That cold December of 1981 was about to change my life in so many ways

 By chance I'd found out my girlfriend wasn't as isolated as she'd made out when we were all snowed in,  she could have come back two weeks earlier if she wanted, the black and white photos she'd carelessly placed  of her with her former boyfriend in her flat  taken in a photo booth in Woolworths was a real eye opener, 4 consecutive black and white photos passport sized, both smiling like starstruck lovers was painful to see, in one, his hand pushed deep inside her blouse and smiling down the lens of the camera as if making a statement towards myself if I ever saw them.

 The rumours were true, her ‘ former ‘ boyfriend was a black man , tall with long dreadlocks.

How could she do that to me as I briefly took the  moral high ground only to be brought crashing down to reality as to what I'd done, oh the hypocrisy! 

We tried to reconcile for  her misdemeanour, to the point of desperation from myself declaring I'd be willing to share her with him as I really didn't want to lose her.

Thinking  about it now, I think that was my first inkling of being a cuckold, a medieval word  I'd never heard of back then or its meaning but she'd  drag me helplessly into a world of depravity and submissiveness that I was forced  to accept much later.

Well things didn't go well and we split, her going back down to her parents and him.

That would be my first disappointment as a few days  later disaster struck as the pipes burst at my landlords and made the house unliveable leaving me potentially homeless, that's when John came to my rescue.

He offered me the room I'd used when I was stranded  on a more permanent basis but there'd be conditions, ones that would greatly benefit him, and ultimately unbeknown to myself, his close circle of friends.

I really wasn't in a position to refuse, it was still bitterly cold with snow still on the ground and I had nowhere to go, cautiously I accepted not fully knowing what his ‘ conditions’ were to be.

I guess you could say John was my knight in shining armour as he came round and helped me pack my things, he was more than curious as my landlord bid me farewell with a lingering hug, yes, I was also in a sort of relationship with him, a sweet 70 year old who really looked after me if you know what I mean, I just seemed to attract the older man.

Once back at his place, I unpacked, very quickly I was to learn what his conditions were but by then it was too late, I'd no where to go and he took full advantage of that fact.

That night would be the last time whilst I was his lodger that I'd have the outwardly appearance of a nervous young man for tomorrow I'd become Christine for all and sundry whilst in the confines of his flat, I thought I'd be spared the embarrassment at work  but most of the women instinctively knew and made comments like ‘ when's the wedding and oh my, it doesn't show , patting my stomach, they knew all along that John was  Interested in me, It was all in good humour if not embarrassing all the same.

That first night was uneventful apart from being unable to get to sleep, thoughts of my ex girlfriend, then John but most of all listening for that dreaded knock at the door , I hadn't forgotten Jeff! The last thing I needed right now was him trying to fuck me back into oblivion, it took days to recover from what he did to me last time.

Next morning it was back to work as usual, we arrived together which raised a few eyebrows from some of the resident Neanderthals and smirks from the ladies , especially Debbie who'd snogged me in the stationary cupboard at the office party.

There was something about her I couldn't quite put my finger on, over time that finger would end up in ‘places’ I'd never even contemplated.

It was difficult but I managed to survive the day as John and myself went home like a couple, there was no physical contact between us but our body language said it all.

Once home, John suddenly went all serious and told me my ‘ terms and conditions'

1 . I was to be dressed as a woman at all times whilst in the flat.

2 . I would share his bed as his lover whenever he saw fit which was most of the time 

The third was the one that had me looking at the door I'd just come through , this was the biggest ‘ requirement’ that made me nervous.

3 . I'd be available to his friends and guests at any social gathering held at the flat if and when required.

Given that Christmas and new year was fast approaching there seemed an inevitability that my presence would be required at these events.

Well, I'd been fucked by Jeff a couple of times over my brief stay but the thought of him having access to me whenever was a scary thought but then again, I was living rent free so perhaps I should give this new experience a try, I mean, what could possibly happen within the safety of John's flat?

John showed me my new wardrobe, a mixture a some of  his wife's old clothes and some new ones, some still in their cellophane protective wrapping, her other clothes which were either torn or spunk stained were noticeably absent, it would appear John had been prepared in the hope that there would be a possibility of me moving in on a more permanent basis, it was more down to when the opportunity presented itself, he was so close those 2 days when I was stranded at his  but now the opportunity had unexpectedly presented itself as if  it was meant to be and an opportunity he was going to exploit, I wasn't going to be that little fish slipping through his fingers for a second time.

John said I had free range on what I could wear to express myself but on special occasions he'd dress me to ‘satisfy his little fetishes’ or for his guests he jokingly said, I thought he was joking to make me feel more at ease but I was at the time blissfully unaware what would be expected of me that new years eve.

The first few days were the best I'd ever had, I could be dressed and not be judged oh that freedom felt so exhilarating and John loved the way how I'd taken so quickly to always looking so pleasing for him, however, there was a problem, doing my makeup and just a simple thing of putting stockings and suspenders on.

For those of us who first tried to wear them will know of the struggles to clip the straps to the top of the stockings and not to ladder them in the first place!.

John suggested he send a friend round whilst he was away all day on business who'd help me with my shortcomings in feminine lingerie and makeup application.

The next morning John left for his business trip, he'd not be back until 6 but I was to expect a call later for some girlie training as he put it.

Slipping  on one of his ex-wife's floral knee length dresses and satin panties I was ready.

A knock at the door sent my heart racing as I went to open it, that's when I got the shock of my life, it was Debbie!

I wasn't aware that he and Debbie were friends of sorts but there she was, looking me up and down taking in her first sight of me as Christine.

‘ mmmm, not bad but we can do better’ as she came in carrying a  case showing little interest in me.

 She sat me down in front of the dressing table and opened the case. It was essentially a beautician's mobile workstation. Right, let's see what we can do’ as she leaned deliberately? Over me, pushing her large warm soft tits into the back of my head and neck, now I felt what I could have had at the office party being pushed into me, what a  missed opportunity for a horny young man when she was offering herself to me.

‘ this will have to go for a start ‘ as she pulled at my curly hair.

She led me to the kitchen and sat me down, putting a shawl over me then the sound of some clippers, I panicked, John never said anything about this, Debbie sensed this and explained it was necessary so that my wigs would fit correctly.

I could have cried as my curly locks fell to the floor, fortunately Debbie was also a good hairdresser so I didn't look too bad when she'd done.

Looking at my toe nails disapprovingly said ‘oh no these just won't do, no wonder you keep laddering your stockings’ she was right my toenails were protruding a bit, no wonder I was laddering my stockings! Once done she held up two small  bottles ‘ which colour’ she asked, I pointed to the red as she went back down to my feet and painted my nails. I can still remember the smell of the nail polish  as she expertly painted my toenails. 

Next was the make up, she did my eyelids in a shade of blue , next my lips into a shade of pink and to finish off the black mascara making my eyelashes thick and firm too. 

A mousy brown long wig was placed on top of  my newly cropped hair, a perfect fit, last but not least my finger nails into the same shade of red.

What do you think she asked as I looked into the mirror.

Looking back at me was a beautiful young lady, the transformation was incredible, my young complexion really made my whole look believable which would become my nemesis as men would find me irresistible, especially John's friends.

Then the most complicated issue of putting on my stockings and suspenders.

She ordered me to raise my dress and take my knickers off as she showed me in unnecessary detail how to put the black and red satin? Suspender belt on.

That was the most embarrassing but the most erotic feeling ever as I hitched up my dress and slid my knickers off, my obvious excitement was plain to see as my cock, now marginally bigger in its development sprang out with such force right before her eyes, as exciting as it was I just wished the ground would open up beneath me as I guess my sissification came to fruition. First the suspender belt which, again, fitted perfectly, then the stockings which she deliberately took her time to slide my feet into and roll each one up my hairless legs, I watched intently as she fastened the straps to my stocking tops, I think her attention though was being diverted to my hard young cock twitching away close to her face.

‘ oh my, we are a naughty boy' flicking the tip of my hard cock which miraculously went soft! 

Debbie displaying she was  most definitely an experienced woman in this sort of thing!

With some slight adjustments of the straps she told me to stand up and  to put my silky knickers back on, I can still remember the feeling as they effortlessly slipped back up my  satin stockinged legs, last but not least she taught me how to walk more like a woman, that was the first time I experienced just  how smooth and sensual it felt as my legs brushed against the dress and an instant hard-on pursued totally ignored by Debbie, was she deliberately teasing me or were my hormones playing tricks with my body as I now confidently walked around the flat under the watchful eye of Debbie.

‘ I hope you were watching as next time you'll have to do it’ suddenly my euphoria was extinguished as reality kicked in. Don't worry she reassured me, it'll come to you.

The final piece of the puzzle was the high heels, maybe 4 inches , training shoes she quipped as I put them on, a surprisingly good fit, John really has been paying attention!

Debbie stood me up and with me holding onto her, walked around the flat, women make this basic task look so easy, for me I wobbled around clinging on for dear life, after 5 minutes I seemed to grasp the concept of being able to stay upright, then it happened as I stumbled and twisted round facing Debbie and falling into her  massive womanly tits, an awkward moment then she just said it.

‘ you've spent a lot of time looking at them at work, do you want to play with  them, you could have last time but you were too shy ‘

Errr, young horny sex mad young man here!!

She unbuttoned the top of her blouse and pulled a tit out  of her white silky  bra and offered it to me, well I'd done it to my now ex but hers were tiny in comparison to Debbie's, a voluptuous middle aged woman with quite a shapely body and tits  to die for.

With some hesitation I went in and sucked on that succulent nipple presented to me into my mouth, as soon as I made contact she put her hands around my head and pushed  that nipple into my mouth, this I wasn't expecting at all as she ran her fingers through my newly acquired long hair, she didn't say much as I tried desperately to adapt to this new situation as she pulled her other tit out and playfully pulled my head between them, I can remember the heat against my face and the feeling of her heart pounding excitedly away as she crushed them into my face.

I was now in a state of confusion, do I carry on, bearing in mind she was another work colleague, tongues would certainly wag if this got out or pull away and stay loyal to John.

Well my hormones took charge  as I now started to explore this more mature woman offering herself to me, I'd be a fool to refuse her.

She unbuttoned her blouse to reveal the most wondrous sight as both her tits hung down towards  her firm rounded belly over the top of her bra, I just stood there in a daze looking at her magnificent huge tits, Debbie fumbled round the back of her bra then removed it from her curvaceous body, they dropped down to her waist like they had lead in them, nice juicy ripe tits for the taking, and taking i did as I used all my limited knowledge to caress and kneed them as I had my girlfriend's but these were more sensuous and erotically pleasing as my cock went for broke and pushed against my dress restrained only by my knickers.

Debbie was playing a dangerous game and was about to reap the rewards as she led me by my hand to the bedroom.

I don't know if it was by chance or deliberate but she led me into John's room, maybe to prove a point to herself as she seductively laid herself  on the bed, now topless, I just stood there lustfully looking at her sexy mature beautiful body before she quietly told me to join her.

Well, that really was an offer I couldn't refuse, that feeling of letting John down was totally eclipsed by the urge to be with her but me dressed as a woman, how was this going to work? 

I was about to learn a new lesson in life when it came to sex as Debbie slid her skirt down her large womanly hips to reveal a nice pair of salmon coloured panties with a very obvious wetter patch, again this was a first for me as she grabbed my hand and placed it on her mound, holding it as she pressed it against her sex, it was like she was giving me instructions which I picked up very quickly as any inhibitions quickly dissipated as my own excitement grew.

I traced a curious finger across her panties until I found her inviting slit, now wet with excitement, tracing it down its full length and back.

Now that really pleased her as she let out a loud ‘ Ahhhhhhhhhh’ as she released some of her sexual tension, mine however was building and creating quite a mess in my own knickers.

Things now really started to heat up as she lifted her hips and slid off her panties to reveal to me for the first time a mature pussy, its lips prominent and puffy, again, this was my first time but they were certainly the largest I'd ever seen as my inquisitive finger went between them and into a very moist pussy, now I had Debbie's full attention and her mine as I explored that warm moist hole.

One finger wasn't enough so I tried two, Debbie didn't even acknowledge the fact so I tried another, now things were starting to happen as her hips rose to meet my fingers , then I really did take a chance, one I thought I'd never accomplish as I wormed in another finger.

Now I was in new territory as Debbie responded, a woman over twice my age enjoying my fingers inside her, however she had plans for me that would really open up my world of intimacy with another woman, the sounds Debbie was now making were scary as I'd never heard a woman make them whilst having sex although I must admit my experience with women at that time was extremely limited.

I was quite pleased with myself that I could actually do this to a woman and a mature one at that!

Then, she made me do what I thought at that time,the most disgusting thing as she told me to go down on her.

I'd not even done that with my ex so I really struggled as I reluctantly got into position, a part of me was saying NO but oddly the rest of me was saying Go for it, a confusing moment as I placed my head a few inches above that incredible mature neatly trimmed pussy, its musky scent intoxicating as I closed my eyes and lowered my head and nervously stuck my tongue out.

That first touch wasn't as disgusting as I'd feared, it actually tasted ok, her juices so sweet and intoxicating, I had to have another go , oh my, so so sweet as I now lapped away like a puppy which sent her into another climatic moment as her legs clamped around my head, now my tongue getting more familiar with her moist pussy, it explored more as I lapped at the top part, suddenly my tongue touched a pronounced lump, unwittingly I'd found her clit, that first touch sent her absolutely insane as she screeched out my name and pushed my head hard against her, her legs clamped so tightly against my head I was finding it difficult to breathe, I wasn't sure what to do, I'd never experienced anything like this with my now ex as I now struggled to get my breath. Still being a novice at this I wasn't sure what to do.

Debbie released  my head from her vice-like grip allowing me to  try again  with the same amazing response, there and then my bisexuality had been validated by a most special and sexually frustrated plump middle aged woman, a preference I have to this very day! and I owe it all to her, in effect, my first BBW.

What happened next was the most amazing sexual experience and I'll admit, I had very little experience of women compared to men back then so a very steep learning curve for me, and more importantly, a most enjoyable one as she laid flat on the bed, her huge breasts hung each side of her beautiful body as she invitedly opened her womanly curvy legs and placed her hands each side of her mature pussy and opened it up for me. I'm not sure if I was scared or intrigued by the sight of a mature woman's pussy being stretched open in such a way in front of me , moist and ready for a really inexperienced young man to try and fill.

Debbie joked ‘ we'll go on, it won't bite’ I sort of laughed nervously as I contemplated doing the unthinkable, making love to a woman more than twice my age but my testosterone fuled body was screaming at me to fuck her, i couldn't resist that, I mean, who could?,  finally I succumbed to the calling.

She  ordered me to remove my now pre cum wettened panties and get back on the bed, my cock  now hanging down below the hem of my pulled up dress.

‘Oh Christine, please fuck me , please’, there was definitely an air of desperation in her voice.

I looked round for a condom, grabbing a packet, she just placed a hand over mine and told me I wouldn't need one and not to worry, well how do you not worry! But that animalistic urge that had slowly built  up inside me was about to get the better of me as I positioned myself back between her legs, my horny unsheafed prick only inches away from entering her,  my ex would never allow this so definitely a first and boy do I remember this, it felt absolutely fantastic as my cock touched her stretched out pussy lips, her reassuring voice of experience saying to take it slowly, I guess she didn't want me to go off prematurely.

She needed to be  in control, which I was actually enjoying as she came down from that climax.

 I went to remove my dress but she stopped me , ‘ No, I need you as Christine’ as she pulled my dress up to reveal a more ‘ mature’ rock hard cock pointing directly at her, it's wet slimy pre cum soaked head glistened in the light.

A smile grew across her face as she had finally got me in such a state of excitement, I'd not be able to hold myself back.

With some hesitation I took a deep breath and put my cock at her entrance, it felt warm to the touch of my glans as it nestled motionless against her.

The next thing I remember was how it sank effortlessly into her as my hips pushed my cock into her

That moment as her pussy engulfed my hard and eager cock so easily it actually felt amazing, the warmth of her mature vagina wrapping itself around my bare skinned cock, un-sheafed, moist  and very accommodating as our hips met.

Well I've fucked a woman before so this would be the same ? WRONG! 

Unlike my ex, her pussy walls allowed me to effortlessly slide back and forth with very little resistance, Debbie closed her eyes as I tried to fuck her as she'd dreamed of but my still maturing cock was no match to what she'd probably taken in the past as I started in earnest to make an impression into what was a cavanus pussy for my little cock.

That feeling of her velvet like walls hugging my cock lovingly, encouraging me to do more of the same as I tried my utmost to please her, looking at her body, especially her tits as they now moved in response to my tentative thrusts as I savored every second of actually fucking this amazing woman, watching every move she made, those amazing breasts captured my intrest as they now started to wobble about, that just made me thrust that little bit harder but really not making much impact into her more well used  pussy.

 I just wasn't aware just how demanding she'd be as I now ploughed away into her, some sounds of satisfaction encouraging me to go faster, that would be my undoing as her breasts now lurched out of control as she dug her nails into the arch of my back.

My orgasm really caught me out, I could feel myself building up to the moment but had no idea I wouldn't be able to control it as Debbie ran her hands down my back , her eyes closed as she softly stroked away , then it happened, I wasn't expecting to lose control so quickly as my cock now frantically pushed away inside her,  she cried out as I guess she came, she cried out a name, not mine, it was John's ex wife's! That was the exact moment I lost control imagining Debbie with his wife, that one thought did it as my legs straightened and stiffened, my cock felt strange, unsheathed inside her as it went through its final throes and went off like a cannon, her eyes opened wide with the sudden realisation that a man barely 20 had shot his spunk , unprotected inside her, for me, initially it felt fantastic, my sperm now flooding into this beautiful woman, her legs now wrapped round me as several firm jets of young virile sperm found its  way into her receptive body, unrestricted by the usual condom I'd normally had to wear, this was my first insemination of a woman, that feeling as my sperm shot out my pulsating shaft and Into the depths of this amazing woman unrestricted.

I was lost in the moment, what I'd just done not registering as I collapsed, exhausted on top of her soft warm breasts, our hearts beating frantically against each other's chests.

I tried to pull out but she wouldn't let me, the remnants of my powerful ejaculation still oozed into Debbie's warmth moist depths, her pulsating virginal walls effectively milking my satisfied cock of every last drop of sperm.

Ok, I'd enjoyed what I'd just done, then realized what I'd done!

How could I have been so stupid, what if John found out?

Debbie really was a tease as we both sat up on bed , her chest bright red and both breasts hanging down with the most amazing hard red cherry nipples, I covered myself up with embarrassment not believing this attractive older woman allowed, or should I say, wanted me to fuck her so badly.

Some very awkward small talk ensued, in the bedroom mirror I could see just how red my face was as she more or less teased me, her fingers now inside my dress, finding my slightly larger than normal nipples and tracing it down to my semi erect cock which miraculously swelled to full hardness, for a moment I thought she wanted another go with her newly found stud muffin but she just smiled at me and flicked the tip of my new found erection which really hurt but had the desired effect as it wilted.

‘ maybe another time’ she said, what a fucking prick tease! 

She got out of bed and collected her clothes and went to the bathroom whilst I just lay on the bed, trying to take in what had just happened, my eager cock yet again poking up inside my dress.

10 minutes later she emerged looking more radiant as she came and kissed me on the cheek, then a finger to her lips then mine ‘ our little secret ‘ 

With that she made sure my makeup was ok for John and just left as if nothing had happened leaving me in a complete daze.

It would  be a few more hours before John arrived home, one look at me was enough to be dragged back into the bedroom for the second time! 

For him it had  been a difficult day and I guess he took his frustrations out on me, the sound that mattress made sounded like he was about to give up  the ghost as he ploughed deep into it, he didn't last long as he let out a loud roar then an Ahhhhh as he thankfully came, that familiar warmth entering my body before withdrawing from me and turning me over to reciprocate by wanking me off so he could watch me ejaculate in my usual powerful manner, thankfully being young I was able to recuperate very quickly and did managed to shoot a steady stream out not as powerful as I usually do but how could I tell him I'd shagged  his friend only a few hours earlier, thankfully he never found out although Debbie would return for a second helping when she knew John was away on business.

I had no idea where this was going but  new year's eve would answer that in such a way I'd question myself over how I perceived my own sexuality and what direction that would take.

The days leading up to New year's eve were pretty tame, John had me all to himself and treated me well , the sex between us was nothing short of magical, his interest in my nipples got more intense as he'd put my nipple suckers on regularly, increasing the length of time they were on, in effect, stretching my nipples into large hard cones. Up to now it was the best Christmas I'd had in a long time since I'd left my estranged parents, John even treated me to a new wardrobe although he did choose all the outfits, the lady in the sex boutique shop gave us a good look when John held various items against me to see how I looked but I guess  this was a shop that was used to shoppers like ourselves so we're most helpful, if not slightly perplexed and curious as to why a young man was being taken shopping by a man over twice his age but I guess they'd seen it before?

Christmas is a time when gatherings happen and John was no exception as his  friends came and went, some just to see John's new friend, I guess some were hopefully seeing if they could try me out so to speak  like a new toy, John kept me close , he wasn't going to share me with anyone, well that was until new years eve where a small gathering of friends got out of control and…….. well, I'll leave the details for the final installment.