

As the last few twitches subsided she gasped. " You might have a small cock but you sure more than make up for it in other ways lover!"

Looking up at her but with my fist still in its rightful place, she smiled and just about managed to reach for her bag and retrieved another joint. Lighting it and take a few deep drags, as she leaned forward I started to withdraw my hand she said " no leave it where it is" as she then put the joint to my lips. Taking my share the numbness of my whole body returned but my head was floating in complete satisfaction as my eyes locked onto hers. It seemed I had a rock hard erection but looking down it was dead as a dodo.

As we finished the last few drags and my head now swimming in ecstasy we both must have dropped off into a deep sleep.

The next thing I knew was a tapping on my head, " Wake up lover, its morning" As my head jumped up, sunlight was shining on the curtains, " God what time is it?" I said, seeing my hand still inside her and from my position I couldn't see the clock. I slowly withdrew my hand with an almighty fanny burp. She laughed. As I ran still naked, my morning wood was raging and bouncing about as i looked at the kitchen clock. With a sigh of relief it was only 5 am.

"its 5, Lynne" I said, "what time have you got to be at work" she replied.

"9 so I have plenty of time."

" oh good, as you were such a good boy last night, it's time for you treat. Come here! "

As she got up and took hold of my cock then led me up to my bedroom, and laid on the bed.

" Come her lover boy" As I proceed to mount her. But the combination of a small cock and her body weight I could barely touch her cunt.

" Wait a minute" she said, as she put a couple of pillows under her arse.

"Now try" with the angle of approach more accessible, I took aim and felt some resistance as my cock slipped in. However still unsure if I hit my target I looked at her and said " am I in?"

"Yes my lover now come on fuck me"

As I started to pump I couldn't really feel her, maybe I over stretched her last night? It was only when she clenched down hard did I begin to feel her moist tissue. " How's that lover?" She said " Yes lots better thanks" as I continued my strokes but as I leaned down to kiss her, I fell out!

" oh you poor love, wait I have a better idea."

With that she turn over and lay on the pillows opening her butt cheeks as far as she could she said " Try this hole"

Wow a woman who likes anal sex, this was more my thing! Seeing her glistening bud and without hesitation, I again took aim and pushed in but this time there was a lot more resistance but thankfully with my cock well lubed with her cunt juices, i finally made the break through.

As I plunged as deep as I could go, she said " see that's a better fit, lover."

I must admit it certainly was and wondered if she felt the same pleasures I use to get when taking male cock in my arse. Although I never fucked a man myself at least now I could appreciate the experience of doing so.

Anyway as with each stroke my cock was soon nearing its tipping point and no sooner had it entered her it was shooting its contents deep insider her. It was all over in less than 2 minutes but still a record for me.

As I looked down and my cock began to slip from her but she squeezed her sphincter to drain every last drop. I could see a trail of cum was now beginning to leak from her tight hole and taken over by natural instinct i couldn't resist the need to tongue and lap at my own seed. So without thought, I spread her cheeks once more as I went straight into her and began to rim and sucking up any accessible seed. She let out a wince as I did so, saying "your a very naughty boy but don't stop" as I recognised the distinct movement of her hips as she began to masturbate.

With my face firmly wedged between her buttocks and tongue lapping up my seed. I had a free hand , so as she liked it so much last night my fingers started to probe her cunt again then my hand slipped inside again.

This time she screamed in delight and started shouting obscenities like" Yesssss lover, fuck me hard you gorgeous boy"! My first thought omg she's going to wake the whole neighbourhood ! Who cares, I was enjoying real sex with this woman. With that I just fucking pounded her pussy as hard as she demanded.

Sure enough he orgasm soon followed with more screams as her cunt gripped my hand her arsehole was giving up more of my buried seed and my face being crushed by her butt. This was heaven, finally a woman who appreciated my talents.

As she collapsed onto the bed, I released my hand and got up onto her back and massaged her shoulders to help her recovery.

After about 10 minutes I said " Did you enjoy that"? " God yes lover boy I could stay all day like this with you, if you want?"?

"Sadly Lynne I'd love to but I have a very important meeting at work today. Maybe another day when the Mrs is away. Anyway we better get dressed soon. I'll run you a bath if you want?"

" That would be great, thank you lover boy"

"Can we still meet tonight" ? "Yes of course, you can at last fill me in on all the details of your relationship with your wife and Tracy".

With that we both proceed to get ready for me to drop her home. As we pulled up outside hers she gave me one final lingering kiss, causing an erection, but that would have to wait!

" See you a 6 pm lover boy"!

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Lustman    405
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Wow! Amazing tale well written - love to hear more of your encounters

 

Lustman

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ladyboy44    23
ladyboy44

Thanks Lustman, appreciate the feedback. There's more to cum 😊

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ladyboy44    23
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All that day at work I couldn't stop thinking about Lynne, she was an amazing lover. She was the first woman that could really convert me. My real predicament was that how much do I tell her about myself? OK she already knows about my failings as a man but do I introduce another woman as to my preferences and end up a 3 rd knowing about my need to dress. At least my closest secret of my liking for men was still intact.

After rushing into town first to get to Boots to pick up my supplies of Dr Whites towels and tampax as instructed by my new imposed Mistress, I got to the pub early as I needed a couple of drinks before Lynne's arrival, to get my head straight.

With my thoughts swimming in my head, I then heard that distinctive voice from behind me. " Hello lover boy, have you missed me"? As I turned, she was all ready leaning in for a kiss. As soon a her lips touched mine, my cock was well on its way to another erection. God how does she turn me on so much? I thought to myself.

Shoving me up the seat, she sat down beside me. With her leading hand resting on my crouch. " Ooo I feel someone's pleased to see me, well sweetie I'm nice and wet for you also but silly me I forgot to put some panties on. I hope your not going to take advantage of that fact? Anyway get me a drink first and as I am in a pint mood, I'll have mild and bitter please."

"Of course" I replied but i thought she's definitely a man's woman, not often you see one drinking pints but fair play to her!

Handing the pint to her, I sat back down. As I did so her hand lifted mine to the top of her thigh, as she had a wrap over skirt, I soon found bare flesh. She wasn't joking either, she wasn't waring any knickers. God I love bare pussy on a woman"very rare"!

" Well lover boy that was a fantastic night, just what I needed". With that she gave me one of her erection making kisses.

Then saying "must get myself one of those giant dildo's. No offence to your " tiny tim" but I am on the large myself. You don't mind fucking my bum though do you? " No not at all, its unusual for a woman to like that isn't it"? I replied.

" oh you poor thing you still got loads to learn about sex. Don't worry lover I'll be happy too teach you. Anyway now you must tell me what's going on with your wife and where does Tracy fit into all this?'

"Well its a bit complicated but in brief, my wife and I have been married less than a year but she thought see could sort out my premature ejaculations putting them down to nerves but that combined with my small dick, has as she puts it "fucking frustrated" and has run out of patience. I know she had being seeing other guys for some months now but she has become more upfront and told me she is going to take any lover she pleases. It's that or she will leave me."

" ooh you poor sweetie, how can she not want such a catch as you? That's the trouble with young girls today they want it all and now! Tell her to bugger off , I'll come and live with you. "

Giving me a tender kiss and pressing my hand deep between her thighs. Oh god yes she was wet already. As my fingers searched for her entrance, she squirmed " Mmmm good boy, anyway how does Tracy fit on the scene"?

" To be honest im not really sure how that happened but again in short my wife thought it would be a good idea if I got more experience and as she works with Tracy I was told that I had to have sex with her to improve my manhood."

"Well tell your wife I will do that for you"!

" I'd love to but its a bit more complicated than that. They seem to have an agreement between and I have to go around Tracy' every other weekend for "Training" ! I can still see you without them knowing when the wife's away or every other week when she's on the late shift if you want"?

" I'd rather have you all to myself lover but I am sure we can work on that can't we?"

" I sure hope so" I replied, rubbing her clit this time.

" hmmm but in the meantime you be very careful of Tracy she's a real bitch! She use to beat her husband before he had enough and run off. Oooo god lover boy if you don't want me to orgasm in the pub, you better stop for a minute. Don't get me wrong I need too but I can't do it quietly. What time have you got to be back home tonight?

"Before 10.30 or I'll get twenty questions and she's already not best please because of my bad performance with Tracy!"

"You poor thing, it can't be easy for you , lets have another drink then you can drive me home where I have a little treat in store for you."

Now she really had me thinking but still conscious of the time , I quickly got a refill and as I sat back down. My eyes once more locked onto hers. I was helplessly being drawn into her soul, she had a power over me no ever had.

" You want me lover don't you? I know you want me, you need me. You want no other!"

it was is if I was being hypnotized.

" Yes Lynne I want you, really want you!"

"Yes lover, you are now my baby boy, now drink up, mummy wants to take you home".

I don't know what possessed me but I replied "Yes Mummy".

"Good baby" with that I downed nearly a whole pint in one go. A technique I learned from cock sucking and some deep throat!

As she took my hand and led me to the car. The spell was only broken as she pushed me to the bonnet and kissed me.

"Home James" ! "Yes my ladyship" I replied.

opening her door first and making sure she was comfortably seated before I got into the driving seat.

As we arrived at hers, I looked at my watch, still only 8pm. I had a good two hours yet before the witching time.

Opening her door," come on in baby" ! As I was ushered into the sitting room. "You take a seat over there", pointing to the settee.

Coming back with a couple of pints and a joint, I knew I was in trouble. Handing me my glass then lighting up, she took a few drags , then leaned to me and and gave me her blow back. Then gave me the joint to do the same. We did that until it was finished.

This time I didn't feel motionless but more alive, in need and dare I say desperate. She had already disrobed and was offering her breast and nipple.

"Come on baby it's feeding time" So without hesitation I assumed feeding position across her body and her arm supporting my neck as I did so.

Omg, milk started to flow as I sucked? Wow it tasted so sweet, I was latched and I wasn't going to stop until that breast was emptied.

After 10 mins it began to dry up. " Now the other side" she ordered and without hesitation I complied. After my fill and like a baby, she patted my back until the burb!

"Well done, you'll make an excellent baby. I knew you would like that, in the way you tried to latch onto my nipple yesterday"

" May I ask why you have breast milk or is that a stupid question"?

"No my lover boy that's not a stupid question, yes I have had a baby recently but since my husband fucked off, I have been a surrogate mother for couples who can't conceive .The moneys very good and beats working any day. The only side affect is my milk, so lover boy you've got a daily job too do. I can meet you lunch times if you can't see me later?"

" Sure why not, I'd love to see you everyday, no matter how short the time is and that milk is so sweet and beautiful, just like you"!

" Come here my darling baby boy"

With that she planted her lips to mine and with eyes open she gazed into mine as her tongue explored my mouth. My hand desperately searched for her honey pot, as she parted her thighs, permitting me unrestricted access my fingers soaked up her delicious juices as she opened up to envelope them. I still couldn't really believe she could take my whole fist, I know that meant my cock was of no use but it didn't matter as her arse was now my special hole and no need for contraception.

Sensing she was now flooded, I broke from the kiss and asked " will you sit on my face"?

" off course lover, anything for my baby boy"

with that, I lay on the floor as she lower her body onto my head , making sure my whole face was coated in her juices. God I love that!

Rather than suffocating me like mistress did, she was far more considerate and knew exactly how to position herself for her optimum pleasure. As she orgasmed there was a fantastic gush of juices, giving me ample to savor. She briefly broke off only to turn around so she now had access to my dicklet. Still allowing me to feed whilst her hand reached down to masturbate me.

As I was already highly charged, just a few strokes had me erupting with such force it was hitting her face which was hovering closely above .

As she squeezed out the final drips of cum, she turned to face me. Omg her face was dripping and as her hand was placed to my mouth, she said" look at the mess you've made! Now be a good boy and clean me up. That's with your mouth lover boy."

Without hesitation I made sure every drop was devoured.

" What a good boy you are but mummy thinks you enjoyed that a bit too much? You've done that before haven't you?

Looking directly into my eyes she awaited my answer. " Yes" I replied

" Don't worry there's nothing wrong with that but tell me honestly, has it been just your own, or other men's?

" Both" I replied.

" How have you got other men's cum"?

l couldn't lie, her eyes were able to extract the truth.

"From my wife's cunt and blow jobs"

" Ooo you are a naughty boy aren't you. Did you enjoy a cock in your mouth?"

"Yes"!

" I can understand that, have you been fucked?"

"Yes"!

"How many times?"

" Many, so many I can't put a figure on it"

" oh my you are a dark horse, my baby boy likes it both ways! You know your going to tell me more, don't you! If I helps I like women too"

"Yes I will tell you because I know I can trust you and dare I say, I love you. However, reluctantly I better go or I'll be in trouble with the wife.

" Oh must you sweetie? Stay the night with me. By the way does she know about you and men?"

No she doesn't, no one does apart from the other men, I've been with."

"Don't worry sweetheart, your secret is safe with me, just keep me happy, as I know you want too. So you'll be keeping warm tonight won't you?"

" Shit what the hell! Yes I will, she doesn't care about me anyway"

with that she hugged me, then a very very passionate kiss. God I was hard again. This woman is going to get me in real trouble but I will worry about that tomorrow. For now I'm just going to enjoy the moment ! I'm falling in love with a real soul mate and tomorrow's another day!

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