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Surprise new beginnings

"Pauline finally makes a honest woman of me"

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It's now 18 months later and quite a lot has happened. First and more importantly my relationship with Pauline was as strong as ever, my past demons now  banished thanks to Pauline's intervention. Steven and Gary had got back together and we're back on talking terms which I was genuinely happy for. My body shape had changed, that clinic offer from Pauline? My choice was obvious as I now sported  a good looking 34b bust, hair now black,  halfway down my back and a good size 14 with curves in all the right places, yes, Pauline really set my feminine side free, yes, I was now truly happy at last and of course, Pauline spoilt me rotten!

The hotel was now refurbished, she hadn't initially told me her plans but her vision was now paying off, A country hotel where crossdressers and transgendered people could come and stay in a totally relaxed environment, it had its own boutique where you could get advice and more importantly, have a makeover aimed at  those just starting out or unsure how to apply makeup , word got round unexpectedly quickly as it was a roaring success, other hotel chains were starting to take notice  

Of the concept but not before Pauline registered her hotel ‘ theme ‘ and created a franchise. 

Yes , these were exciting times indeed.

To celebrate her success, Pauline decide to hold a dinner party in the restaurant for our friends and businesses partners who'd helped to make all this possible, 

At that time I had no idea she was to make an announcement, a life changing one in fact, until that night I had no idea, neither did our guests, that was typically Pauline!

The night of the dinner party both Pauline and myself looked exquisite in our dresses, by now I was 99% passable thanks to  Pauline. We walked into the hall, heads turned to watch as we both gracefully made our way, with the help of one of the waitresses to our table. 

The table layout was rather odd, they more or less formed a semicircle our table in the centre  , I guessed for speeches to the guests. All went well, Pauline got up and made a speech about her new venture , a few others involved in the venture made speeches and congratulated Pauline for her successful venture ,then there would be a toast to the host. Instead of coming back to the table , she remained in front of everyone ,holding her arm towards me. She just said my name to join her. Nervously I looked round, all eyes were on me, I hadn't written a speech so, unlike some of our guests, I was totally in the dark. We stood together, it was no secret we were a couple so I didn't feel awkward, then one of the waitresses tapped a glass, a silence descended over the room, so quiet, I bet you could have heard a pin drop in the next room!, something important was about to happen and I had absolutely no idea what.

All but the lights above us went out, now I was panicking, what was she doing? , then the totally unexpected as she faced me and went down on one knee the best she could in her dress.  Holding a small box with a ring in it looking deep into my eyes   ‘ Christine, would you do me the honour and marry me’ Time seemed to slow down, I couldn't believe what Pauline had just said and done, one look into her eyes was all it took for my reply, ‘ Yes……, yes I will’ Everyone stood up and gave a thunderous applause, then the congratulations. I couldn't believe what had just happened! The rest of that evening was a blur, thank heavens someone recorded it as I watched that moment over and over again still in disbelief and quite tearful.

Now It was time for wedding plans, Pauline had already set the ball rolling and between us , we'd plan the wedding, one everyone would remember.

Bridal dresses were a tricky thing and we both spent hours looking for that ‘one dress’ impossible! Then I hit on the idea of having one made, she was surprised I remembered the first dress I wore when we first met, an asymmetrical dress, Pauline was very excited with that, a dressmaker from London was employed to make it ,out of satin . She wasn't doing anything by halves. With that wedding plans were made , then Pauline ,out of the blue said i should have a hen night for myself, a last night of freedom she laughed. I know that laugh! She'd planned something, it would be at a private sauna and massage for myself, a pampering session for which I got then I expected. That would be a night to remember, a free pass she said. By now I wasn't interested in that side of things but as usual, I'd soon be at the centre of attention of another couple with her blessings.

To be honest I really wasn't interested in going but Pauline insisted, her only words of warning was ‘becareful, I don't want you walking down the aisle like John Wayne’ . She realised what she had just said and we both burst out laughing, we both saw the funny side as we often would.

Now everything was in full swing, booking a venue with a hotel was very straightforward! My measurements taken and the dressmaker was busy making a masterpiece.all this hustle and bustle kept us busy , then my party was upon me. 

I dressed conservatively in just a blouse without a bra, cotton panties and jeans. I mean,what do you wear to go to a sauna?

Arriving at the sauna I was met by a couple , a man and a woman both in their mid to late 30’s, extremely fit in every way!, they introduced themselves as Amy and lee, they'd be looking after me they said as I was guided to my cubicle to change. Quickly I undressed and wrapped the large white towel around me, I opened the door and I was led to the hot tub, softening my skin before my massage Lee  said . Dropping my towel I was laid bare, their eyes taking in every inch of my body, I could have sworn I saw Amy licking her lips as she checked out my breasts.

Stepping into the hot tub to the background sound of classical music Amy in a bikini and myself sat in whilst Lee in tight Speedos got us all some champagne. Now all sat together we sipped our drinks whilst we chatted, the conversation soon came round to my breasts, I guess Amy was more interested in them than she let on, lee didn't sound fazed about my appearance either. I'd been ordered by Pauline to take a tablet which was having some effect, I tried my hardest not to get an erection but Amy's breasts did look very tempting squeezed into that tight bikini top, so much her nipples created their own landscape as they stood out, physically, through the thin material. It was clearly obvious what was on Amy's mind, Lee? I wasn't so sure but I think the temptation of my lush, but hard pointy nipples got the better of Amy, ‘ ‘may i’ she asked politely. Well I had a good idea I'd be ‘ played with’ whilst here so I held her hand and placed it on my breast, Lees eyes looked like they were about to pop out as Amy's hand softly cupped my breast, I removed my hand, Amy's was still there so her fascination was validated. My nipples were still my Achilles heel, Barry's legacy, when it came to sex as Amy was about to discover just how much, her fingers tweaked my super sensitive nipples. I think my reaction caught her off guard as I pushed backwards against the side of the tub. Lee seemed frozen, not quite sure what to do as he watched Amy now teasing the tips of my nipple. Surely this couldn't be his first time? the signs were there but in an act of reassurance, I held his hand and placed it on my other breast, I think he was still processing the fact I had nice breasts, through the water I could see a now distinctive bulge in his Speedo's, a very impressive bulge from what I could make out. From there on, I closed my eyes as these pair caressed, and tweaked away at my breasts. Here I was in a pool with another man and woman , my body had  enslaved me as they momentarily turned me back into that slut, I wasn't expecting this but I'm ashamed to say I was REALLY enjoying it. Amy stopped momentarily to remove her bikini top, fairs fairs she said as she removed it , her curvy breasts now revealed. ‘ here, let me’ she said as she placed my hand onto one of those luscious breasts , now we were both kneading , squeezing and gently twisting each others nipples, my other hand was now guided between Lees legs, I was so lost in myself that I didn't see him remove his Speedo's, I instinctively grabbed his cock, his response was similar as he grabbed my cock , hard now , not with just the tablets but the whole situation I was now in. Amy went in and started to greedily suck away at my now hard protruding nipples as Lee now slowly wanked me off with me reciprocating. It had been a long time since I'd been in this position, Pauline was more than enough for me but I guess this was a one last time scenario which had Pauline's signature written all over it!. Amy's attention made me as horny as fuck, so much I think I may have gripped Lees cock a little too tight as he cried out , his response was equally painful as he pulled my foreskin all the way back revealing my swollen purple glans , hmmm nice I thought to myself as he continued to pull hard against my foreskin. Amy was now really into my breasts as she sucked hard away at them , lee was showing signs he was about to lose control, to be honest I think I was ahead of him, all the attention they were giving me was far too much for my body to cope with,  I think this was their plan all the time, I just couldn't hold back any longer and believe me I tried. My body tensed as my inevitable ejaculation built up inside my now swollen cock, then something happened I'd never experienced or witnessed before, as Lee brought me to an earth shattering orgasm , I watched myself ejaculate into the water, not jets of sperm as I'd expect, as my now pulsating cock started to ejaculate, but  a white string of sperm  shot into the water and momentarily suspended before it slowly sank. My cock pulsed again and again as more of my sperm was ejected into the water. Lee quickly scooped it best he could into his hand then rubbed it into my breasts, paying particular attention to my nipples, tweaking them  once he'd rubbed my own sperm into them. I just couldn't believe what had just happened, closing my eyes I wanted more but was soon brought back down to earth as Lee said ‘ right , let's get you cleaned up before we do your massage’ they helped me out of the tub and into the shower so I could remove all traces of my own cum. Once in,they left the room, presumably to prepare the massage room, I  started to soap myself, I heard the door behind me open and thought it was Lee just popping in to collect something so carried on, the next thing I knew was a pair of hands around my breasts, slowly rubbing body  wash over my still hard sensitive nipples. Lee must have thought about ‘ helping me ‘! The sensation of his hands over my erect nipples as he slowly circled both of them simultaneously with a finger was just too much for my body to handle and just sent me over the edge, I lent forwards against the shower wall, taking my chance I pushed back to feel a cock, now jabbing into my bottom. The hands continued to play with my breasts , then lower down, having not long cum I couldn't muster more than a semi hard on, the hands went back to my breasts , then a kiss on the back of my neck as a hand pushed me forwards into a more ‘ accommodating’ position. Now pushing my legs apart with his foot I felt his hard cock against me, with the shower gell he rubbed some over my crack and some on his cock, then with some careful adjustments his cock found its intended target as his cock slipped in, using shower gel for lubricant may have been effective but it stung a little, mind you I think that masked the pain somewhat until he was fully inside me. The feel of this Cock felt somewhat smaller than the one I'd seen earlier in the tub. Suddenly I realised it wasn't Lee! Who was this mysterious man?

Well whoever it was, certainly knew how to make love as he now fucked me. So here we were, coupled together in the shower, warm water running down my back and between our bodies, no doubt helping him easily slide his cock, now effortlessly into me. It wasn't a long graceful fuck, more of an urgent need to inseminate me before he was discovered. The last minute was confirmation of that as now each inward push into me would be more of a jab, some of them powerful enough to lift me momentarily onto my tip toes  until he was about the cum, there was no mistake with his climax , with one final barrage of  loud grunts and violent thrusts, he came, oh that wonderful feeling of a throbbing, twitching cock spewing it's hot seed into me. At the same time he squeezed and pinched my nipples  so tight I cried out as he pumped what he could into me. His cock slowly lost its hardness and sadly slipped out of my now freshly seeded man cunt, some of his sperm quickly oozed down my inner thighs, he rubbed it down my leg whilst nibbling my ear lobe, a quick thankyou and he was gone. I quickly finished showering and did my best to remove any traces of sperm from me. How embarrassing if it leaked out whilst I was on the table, why I was worried would prove unfounded as Amy and Lee were about to give me a massage I wouldn't forget.

Now dried off , Amy came to collect me to take me to the room where Lee was waiting, my hair still damp and a complete mess! I tried not to stare at her breasts as they bounced slightly as she walked me down the corridor. ‘ here’ she said to me , opening the door Lee was waiting, ‘ where have you been’ he said ‘ with a knowing smile, ‘we thought you'd got lost’ they knew full well  I'd just been fucked, but part of an act?  Maybe? Or was this  Pauline's doing.

Ok so I might sound a total slut here but I really enjoyed that and although I wasn't sure what was going to happen next I was to thoroughly enjoy it!  however my thoughts drifted off to what Pauline might be up to,  a sobering thought to be honest laced with a hint of jealousy but tonight I was doing what she asked me to do and enjoy myself, 

I was guided onto the table and asked to lie face down on it, a little uncomfortable to be honest as my cock was now super hard, yes the combination of the medication and watching Amy's tits bounce around had done it proud although somewhat painful as I tried to adjust myself to be able to lie down.

The table was adjustable which would prove handy. Lee got to work with the oil's, I was so relaxed I almost drifted off to sleep , yes, lee was very good at this, so good I'd have little to no resistance to any advances he may have been planning.

I didn't have to wait long. Lee got me to turn over, my cock stood straight up like a flag pole. Looks like you could do with some relief he laughed, he wasn't wrong, my cock was close to cumming, I'd only been here 90 minutes and I'd already been fucked once. It was Amy's turn to rub some oil over my body, my eyes closed , she slowly and seductively rubbed the oils into me until the inevitable as her hands went to my balls, then my shaft, I really was now struggling not to shoot my load. Amy knew exactly what she was doing, looking at Lee she told him I was ready. I was helped off the table as she removed her bikini bottom revealing a fully shaved and smooth pussy. ‘ well, let's see what we can do with this ‘ she said as she grabbed my slippery hard cock and led me back to the table. She got on it herself, pulling her legs up to reveal she was more than ready as her moist pussy lips glistened from the fluorescent lights, I honestly thought this was all  Pauline's doing  but later found out she really wanted to have sex with a transexual, I hope I met her expectations?

She ordered me to get on the table with her, her intentions were fairly obvious, I made my way between her legs, a slight hesitation as I hadn't been with a woman for some time now but luckily basic instincts kicked in and my cock easily sank into her warm, wet , slippery pussy. I was shocked how easy it slipped in, I'd momentarily forgotten I'd been oiled up. I gave her a few exploratory thrusts into her, our breasts slipped against each other with the oils that had been rubbed into them, she watched herself with interest and lust as our nipples slid over each other , I thought this was it , I was to fuck her but I'd forgotten about Lee, he hadn't forgotten about me though. I felt the table move slightly as Lee now got onto the table, I was amazed none of us slid off , it  wasn't particularly that wide but Lee managed to get on behind me. The next was inevitable as his cock slipped over my well oiled bottom, he easily found my recently fucked sphincter, ready, he wasted no time as he pushed his 7 inch cock into me, I felt a slight bend in the tip which was rubbing my Insides in all the right places. This was never an easy position to fuck anyone but I gave it my best shot , I slipped effortless into Amy, thanks to the oils as did Lee slip into me. We managed to build a rhythm. I'd push Into Amy then pull out as Lee would shove his cock into me, you could say, and forgive the pun , we were like a well oiled machine! , I think we were all enjoying ourselves with the sounds we were all making, Amy more so as I'd fully penetrate her with my ‘ modest ‘ sized cock then Lee would slam into me pushing his cock as deep as he could into me, pushing me just that little bit further into Amy as I pushed Into to her, perfect teamwork !

Thankfully Amy had her orgasm first , her pussy muscles gripped my cock as her first one swept over her, this was just what I needed to unload what little spunk I had left into her, with Lee still thrusting into me I came into Amy, it was the most wonderful feeling as I attempted to impregnate her, her response was with the walls of her pussy, gripping my cock tightly. She wanted every last drop of my sperm in her. I collapsed on top of her, our breasts now squashed tightly and sideways from our bodies as Lee finished off , using  my elbows I lifted myself off Amy to take the weight off her, Lee wasn't about to disappoint as he cried out , signalling his orgasm , no messing about, in one stroke he pushed as deep and hard into me to release his warm sperm into me,  my willing body greedily accepted it all,  oh  that warm wonderful sensation as he pumped several jets of sperm  into me, the twitching of his glans as they swelled to form a seal which ensured I got all his juices, every jet of sperm into me was accompanied by the warm sensation it made its way deep into my body 

It took him almost a minute to finish  ejaculating into me, a whole wonderful minute! All the time I was still inside Amy, I could feel her pussy muscles still trying to grip my now softening cock. Sadly it had to end as Lee withdrew his cock out of my now sore, pulsating sphincter, doing its best to stop him pulling out, once out, my cock slipped out of Amy. We all got off the table , to be honest I was worried that it wouldn't take , not just all our weight, but our energetic combined love making.

With that, another shower for all of us, after what we'd just done I think we were too tired for any more fun, Ok, Amy did play with my breasts but to her, they were irresistible.

Once done we all dressed and I was to go back to theirs where I'd be picked up by taxi to go home.

I noticed my clothes were missing, I panicked but then saw my ‘ overnight ‘ bag as I called it. Inside was my gypsy dress, white cotton panties and white holdups , not forgetting some sensible shoes.

I sat in the back of the car  going over what had just happened, a quick panic as I worried about what Pauline would think then realised it was her who’d organised this,  I'd enjoyed it immensely. The trip back to their house was quite delightful as Amy and myself carried on where she left off, my dress pulled down to reveal my breasts for her to play with Once again, she now knew what turned me into a slut so quickly and used that knowledge to her advantage, once again I was putty in her hands, my cock once again hard and waiting, but she never gave it any attention, my breasts and nipples is what she wanted and she used that time to her advantage but all too soon we arrived at theirs, much to the disappointment to Amy.

We went in to wait for the booked  taxi , Amy and myself sat on the sofa and she asked many questions about , well me , she was genuinely interested in Christine. Lee was getting a little bored with our ‘ girlie chat’ so offered to make us all a cup of tea, Amy watched as he left the room , putting her finger on my lips , she pulled down the top of my dress to  expose my breasts and straight onto my nipples, yes, she knew exactly what buttons to press, within seconds I was hers, my nipples hardened, as did my cock, I think this is what made me so interesting to her. She sucked away at my nipples like only a woman could, a prisoner to my own Inhibitions, she knew this and lifted my skirt to get hold of my cock, now with a little pre cum on it. Pulling my now pre cum sodden panties to one side she gripped my cock and slowly pulled my foreskin back over my now well lubricated pre cum cock, she liked that as she did that several times to gauge my reaction. In the meantime she was driving me wild teasing my nipples, suddenly she got on her knees and slowly wanked me off, I don't know who was more surprised as she brought me to an orgasm, Amy or myself  as without warning a jet of sperm launched out the end of my cock, straight into her face, I wonder if that's what she wanted but she did look surprised, not to surprised as Lee when he came back in the room with cups of tea. ‘ he sort of giggled saying I can't leave you pair alone for two minutes, Amy looked up at me and we both laughed as my warm  sperm dripped down her face. We didn't really get long to drink our tea as sadly my taxi arrived to  take me home back to Pauline.

Arriving home, Pauline was waiting for me, running to her I embraced her tightly, I mostly, enjoyed my night out, it was Pauline I wanted, Pauline was really taken aback at this, I'd changed, I wasn't that cum hungry slut she first met, I'd become a loyal, loving partner, this pleased Pauline as it confirmed her suspicions about me, from that moment, great things were about to happen to us. We both talked, at great length over our feelings and what we liked about each other, I was really shocked when she recalled our first ever meeting, the dress, my reaction to discovering she was a post op transgender and how, as a lover, how gently I was with her and not like a bull in a china shop, not the best analogy I know but I understood what she meant. Before this moment there was only one other in her life as she thought I wasn't interested in her but her thoughts were always of me and I of her which soon ended that relationship. We must have talked all night as the sun rose over the treeline. ‘ Oh my god, it's your fitting today, she had the train tickets for London , we only had 2 hours to sort ourselves out!

That day just seemed a blur as we made my appointment, the dress was exquisite, Silk, not satin as I was told, it felt so light on me, the dressmaker knew exactly what she was doing, only a minor alteration, I looked beautiful, Pauline watched as a tear of happiness flowed out from the corner of her eye. That done, a quick meal and back home. The thing I think I liked about that day was that nobody gave us a second or judgmental look, Acceptance!.

It didn't seem like five minutes before our, what I thought was a quick trip to the registry office for a civil partnership but Pauline was always the one for surprises. The legal paperwork completed many months previous, my new birth certificate reading my female name , everything was sorted 

It took a while  to get ready but thanks with the help from the ladies from the hotel boutique I was transformed into a princess.  they did an excellent job, mind you I must have gone through half a bottle of champagne in the process! Finally finished and looking at myself in the mirror I tried not to shed a tear so it's not to smudge my makeup a  pip outside the house,  my car had arrived and the chauffeur came to the door to escort me and my two bridesmaids from the boutique to the classic silver Rolls-Royce a bit over the top for the register office I thought that Pauline wanted me to at least arrive in style and she wasn't kidding  we drove past the registry office I tapped on the window behind the driver in a panic telling him he'd gone past, stopping at some traffic lights he turned around to me,  ‘it’s not this one, Pauline's waiting for you around the corner’, the only building i knew around the corner was a large church then it hit me,  then i panicked, driving round there it was , quite a crowd , the church decorated with flowers over an arch. I asked if he could just go round the block, brides prerogative! That must have been the longest two minutes of Pauline's life as I got myself back together, this I wasn't expecting, Pauline was very good at surprises.  We arrived back at the church. The chauffeur came round and opened my door and helped me out along with my two bridesmaids , Pauline was waiting for me at the altar, looking round to witness my arrival, my entrance was, I really wish I could explain how I felt,  never in a million years would have thought I'd be in this position. Looking at the sea of faces, there was one I wished I could see, Ann, my first wife, sadly now gone but I'll always remember her as the woman who made this all possible. 

I walked down the aisle, bridesmaids Each side of me towards Pauline, a tall man I couldn't quite remember waved at me, his partner holding onto his arm, then a familiar face, a grey haired coloured man with a goatee beard , THE JAMAICAN!!, I must have blushed as I recognised him, Pauline had been busy!

I knew I was going  to sign a register, not a marriage register, that was when it hit me just how much she loved me, to be honest once at the front with Pauline it was  all a blur yet again as I was overcome with emotions, thankfully it was recorded, the look on our faces really was true love as we looked into each others eyes ,, the vicar was really good and put me at ease as we went through our wedding vowels. It really was the best day ever! , the evening reception back at the hotel was fantastic, the party went on into the night, the tall man who'd waved at me in the church came up to us, ‘ you don't remember me do you’?  I looked at him but for the life of me couldn't remember, then he just said ‘ you remember that night you stayed at my house’? Nope, still oblivious to who he was, then it hit me , it was my friend who'd I'd ‘ accidentally ‘ inseminated, my first time! Turns out he stayed in London after uni and drifted into the stock market, quite successfully by all accounts. Pauline went over and kissed him on the cheek ‘ so you're the one’  she said, well to be honest, if it wasn't for him I'd have never met Pauline.

The Jamaican came over and congratulated us, I wondered why he was here,  thinking back it was only right he came to the wedding, well he had fucked both my wife's hadn't he!  so a bit of history there, but most of all, we were still friends, even after all this time. The party went on but for us, it had been a long day so with apologies to our guests, we retired to our room and for a joke we put a Do not disturb  on the door handle , that actually proved to be a good idea as there were some shenanigans going on that night! , at one point there was a scream from one of the rooms , I turned to Pauline and said’ looks like the Jamaicans found the bridesmaids , with that we just burst out laughing, 

We really didn't get much sleep that night and by the sounds of it, so didn't some of our guests.

Morning breakfast in the dining room revealed several people with sore  heads, some others with sore bottoms  by the way they were sitting, then there was the Jamaican with BOTH our bridesmaids! NO!! he didn't, I was only joking about the bridesmaids! I looked at Pauline and she looked at me then back to the Jamaican with our bridesmaids. We just couldn't stop giggling, They looked pretty worn out so there really was life in the old dog yet. Thankfully this was a one off, we wanted the hotel and restaurant to be known for all the right reasons 

As predicted, it was a success,  next week we're going to New York to oversee the inauguration of our newest hotel. Yes, our vision had caught the imagination of the Americans. 

Looking back over the last 45 years I've had some good times from when I accidentally inseminated my best friend and he then turned me into his sissy, a turning point for me,  to Peter and his wife who really showed me the ropes, quite literally! and our hotel ventures , then onto Pauline who turned my life around and made me see the real  me and now married. 

Yes I was happy at last, however there was one last shock of a surprise, she never mentioned it and neither did any of her friends but I questioned myself as to how she could afford expensive things , the designer bridesmaid dress for instance that got ruined.

Well, you could have knocked me down with a feather when Pauline finally confessed to me that she was actually a multi-millionairess, a fact she'd not flaunt as she was a down to earth woman , she kept that fact secret from me to make 100% sure I wasn't a ‘gold digger’.  At the end of the day fate brought us together, we were the perfect match! 

Now as a couple we were known for being mischievous at times  but we do like fun and I guess we're going to grow old disgracefully just the way it should be xx 

Well that's it , my story shared with you, I hope you enjoyed my journey from the fumbling young man who accidentally inseminated his best friend to where I am now. Every morning when I wake up, I kiss Pauline and thank her for everything, she knows what I mean. Oh and as for the millionaire bit, yes we do have nice holidays and I haven't changed, I still drive a secondhand car with no expensive tastes., well perhaps my walk-in wardrobe, I'm not saying it's large but perhaps it should have its own postcode, well surely that's a woman's prerogative!  

          Christine x













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Written by Christine63

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