HRT and Boobs Pt. 02

I shouldn't have been acutely embarrassed but nevertheless I awoke in that state. How could I be comfortable crossdressing in private, meeting strangers even, but find it difficult to relax when it became an avenue to explore with my wife? Was it because I'd been burned before, some 10 years earlier, when it looked like that might become an exciting new interest? She had a habit of killing my mood with a bitchy word, a look or a sneer. Was I just protecting myself?

She stretched and turned over to face me. "Mmmm, baby..." her messy hair was over one eye. "You were a naughty boy last night!"

I grinned. "I don't remember..."

"Oh, but you do," she replied. "Something about a bra seemed to trigger you..."

How could I forget? It was going to be difficult to deny how quickly I had ejaculated at the suggestion of me putting on a bra for her, but I wasn't ready to talk about that just yet.

I sat up. "I'll make us a drink." I went down to the kitchen, returning with coffee a few minutes later, to find her sitting up in bed in her satin robe and reading glasses, looking at a magazine which she put down as I handed her the steaming drink.

"You don't have to be embarrassed with me, babe," she told me. "It's just a bit of fun..."

I cringed inwardly. "I know." I tried to keep the tone light, hoping to change the subject, but she was being persistent.

Her eyes were sincere. "I meant it, though. I would like to see you in a bra."

I rolled my eyes and sighed audibly. Damn that HRT! "But you don't want to feminise me... I remember that time when you used to put your knickers on me. God, can't I just have a quiet morning?"

"Sorry..."

We sipped our coffee and our eyes met. we both grinned. She moved closer to me, her heat radiating from her open geisha robe. Her painted nails and yesterday's perfume gave her an air of wantonness, like a courtesan or escort. I liked it, and the taste of red wine and cigarettes on her breath when we kissed. I reached into her robe, touching her belly and boobs, enjoying their fullness and tight cleavage in the position she was in. She stroked me through my thin pyjama shorts, smiling at my erection, and slowly straddled me.

We kissed some more, and she lifted the hem of my tshirt to expose my chest. We paused and regarded each other; her expression was challenging, a half smile with her eyebrows raised. "Well?"

I sighed and lifted my arms so she could remove my top. Her hands slowly cupped me. "You're still oily," she observed, her fingers slowly describing circles around my nipples and her thumbs momentarily stroking them. A cold shiver spread through my whole body. Did I want this?

Her hands continued to circle and define my breasts until she was satisfied that my nipples were fully erect, then concentrating on the larger - left - side, she put her mouth to my nipple, sucking hard and chewing very lightly with her teeth. She cupped and emphasised the boob, giving me uplift from underneath as I had done to her so often.

I touched her own breasts in a similar way, noting her hand was now between her legs. She sucked hard on my nipple and touched herself enthusiastically. "Fucking beautiful titties..."

I blushed, squeezing hers. "Not as beautiful as these..."

"They're going to look amazing in a pretty bra," she replied.

I groaned and rolled my eyes, and she asked me what was up. I thought you liked masculine men, I told her.

"Sometimes..." She saw my eyes and added "I mean, you can wear things for me and still be masculine..." but I'd taken what she'd said implicitly, that a contrast existed between the well-endowed, muscular black men in which she occasionally hinted at showing an interest; and something she now saw in my paler, softer body.

My mind raced that day. Where would this go? She had to go into the office for a couple of hours while I had a few errands. I worried that I would open up to her again just to find her putting me down with a wrinkle of her nose if I went too far. But... As I drove down a country lane a scenario popped into my head, something I'd fantasised about a while ago; in the dream I was wearing a black satin basque, stockings and heels - I was cuffed to a chair in the bedroom, sitting impaled on a dildo while she was on the bed, in front of me, with her legs wide open and a virile young guy on top of her and servicing her enthusiastically. "I want that," I thought, my heart pounding. "I WANT THAT." I said it out loud the second time, and had to pull into a layby. I suddenly had to give attention to my erection, to release it from my pants; to celebrate and admit - if only to myself - my desire to be feminised and cuckolded. I revelled in the exquisite pleasure as I brought myself close to orgasm, holding myself on the edge.

My face burned. I told myself that I had to calm down, to somehow keep my cool and not get ahead of myself. After all, she was probably just thinking of a little bit of bedroom titillation. I had no reason to think that she had suddenly developed urges that would correspond to mine... But I had to see where it would go. It crossed my mind that I couldn't admit that I'd been dressing regularly for some time; it would naturally follow that she would quiz me about what I'd been up to while dressed, and I wasn't sure if I could ever talk to her about that. Also I wanted her to share in the excitement I feel when I put on a bra - I might need an equity card to feign inexperience, but I certainly wouldn't have to pretend to be aroused.

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Neither did I have to wait long. The hints she dropped all afternoon and my aroused state were going to make it difficult for me to stay cool. She ran a bath for us and I opened a bottle of wine. We sipped and chatted. She shaved her legs and handed me the razor with a smile. "Do you mind?" I left the bathroom a short while after she had, shaved and moisturised, to find her at the dressing table. She was painting her nails and I could see her red lace bra and knickers through the gap in her kimono. On the bed she had laid out one of her black lace bras, a pair of black satin french knickers and a pair of sheer holdups! She nodded towards them: "red for me, black for you..."

I took a gulp of the Malbec and sat with my back to her, forcing myself to make small talk as I pulled on the stockings. She replied in a similar way as she applied her lipstick in the mirror. Oh god, imagine this happening regularly, I thought, even becoming second nature. I pulled on the silky shorts and stood up as she approached, smiling. Small talk was over, and she held up the bra. "OK, baby!"

I sighed, taking it from her and pretended to fumble with it. "Here," she tutted. "You've seen me do this enough times... You put it on backwards, fasten at the front and spin it round, then put your arms in. There!" It was a 38D, and tight across my back while being obviously too big in the cup, but she purred with appreciation and kissed me deeply in the subdued light. She'd taken the liberty of connecting her laptop to the TV and a selection of high quality porn was showing. We kneeled together on the bed and kissed. She asked me how I felt.

I was sufficiently emboldened by the wine to answer truthfully, although my face flushed as I tentatively pronounced the words. "A bit funny. Submissive. Feminised." I paused and added 'vulnerable'.

She gently lifted the lace trim on one leg of 'my' knickers and exposed my cock, fully rigid and wet with pre-ejaculate. "but you enjoy the feeling. Do you like being feminised?"

My head swam with arousal. "I think so," I answered, warily. She asked what else I liked.

I had to control what I said, I was still wary of admitting too much. "I like you smoking."

Her eyes widened. "Do you? You like me to wear lipstick when I smoke?"

"Oh yes..."

"What else?"

"I love it when you kiss me and you taste of cigarettes, if you smoked earlier when I wasn't there, and I didn't know you'd been smoking."

She grinned. "Do I taste slutty?"

"A little," I blushed, "but sophisticated, too... Glamorous."

She smiled and gripped my shaft, squeezing hard. "Is that how you think of me?"

I moaned with pleasure and nodded towards the TV. "That's how I think of you."

She turned and looked - a well-built peroxide blonde was on her knees between two impossibly huge cocks, fellating each in turn.

She moved in closer to me; we were now side by side on the bed, propped up on pillows. Our conversation became softer, almost a whisper, and more intense. It felt like we were conspiring, speaking words too sordid to share.

"Would you like to see me do that?"

"Yes."

We kissed. "See me with other men?"

My heart was almost audible. "Mmmm... yeah."

She stroked the bra cups. "Men to fuck me while you're dressed like a tart in girl's panties?"

"Oh god, yes..."

She gave a throaty little laugh. "So fucking dirty... you fantasize about cuckolding."

"Mmmm..." My heart pounded and I felt myself start to shiver.

Her eyes twinkled. "You want to fuck me after they have?"

"Maybe," I whispered. "But I'd want you to deny me... not let me fuck you. I'd have to wank myself off in front of you."

"Mmmm! You want to be cuckolded..."

I knew I was close to orgasm. "Feminised, yeah... cuckolded, denied sex."

She was wet and swollen and obviously close, too. "God, that's so hot." She smiled and stretched to the laptop; as she typed in the search bar I saw the words 'huge cocks cumshots compilation' appear, her browser obviously recognising a search term it had seen before. "Shall we watch this together?"

I murmured assent and stretched out on the pillows. She gently took my hand and placed it down the front of my knickers; it was clear that she wanted me to masturbate while we watched 17 minutes of big cocks spunking. She slid her red lace panties down her smooth thighs and reached for her 8" black dildo. We kissed as she let the head play around the wet opening of her vulva. "What if I told you I preferred my dildo to your cock, because it's much bigger?"

I groaned, slowly stroking myself, precum streaming from me. "I like that. I want to hear you say that."

She gasped as she gently penetrated herself, watching the screen. She whispered into my ear. "I want to suck off big cocks like that, and spread my legs for them. I want them to spunk in me without condoms on."

"I know."

She purred, slowly fucking herself. "It turns me on watching you wanking as you look at those big cocks. You want to suck them, too..."

"Yeah..." It was barely a whisper and I was very close to cumming. She withdrew the dildo and brought it to my mouth. The wonderful smell of her arousal overpowered any thought of resistance I might have had. "Oh god..." I opened my mouth.

"Look at the screen," she told me. "Suck it like a girl would. That's it. Mmm." Her hand was on the back of my head and she slowly slid the shaft in and out of my lips as I sucked and pouted. "Watch that screen. Imagine all that spunk in your mouth."

I couldn't resist another second. I relaxed my clench and slowly pulled back my foreskin, savouring the sublime half-second before an explosive contraction propelled a stream of hot cum three feet into the air, followed by 3 more, soaking my chest, the bra, her hand and the dildo.

To be continued...