HRT and Boobs Pt. 03

Despite my reserve my underlying desires were now laid bare, at least in marital confidence. Her HRT continued to feed her appetites and we had regular and quite intense sex. She alluded to buying me a bra; I no longer took this as seriously though, as it felt like our physical relationship was becoming slightly more traditional. She surprised me one evening at bedtime, however, by revealing a Victoria's Secret bag in the bedroom. "Ooh, what's this..?"

The answer was something completely unexpected. Far from being the black items she'd initially suggested, she revealed a tiny, baby pink, sheer embroidered lace half cup bra and matching panties. My heart skipped in disbelief; even when I was dressing fully femme to meet men for sex (something I hadn't done now for over a year), I'd never owned anything as beautiful as these items. She'd caught me off guard though, and I needed a drink. I felt my face burning as I sipped my wine.

She hadn't finished; the set included a suspender belt, and she'd bought nude seamed stockings too. "These aren't holdups, so you'll need to wear them with the suspenders." She watched my reaction intently as she produced each item, asking me what I thought, and how it made me feel. I picked up the flimsy, weightless bra. "It's a 40AA," she told me, adding with a mischievous smile: "If it's not quite right we'll take you and get you measured."

I revealed my erect cock; I had to masturbate right now. "Oh god," I groaned. "Oh fuck, this is so dirty..."

She gripped my balls firmly, kissing me. "Try them on for me baby..."

I pulled on the stockings and she helped me with the little clips on the suspenders, and fastened the bra clasp - the bra was a perfect fit. Even in the subdued light I could see her grinning knowingly. I slid on the panties and she giggled. "There are one or two extra items, too..." She handed me a bigger bag from her wardrobe; it obviously contained a shoe box, which I took out. Underneath was a smaller packet; it contained a blonde wig and a pink lipstick! Is this what you want, I asked thoughtfully, as I opened the shoe box - white patent sandals with a 5" heel. They were trashy and gorgeous.

She touched herself as we kissed. "Total feminised for me. You know you want it too."

"We'll have to be discreet," I told her. "It's so fucking erotic though."

She put the wig on me - it was shoulder length and wavy - and primped it this way and that, cooing with satisfaction. "Pout," she commanded, applying a thick coat of the lipstick. I put on the shoes and fastened the buckles. "Ok," she bustled, "let's have look at you..."

I stood up, pretending to be unstable although I'd long since stopped having any difficulty walking in heels. She purred and started pawing at me, giving my bum a slap. She released my cock from the panties and wanked me insistently, her lips parted and her eyes never leaving mine. My head was spinning with possibilities; I had wanted this for so long but it was still in the back of my mind that she might eventually go off the boil, leaving me frustrated and exposed. This was my lingerie I was wearing now. Would she be happy if I wore it regularly? What about if we were doing something non-kinky? She switched on the TV; any thoughts of non-kinky situations were about to take a back seat, as she typed into the laptop, grinning lasciviously. "You ready for a bit of brainwashing?"

Health warnings appeared on the screen, alluding to the mind-altering nature of the material; I later learned this type of clip had been banned on several of the porn sites because it was too effective. The content started - pink, flashing images overlaid with momentary words - slut, bimbo, sissy, fuck doll. Full on, hardcore sissy feminisation hypno. Gorgeous models strutted on catwalks, blondes in heavy makeup squirmed in groups of muscular black men, countless distended black cocks penetrated pretty blonde mouths and anuses, breathy Barbie-girl voices proclaimed lust for black cocks, makeup and panties. I stood leaning on the chest of drawers, watching the screen, mesmerised. I felt her slide the knickers off me. I stepped out of them and felt her hand between my thighs, urging me to part my legs. Although I didn't want to take my eyes from the screen I looked over my shoulder briefly; she was applying lube to her 9" black dildo. I turned my face back to the screen, my anus dilating as she gently introduced the slippery head.

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She had a work 'thing' at a country hotel a week or so later. There was to be music and dancing, and beautiful gardens and grounds to walk in. We checked into our room and got a bite to eat; chilled for a while til it was time to get ready.

Getting ready included several activities that not many couples would currently have been enjoying. I shaved and moisturised all over and we watched more of the feminisation porn while she fucked me with a strapon, so I'd think about it later and 'remember I was a girl'. To further focus my mind she smoked a cigarette on the balcony, and used her hands on me as I tasted her breath, telling me over and over that she wasn't going to let me cum. By then I was shaking with anticipation about the night ahead.

We had recently enjoyed a clip of a glamorous blonde woman sucking cocks at a glory hole, sitting on a filthy toilet, and I asked her if she would dress like the woman and get made up like her. As I put on my pink bra, stockings, suspenders and knickers, with a dark shirt and linen trousers over, she put on a low-cut, black sleeveless halter neck top and pinstripe trousers. She tied her hair into a high pony tail, and applied the most wonderful smoky eye makeup with heavy mascara and pale pink lipstick, and finished off the look with a diamante choker and earrings. She'd had a french manicure and pedicure, and the whole effect as she put on her block heel sandals was absolutely stunning.

"This is exciting," she said as we left the room. I was very nervous, because anyone putting a hand on my back would be able to feel my bra strap; but she was adamant she wanted me to wear my bra. The sheer stockings and suspender belt felt exquisite when I walked. I briefly felt envious of women being able to wear these items every day, before realising I could wear them regularly from now on if I wanted.

Heads turned as we entered the bar and ordered cocktails; I was so proud of how she looked, her exposed cleavage and her generous boobs quivering as her heels clomped and as we found a table in the garden she added the ultimate accessory to the ensemble by putting a cigarette between her lips, which I lit for her. We circulated and she introduced me to a few of her colleagues; we hadn't discussed it implicitly, but we both knew that I wanted her to flirt. It didn't take very long for me to get my wish; it was just starting to go dark and as I stood at the bar chatting to someone, I glanced over to where to see her giggling with a younger guy, her hand on his arm as she looked up at his face. I couldn't hear the conversation but it was obvious he liked her and appreciated how she looked tonight. I felt a surge of precum escape from my cock.

The night progressed; we were all having fun and getting a little inebriated. We danced, got separated, danced with others. I saw her dancing with two guys, giving them suggestive looks as she wiggled and pouted. What I'd give to see them fuck her at either end, I thought. Then she was with the younger guy again, giggling and flirting, practically biting her lip.

We bumped into each other - she was a bit of a handful so we decided we'd have some fresh air in the garden; finding a bench in the shadows we sat side by side, facing the function room. I asked her if she was having fun. "Mmmm..." she giggled, and threw back her head. She leaned into me, conspiringly. "Are you?"

She took out her Berkeley superkings and lit one. She put her hand on my thigh and her eyes widened as she felt my suspender strap and stocking top. "Dirty fucking sissy bitch," she hissed.

Her fingers found my erection and she started to slowly slide them up and down. She took a drag and exhaled smoke into my face, making me groan with pleasure. "Shall I tell you what I'm going to do? Oh, I'll rephrase that... I want your permission for something.." She kept slowly stroking me through my pants, and exhaled into my face again. It felt like it would go too far, very soon. I didn't intend to tell her to stop.

"What do you want to ask me?"

"That young guy, Rory... I want to visit his room. I want to suck him off."

I gasped. I knew I was going to cum now. All I could do was murmur assent. "Keep doing that... don't stop."

She continued to stroke, slowly and deliberately exhaling every drag of her cigarette into my face. She paused and said quietly "What if he wants to fuck me?"

I felt, heard my orgasm arriving, the creamy wash of narcotic pleasure engulfing me, triggered by her wanton words as much as the realisation I was about to be cuckolded. "Oh god," I whispered. "That's OK. Let him fuck you..."

I managed to stay quiet as my body jolted, feeling the rhythmic pulsing of my cock and balls sending surge after surge of spunk into my little pink lace panties. I gripped the table, my breathing gradually slowing to normal; she pouted and exhaled her last drag across the table as she stubbed out her cigarette in the ashtray. We both giggled, and I told her I should probably go up the back stairs to our room. "Yes," she agreed. "You've made a bit of a mess in your knickers, haven't you, you naughty girl?" She paused and added "Are you sure you're OK with this?"

I kissed her. With her perfume, and the red wine and cigarettes on her breath she smelled and tasted like a goddess. I couldn't have denied her anything she wanted; especially not sexual fulfilment. "I want it almost as much as you do." She promised me she'd be back before daybreak, and I kissed her and made my way through the shadows to our room, becoming aware of my cum streaming down my inner thigh.

Back in the room and out of my trousers I finally became aware of what was happening, and I was aroused beyond anything I'd experienced, despite my recent orgasm. This hadn't been release or satisfaction for me. I wanted to revel in the situation, to feminise and degrade myself further. I put on my white strappy heels and the blonde wig, and finding all her cosmetics in the bathroom I started to get made up with mascara, eyeshadow and eyeliner, blusher, lipstick and gloss. I painted my nails, even put on some of her jewellery. I went through her wardrobe and tried on some of her blouses and skirts, a sequined top, finally a little velvet cocktail dress. Taking out the dildo I propped up the pillows on the bed and reclined, hitching up the dress around my waist.

I reached for a tube of the complimentary hand cream, smearing a generous handful on the dildo and my anus. "Your wife is upstairs being fucked by a younger man, with your consent," I told myself as the dildo penetrated my anus. It felt every bit as good as I'd hoped it would to be feminised and cuckolded. I fucked myself for half an hour imagining them in every position, imagining him kissing and undressing her. The dildo felt so good that I hoped she would let him fuck her anally. It felt so depraved to even think that but I wanted her to give herself completely. I even found myself hoping she would let him fuck her unprotected; I'd had a vasectomy a few years earlier so she wasn't on the pill. She was perimenopausal but I knew there was still a slight pregnancy risk, which made me wank myself harder as I impaled myself on the dildo.

Eventually I took off the dress and makeup, and put on her satin camisole to sleep in. I slept fitfully and woke up to the sound of the door lock releasing as she returned at around 5am.