Henry

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At last it was nearly time and after a shower and shave I headed out.

As I neared Henry's house I didn't feel that confident then remembered I had consumed a tidy amount of Scotch before our first encounter and at this point was stone cold sober. Walking up to the side of his house I unlatched the gate, turning to shut it I slid the security bolt just to be sure we couldn't be interrupted.

I raised my hand to knock then remembered he had said to just come in, turning the knob I entered the house quietly closing the door behind me.

The house was silent apart from the ticking of an antique timepiece in the hallway, my heart rate was currently at twice the speed.

The curtains were drawn through the house and my eyes were taking time to adjust to the gloom. "Henry, are you in here?" I whispered.

I heard a creak on the stair and turned to see Henry slowly descending wearing a Kimono type robe his legs clad in white silk.

"Hi" he whispered standing before me. "Hi" came my weak reply.

He slowly pulled the cord from the robe and looking me in the eyes slid the flimsy garment off onto the floor behind him.

I gasped as my gaze started at his feet up his stockinged legs, lingering over the white sheer panties encasing his semi erect cock, matching garter belt and then a white bra. I was instantly aroused not because I found him feminine, his sprinkling of grey chest hair was still visible between the cups of the bra, but it was how the lingerie perfectly suited his slight frame. The stockings accentuated his long slender legs and the garter belt his slim waist.

"Turn around" I whispered, he did his best at a graceful twirl and my arousal ramped up as his perfect bubble of a bum presented itself to me, the white panties covering half of his cheeks the remaining fabric disappearing into the cleft between.

"Do you like me like this?"

"No" I said, his face fell and his hands covered his face, his lip trembled and it looked as though he was going to cry.

"I absolutely love it" I whispered in his ear as I wrapped my arms around him pushing my erection against him.

"Really" he whimpered as I ran a trail of kisses across his shoulder and my hand touched the outline of his engorged cock.

"Take me to bed and fuck me please" he panted.

"No Henry, I'll take you to bed and make love to you."

He climbed the stairs and I followed mesmerised at the sight of his plump buttocks perfectly framed within the delicate white lace fabric, my cock needed a release and I knew exactly where it needed to be.

Once in his bedroom he turned to face me and taking both my hands we kissed.

While we slowly made out Henry kept thanking me for understanding his secret fetish and how it had taken a lot courage to finally show himself as he truly wanted.

I told him he looked sexy or maybe slutty and he liked that.

He unbuttoned my shirt kissing each nipple as they came into view, then my trousers and kicked them away and soon stood hard and naked before him.

I sat on the bed and pulled him by the hips toward me, my lips kissed his cock head through the sheer fabric then pulled down his knickers to allow his erect shaft some space. I hadn't really considered sucking a guys cock before but this felt right, I didn't want any old cock, just Henry's.

His helmet brushed my lips and I smelt the musk of another man, I tenderly licked his slit then opened my mouth and engulfed his swollen member. Although he was rock hard his glans felt soft in my mouth, as I began to accept more of his manhood into my mouth Henry had placed both hands on my shoulders for support, his whole body seemed to be trembling and he was trying to say something.

"No one.......never had.......oooooh fuck yes" words escaped his mouth incoherently and I suddenly realised what he was telling me, this was a first for him as well, in that case I thought better redouble my efforts.

He pulled me off him and crawled up the bed, discarding the panties he beckoned me to him, I lay beside my new male lover but he turned and with a wicked grin lay on me facing away. His cock swayed above my eager mouth and as I took him in again I felt his wet warm mouth on my swollen cock head.

Sparks flew in my brain, sucking while being sucked felt so bloody good but little did I know that the best was yet to come. Reaching around his stockinged legs I managed enough leverage to get my head under those sweet cheeks, kissing one then the other I stretched them apart and smelt his sex, it drove me wild seeking out his hole I ran my tongue up the cleft I wantonly licked and probed as he writhed with pleasure. I couldn't really say how long we pleasured each other in this position but I felt my balls tighten and knew I didn't want to finish just yet.

Henry and I lay facing each other tasting each other's sex as we kissed, reaching over he handed me a small plastic bottle, "I think its time" he whispered. "Henry are you sure about this, I don't want to hurt you, we can cum another way if" he put his finger to my lips to shush me, "I'm ready as I'll ever be, I want this, I want you inside me taking my virginity."

He got on all fours and pushed his pretty arse upward, kneeling behind him I squeezed out a decent amount of the clear gel between his cheeks then liberally coated my steel hard cock. I ran my finger around his opening and felt him stiffen as my middle digit probed and then entered him, another finger joined in and soon I reckoned he was ready.

Holding my cock I lined it up with his muscle and pushed slightly against him, Henry moaned as I felt his channel resisting my entry then threw his head back as my flared helmet entered him. I held it there for a while asking him if he was ok, he nodded so I pushed a little more watching, mouth opened and panting as two inches was now inside his warm rectum. Slowly but surely inch by inch I was in him up to the hilt, my pubic bush touched his skin, I draped myself over his back, "Henry I'm in, you still ok?" Fuck.....yes.....but you feel so big."

I withdrew slowly until the ridge of my glans came into view the slowly pushed my full length back into his tight man pussy.

And fuck was he tight, without sounding rude to members of the opposite sex that had last been in my bed, they were of a certain age and had plenty of experience in that department, I hadn't felt anything this good since my teenage years.

The feeling was exquisite as I watched my cock start to piston in and out, I stopped for a minute fully inside him as he clenched his love muscle around my shaft, fuck this felt so dirty, so wrong but I didn't care nor did it seem to Henry as he started to verbalise our love making.

"Yes....yes...fuck me harder" he moaned as I quickened the pace, "fuck me with your big cock, fuck me like a woman", this was a side I certainly hadn't seen from Henry but his dirty talk was pushing me over the edge.

The room smelled of sex and the sound of my flesh slapping on his filled my ears, any concern about his wellbeing was long gone as I drove my cock into him nearer and nearer to completion. I felt my balls tighten and in a frenzy reached around desperately seeking his hard cock, finding it I gripped him tightly and began to wank him as my climax built. "Henry.......I'm.......fuck......CUMMING" I shouted as my balls shrivelled and unloaded deep inside him.

I had to take a moment to regain my composure, both our bodies were sweaty from the sex and I realised that Henry had cum over my hand and the sheets beneath him.

I rolled off and we both lay beside each other panting but smiling.

I came too sometime later, it was dark outside and realised we both had nodded off, I quietly made my way to his shower to clean up, the spray felt invigorating and looking down saw that I was once again fully erect. The door opened and Henry entered, he kissed my back and began a sensual cleansing job on my cock and balls.

We fucked twice more that evening and early morning, he rode me wearing a black babydoll and then I did him missionary while he wore the red knickers, both times we both climaxed together.

We regularly meet, sometimes two or three times each week for slow and sensual sex, but always on a Sunday, our special day.

The End.

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Lovetobebi99Lovetobebi994 months ago

As a married guy in the uk who loves to wear panties, this is just the ultimate fantasy. What I wouldn’t give to be you or Henry or even better with you and Henry - a dream cum true, so so hot xxx

Farmer61Farmer615 months ago

I love the story, the cross dressing is so great!! Would love to cross dress with someone older! I'm 62

AnonymousAnonymous5 months ago

A beautiful story of love and lust, very exciting!

AnonymousAnonymous6 months ago

First class story I never had the chance to meet someone to make me a sissy I just an old married man wishing this would happen to me. Please lets have the part 2&3 even

AnonymousAnonymous7 months ago

I like it when older guys enjoy something, I’m 76

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