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Let’s get this straight. I’m not gay, not a sissy or faggot, I’m a normal 30ish heterosexual guy okay! So why you might ask am I writing this dressed in a dark blue dress, black stockings with suspender belt, light blue panties with a white polka-dot pattern and bow, matching bra, 3-inch-high-heels, with my cock in a chastity-cage and with my hair, make-up, nails and jewellery all making me seem a quite attractive woman?
Well, it’s hard to believe how I ended up like this. In just 3 short years my life changed completely and all because of one simple moment of madness on my part. One simple mistake was my downfall. Even now when I think about it (which I try not to: but that’s almost impossible), I bury my head in my hands and sob at my stupidity and what it has led to. It’s a bit like how that guy in Tom Wolfe’s Bonfire of the Vanities had his life turned upside down simply because the car he was in took a wrong turn.
My name is — or — was Carl Henley. (Now people know me as Carla Gifford.) Let me fill you in with my backstory.
When I was 19, I was studying law at University. It was there I met my first wife — Amanda – who was studying Design or something similar. We got on really well soon after meeting. She was about my size, sporty (like me) and good fun. We both had concerns about how we were going to pay back our student debt and when I told her that a recent Solicitor who gave a talk at my college mentioned how he was now doing much more conveyancing work for people who were buying derelict properties, re-furbishing them and then selling them on again for a quick and usually handsome profit, I suggested that we should pool our student loans and try and do the same.
Amanda’s dad was a plumber and her brothers and uncles were all in the building trade. Her dad agreed to help us with a bit of cash to add to our kitty and he and the rest of the family agreed to help at “mates’ rates” doing up any property we bought. So, we gave it a go and made a good profit on the first run-down property we bought at auction. We married (rashly I might add on reflection) shortly after. I gave up University as I was just so keen to get my new property development business off the ground. Amanda helped with the design of the furnishing, carpets and lighting etc. and I got to know lots of tradesmen I could rely on.
Soon I had a reasonable portfolio of refurbishments on the go and was mixing with solicitors, mortgage-brokers, bankers and the like. In fact, I played tennis and golf with quite a few of them and was invited with Amanda to plenty of social events. Things seemed to be going well.
Sure, like most marriages, the sex tailed off a bit after a while. We both had opportunities to go astray — and both did occasionally (we were both fit, attractive youngsters after all). But what really finished things was when Amanda said she wanted kids and that having them would make us both more responsible and loving to one another; less likely to be unfaithful.
Now the last thing I wanted was kids! I was working all the hours I could building up a reasonably sized business (another reason I guess why our sex lives went off the boil). It became a sore subject between us; one I avoided bringing up with her if possible. Anyway, she ended up leaving me for some older guy who did want kids and was loaded too.
She “took me to the cleaners” with the divorce settlement and I ended up practically penniless after paying her back her share of the business plus the initial start-up loan her father had made to us plus the not inconsiderable legal fees.
I had to start again from scratch. It wasn’t easy but I made good use of the friends and contacts I’d made in recent years and slowly began to re-establish myself and earned quite a bit of respect in doing so.
Shortly after my divorce, just when I was starting to get things together business wise, I got chatting to Ruth Gifford — the owner of a small but successful marketing company — at a charity dinner. I’d noticed Ruth before at similar events and also at the sports club where we both played tennis and squash. She was my age, slightly smaller and with short, black hair that gave her a sort of pixy-like look. She had a winning smile, bright brown eyes and a trim, well turned-out figure. She too had just been through a painful divorce — her ex was fiddling money from her business to feed his gambling habit — and after that experience, she wasn’t really keen on starting another relationship with a man.
We hit it off though, both acknowledging and laughing about our mistakes with our first spouses and over the next few months gradually turned our friendship into a full-on sexual relationship.
Another good thing about Ruth (although it wasn’t the reason I hooked up with her), was that her father was none other than Max Gifford, who was just about the biggest independent property developer in the county. Where I was buying up and reselling run-down terraced and semi-detached Bostancı Sınırsız Escort houses, he was buying up plots of land and building luxury houses or small shopping malls.
“Big Max” as he was known, had two children, Ruth and her older sister Esther. She too had a failed marriage behind her (her ex was an insurance broker who, after marrying into the Gifford clan, decided to ease up on work and live the life of a boozer). When it became clear to Esther that he was just a lush, she soon booted him out and, from all accounts, much as Amanda did to me, took him for every penny she could in the ensuing divorce.
Esther was a freelance IT and Internet security consultant who worked from home. She was taller than Ruth and had a kind of presence about her. Long wavy auburn hair, a dress size perhaps larger than her sister. She didn’t need lots of make-up to make her attractive to men and I have to admit I had toyed with the thought of trying to chat her up before I’d got to know Ruth — although a couple of my business friends had warned me to steer clear.
“She’d have you for breakfast Carl. No wonder her last husband turned to drink,” one associate who knew the family warned me. I took the advice and never tried it on with her.
She was always immaculately dressed, quite often in trousers that hugged her well-honed buttocks. She wasn’t one for sports so I’d only ever seen her wearing high-heel shoes cupping black nylon-clad feet, one of which had a gold bangle around the ankle — something I found quite erotic. Her breasts were larger than Ruth’s too without being too pendulous. I often glanced at her when she or no one else was looking to admire her nipples pushing through the thin fabric of her bra and blouse.
Max was very protective of his daughters, even more so after they’d made such bad judgements with their first husbands. I know for a fact that once things got serious between me and Ruth, he contacted a few of his friends in the business to see if I was worthy of his daughter. He seemed pleased to hear that I’d resurrected my career after being dragged down following my divorce. I was up-front and honest too about my shortcomings in the failed marriage and how I was a more mature man because of that experience: he seemed pleased that I was so frank and self-critical.
Donna — Max’s wife and mother of his two daughters — was at least 12 years younger than her husband. I only ever saw her when she was in Max’s company and couldn’t say I’d really had a one-on-one conversation with her until after that fateful day when my world came tumbling down. Now in her early fifties, she was clearly a good-looker in her prime and was still capable of turning heads even now. Long, wavy brown hair, curvy and long limbed — she was the tallest of the four Giffords. Max treated her a bit like the male chauvinist he was, talking down to her without realising it when in company. Donna endured it with a knowing, long-suffering smile. Max sometimes referred to his wife’s rather large breasts as “his babies” even when in public. This, Ruth assured me, infuriated her mum, but she bit her tongue and humoured him. Once a male-chauvinist always a male-chauvinist was Donna’s attitude. Sure, her husband had sometimes been unfaithful and they both knew it, but Donna’s reward was to know that whatever jewels or cars or holidays she wanted she’d get. That was the unspoken bargain. She’d put up with his – diminishing with age — sexual advances and who knows, maybe enjoyed it too. But both her daughters confided in me that at times he really pissed her off.
Donna was an active part of the County set; the “ladies who lunch” as they are known. A privileged bunch of spoilt, wealthy women who were kept in luxury by their successful husbands and all lived in big, detached houses well away from the riff-raff. Theirs was a life of health-spas, manicures and pedicures, cruises, designer clothes and jewellery. All had a new car every year (Donna usually chose a top-end sports car more in tune with someone half her age). And for all this, all they had to do was turn a blind eye to their husbands’ affairs and make sure they looked as attractive as their years allowed so as to be seen as a trophy when accompanying husbands to dinners or other social events. Some of them had affairs themselves (Ruth suggested Donna had the occasional fling but she couldn’t be certain).
At the odd barbecue I’d attended at Max’s house, it was hard not to notice when Donna came down to breakfast of a morning in a skimpy t-shirt and without a bra on. Her nipples just had no place to hide and I shot the odd secretive glance in their direction and found myself a little aroused. Ruth’s breasts and nipples were nice, lovely even, but Donna (and Esther too), I reckoned both had larger areolas and more prominent nipples.
Anyway, enough about them for now. Suffice to say that I’d won the approval of Big Max to court and marry his younger daughter Ruth. Ruth Bostancı Suriyeli Escort and I were great in the sack and what made things even more spicy was that Ruth insisted that before we could marry, we both had to be totally honest and up-front about any fetishes or particular sexual fantasies that we had; she insisted on total frankness, insisting that anything admitted now would have to be accepted by the other before the wedding could take place. Now I already knew that Ruth had had the odd occasional lesbian fling and I didn’t mind, it was no problem. In fact, it was kind of a turn-on when we were making love and she’d describe to me her most recent same-sex fling. She never told me who the other women were, only that they were usually with women who were older than her and usually married. Some of these women were, she told me, known to me, but she would never disclose their identities.
I swore to Ruth that I had no “odd” sexual proclivities although I did get extra horny hearing about her lesbian liaisons. I had no gay desires whatsoever or any other fetish. She stressed that it was okay to tell her if I did, she’d understand, she just wanted all this to be out in the open before we committed to marriage. I reassured her again that I was just a normal, straight, heterosexual guy and would only ever worship at the temple of her pussy.
Now married, the event that turned my life upside down happened nearly two years after the wedding. Max had been suffering with his health for some time and probably knew that he hadn’t too long left. He wanted to arrange one last big business deal and get all his family involved so that they could benefit from the future profits and live long and comfortable lives thanks to his acumen and business nous.
It was to be a new shopping-mall and housing development in a nearby town. Max’s company had bought the land and — to many people’s surprise — got planning permission to develop it. He told me I could have a share of the development but would have to find about £1.5million to buy in to it. We both knew that I could get this sort of loan from the banks, they were now eager to help build my expanding business, and with Max’s name behind the project, it would be no problem. It just needed a couple of meetings with a few friends in the banking business and for me to pass a medical for the life-assurance side to the loans, and I’d be a junior partner in the project.
Ruth and I had travelled over to Esther’s house on the outskirts of the town where Max and Donna lived, before going over there to sign the documents that clinched our part in the deal.
We took a taxi with Esther to their parent’s house as we knew we’d all be having a celebratory drink or two after the paperwork was done. We’d arranged to stay over at Esther’s place that night, travelling back home the following (Saturday) evening.
Donna had arranged to drive round to Esther’s on the Saturday morning and take her daughters to a nearby shopping mall where, after a bit of retail indulgence, they planned to have something to eat before going to see an early afternoon showing of some new film at the cinema there. They guessed it would be some time after 4 p.m. before they’d arrive back.
Ruth asked if that was okay, me being alone most of the day and having to fix a meal for myself whilst she went out with Esther and her mum. I assured her it would be fine; I had a few things to do on my laptop and would watch the sport on TV when I’d finished.
We’d both overslept a little that morning, probably due to all the drinks we’d had the evening before. Everyone enjoyed themselves and we all got a little tipsy, except for Esther who’d only had a couple of glasses of wine.
I didn’t bother changing out of the t-shirt and boxers I’d slept in, plenty of time for that later. I enjoyed watching Ruth putting on her make-up and getting dressed after her shower; watching her brush her hair at the dressing table, just clad in a tiny pair of briefs that nestled snuggly in the cheeks of her peachy bottom and hardly covering her bush at the front, little tufts of which peeked over the little bow and lace trim that adorned them. She called me over to help fasten her black bra and could see from my boxer shorts that I was horny and ready for action.
“Not right now big boy,” she smiled and slapped my erection. “I’m running late as it is and anyway, it’d be too noisy. We’d embarrass Esther. Wait until tonight when we’re home, we can make up for lost time then.” We’d not had sex for well over a week – what with me being away on a brief golfing holiday with a few mates and Ruth having just had her period — and although I wanted to have a quick screw there and then, it would be worth the wait. I was ready for action and fully loaded, tonight she’d have me pump my large reservoir of cum deep into her pussy. I could barely wait.
I helped Ruth finish dressing, zipping up her skirt and helping her attach her earrings. Bostancı İranlı Escort She stretched up on tiptoe and held on to my shoulders as she slid her feet into her high-heels, giving me a quick kiss as she did so.
“Calm down tiger. When you next get your hands on this zip, you’ll get your reward.”
Esther was already up and dressed and had made coffee and toast for us, telling us to help ourselves to cereal if we wanted. She asked if we’d had a good night’s sleep and then added that I was to help myself to anything in the kitchen whilst her and Ruth were out with Donna.
Esther was wearing a smart white blouse tucked into the waist of a pair of well-cut, bum-hugging black trousers. I could make out her prominent nipples under her bra if I stared but felt it better not to — just in case I got caught out. (Ruth knew I found her sister attractive -most men did. It didn’t bother her. Esther for her part just naturally assumed all men gazed at her breasts but might not have approved of her brother-in-law doing so, especially in her sister’s presence.) Anyway, once Esther put her jacket on, I put all thoughts of her inviting bosom behind me and set up my PC to start on my mornings’ work. I still felt horny after watching and helping Ruth to dress earlier but was able to hide my stiffy under the dressing-gown I’d put on so as not to cause any embarrassment.
Donna arrived just before nine, tall and elegant in a designer dress — a little black number that would probably have been a bit too young for most women her age – but she managed to carry it off. It ended just above her knee, She, like Ruth was wearing black stockings that finished in a pair of high-heeled black shoes that probably cost an eye-watering amount. Expensive perfume, gold necklace, earrings, bracelets and designer wristwatch completed her stylish look.
“Come on girls, let’s get going. My credit card’s getting itchy,” she joked. And with a quick kiss from Ruth, the three of them left me to my own devices for, well, maybe six or seven hours.
In truth, I didn’t have much work to do on my PC. Sure, I’d check my e-mails and maybe read a few news articles online, it might, take me an hour or two in between making cups of coffee, but after that…?
With time on my hands and the house to myself, like most men, I ended up drifting to the porn sites. It was a daft thing to do of course, I knew I’d end up jerking-off, so frustrated was I at not having come for so long. But I figured maybe it would be better for Ruth if I released a bit of pressure from my pussy-piston before we had sex tonight; that way I’d delay my ejaculation longer when making love to her. So really, I figured, having a wank now was actually for Ruth’s benefit.
This was the beginning of my big mistake. I was still downstairs in my sleeping gear and dressing gown and should have gone back to the bedroom to relieve myself, but Esther’s house was not overlooked and very few people passed by and they couldn’t see in to the house even if they did. Besides, it somehow felt more of a thrill to get my dick out in her front room. No-one would ever know. I had all the time needed to do the deed and spray some air -freshener around afterwards if necessary, then shower and change. So, I spread my dressing-gown out on the floor and propped myself up against the large settee, the PC on the floor nearby ready to be called in to action.
Now, in view of the long, lonely hours ahead, I decided to take my time; no need to rush. Minutes slowly rubbing my cock turned into half-an-hour, then an hour. I wasn’t sure how much longer I could delay completion. I’d looked at the usual sites I visited, “sexy matures” “hairy Asians” but nothing especially fetishist. I’d often watched porn with Ruth, she preferring lesbian porn sites, which was fine by me. Occasionally I’d see a site called something like “cocks in frocks” or “ladyboy love”, you know the sort. I’d always passed them by before but, for some strange reason, curiosity I suppose, I visited just such a site and, well, found it strangely compulsive.
That morning I decided to check out those videos of ladyboy sex, and, to my surprise (and embarrassment) I found myself getting horny at the thought of sex with some of the big-knobbed, shemales clad as they were in the sexiest of lingerie. I found a video, about 40 minutes long, that seemed especially erotic. It was about a western tourist driving in Thailand getting pulled over by the cops for some minor traffic offence. The only way the guy could avoid a heavy fine would be, the arresting cop informed him, to come back with her and her colleague to the police station and pay a smaller penalty.
As you may have guessed, back at the station, in the interview room, the guy is made to strip whereupon the two policewomen strip too, down to their bra, stockings and suspenders, and force the guy onto his knees and make him lick one of the cop’s butts. Meanwhile the other cop reveals a large erection poking through her panties and, when the guy emerges from cleaning the first cop’s butt out with his tongue is, to his abhorrence, ordered to suck the cock that’s now right in front of him. While he’s doing that, the other ladyboy cop has now got her dick out and is readying the poor guy’s bum for penetration.