Learning to Please

By Chuck Hughes

Published on Jan 27, 2010

Transgender

This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further.

Opening the door slowly and quietly I peered out - searching for sight or sound of Howard. I heard the TV playing in the living room - it sounded like football, so I tentatively stood in the doorway.. I looked down at my long legs and was very aroused at thinking how hot I would look to a horny man like Howard. My freshly shaved legs sheathed in the fishnet bodysuit, the sexy gold high heel shoes, the black slip worn like a mini dress, the lipstick, the bow in my hair, my freshly showered & scented body. I also had a flash of panic - realizing that whatever I thought was going to happen, didn't matter. In a moment I was going to be in front of Howard and he would control what took place. It was a little frightening, but liberating at the same time - once I walked down the hall it would all be up to him.

I had one last minute thought which was that, if given the choice, I should look to give Howard a blowjob or handjob quickly to relieve him of the two weeks of buildup he was holding onto. A distant part of my brain had decided that I didn't want Howard to ruin my pretty outfit by rubbing off and shooting his cum on me. A more immediate part of me rationalized that if he was going to fuck me, it should be after he blew his first load; I didn't want him tearing into me with too much of a frenzy!

I took my first step out into the hall and carefully started walking toward the sound of the TV. I was taking very slow, deliberate steps to keep my balance, which had the effect of my walking very quietly. As I reached the end of the hallway I politely knocked on the wall as he noticed me, looking up from the reclining chair. "Hi, mind if I join you?" I asked in a soft voice, smiling at him. Terror gripped my throat, wondering how he'd react to me.

He shared a beautiful smile which immediately put my fears to rest - standing politely and holding out a hand "Wellllll, oh wow, you look beautiful. Come hear and let me see you". He turned off the game and stood there in his bathrobe, holding his arms open, beckoning me. I was blushing deeply as I walked, trying to effect a feminine swing to my hips. Howard's eyes were big as saucers as he looked me up and down. His cock was already at half mast starting to poke through his bathrobe.

As I approached he took my hands gently in his and held me off to admire me up close. "Oh baby, you look wonderful - better than my wildest dreams", he gasped.

"Thank you...and thank you for all the shopping and the planning, everything was just perfect for me...which really helped, ...it was, you know, very nice of you".

I started to feel a little self conscious as he stood there staring, ogling, over me, so I nervously said "Well - can I have a hug and a kiss now?"

He regained composure and pulled me in against him. I practically tripped in the heels, but he caught me and a strong embrace. One hand deftly snuck under the slip to rest on the exposed flesh at the small of my back, pulling me against him. The other hand immediately gripping an ass cheek. My arms went around his neck and I tilted my head and offered my lips to him. We kissed deeply, passionately, as our hands roamed about each other.

As I kissed him I brought one palm to his shoulder to gently push back to make a little space between us; keeping eye contact I trailed my hand also his torso, smoothing my way down to the opening in his bathrobe. As I took gently hold of the thickening shaft I whispered "I know you're horny baby, but I've been dreaming about this part too...".

Slowly stroking the shaft I kissed him. He grabbed my wrist firmly, smiled wickedly and said "Let me tell you what I need you to do right now, OK?"

I nodded 'yes' as he continued.

"I want you to walk -in those nice high heel shoes - slowly, over to the couch and bring back a pillow". As I walked he coached me to place my toes as I walked to get the right wiggle. I bent over in a slow exaggeration to lift a large end cushion from the couch, hoping it gave him a view up under my slip. Turning I walked slowly back to him, maintaining eye contact. As I approached he started to spread his legs, opening the bathrobe up completely and tucking most of it behind him, placing his hands on his hips, just under the mass of his belly - fully exposing his chest, belly, cock and legs. "Get down on that pillow and kneel before me you hot little bitch" he said with a stern tone, which sent a shiver through me.

I dropped the pillow at his feet and kneeled close to him, my face clearly right in front of his cock which was now fully erect and bobbing straight out, straining. Not knowing if he wanted to order me through this, or if he wanted me just to start sucking I decided to slowly move in rather than wait there dumbly. I brought my hands up and laid them softly on his thighs as I moved my face straight into his groin, deep into his fur at the base of his shaft. He was freshly showered but I felt his body heat and smelled his musk coming from him. I closed my eyes and breathed it in, and breathed out warm air on him as I rubbed my lips, nose and face right into his body. Keeping my hands gently on the front of his thighs I tilted my head down to place my tongue on his nut sack. I lapped and softly sucked his sack, taking one large nut, then switching to the other, into my mouth for a warm bath.

Small hairs were loose in my mouth and I immediately knew I couldn't ruin the moment with a hairball hacking scene, so I carefully continued as I brought one hand over to take hold of the shaft and the other to discretely pluck the loose hair from my mouth as I continued lapping.

Bringing my face around I started to run my cheek and lips along the shaft, kissing the shaft, as the other hand massaged and tickled his sack. I heard Howard groan sighs of pleasure and was at once happy and proud and pleased that I was bringing some pleasure to this nice man. I looked up to see him but couldn't see his face as I was hidden under his girth.

I purposely hadn't touched the head of his cock yet, wanting to build up to that. Breathing, licking, and kissing my way along the shaft allowed me to gauge the true size of Howard's cock. He was clearly thicker than the banana I had used earlier to loosen my bottom with, but not much bigger than the cucumbers I had been practicing with during the week.

I felt him step back half a step and push my head away. I was now able to look up into his eyes and saw pleasure and lust contort his features, and was worried that I wasn't doing a good job.

"That mouth of yours is sooo hot baby" he whispered, his had gently smoothing my hair. I noticed his other hand held his cock and was squeezing as clear fluid started to leak out. "Open wide baby - time to taste me".

I immediately lifted chin and opened my mouth wide, laying my tongue out as he milked his precum into my upper lip and tongue. I closed my eyes and relaxed tasting and lapping gently with the tip of my tongue. The clear fluid had a slight salty, sticky taste which I savored and then opened my eyes to look up at him and smile, gently rolling his nuts in my hand.

"Nice...good girl, taste it, yeah - that's just the beginning - to coat your throat for me" he teased.

Stepping back he helped me to stand and brought me in for a deep full body squeeze. I nuzzled against him enjoying his cologne and the faint smell of fresh sweat that was starting to rise. He maneuvered us over to the love-seat, where he swung a leg up onto the couch and laid back, fully exposing himself to me. Folding his hands behind his head he closed his eyes and said "Come finish what you started and don't stop until you've taken my full load baby".

I dropped to my knees by the love-seat, maneuvering around for best access, which was me leaning against his belly, looking down at his cock. I licked my lips and worked up some saliva in my mouth. Placing my two hands around his shaft I lowered my mouth over the thick full head of his cock. Not knowing how to do this, I tried to focus on the mechanics - keeping jaw open and my teeth clear, keeping my lips wet and tongue active. I quickly learned that I was not able to deep throat so I focused on using my hands to work his shaft and caress his nuts, while my mouth worked on the head.

He moaned with pleasure and whispered advise. At one point he started bucking his hips and I tried to push them back to keep from have his cock drilled down my throat. But the more I pushed the stronger he thrust & I realized he was enjoying this. I felt the palm of his hand grab my head and push my face down on his cock. Holding my top hand close to the head on his shaft I was able to control the depth of the plunge, my lips were limited to a few inches of intense thrusting which I kept wet and tight.

His breathing was getting heavy, wheezy, and I knew he was getting ready to cum. He shifted position, rolling toward me, now standing over me as I laid back against the couch where he had been. In the moment I caught my breath he had thrown his knee onto the armrest and was now straddling my face, holding my head telling my "Open, ...take it, ...taste it, ...my seed for you baby, take my nut".

I was utterly trapped under him and focusing on the bobby cock invading my mouth. One of his hands came around to take hold of his shaft with me. Now, having me trapped, holding my head with one hand and feeding me his cock with the other it was clear that we was ready to cum and he wanted to make sure that it landed in my mouth where it belonged.

Hoping I could trust him not to gag me I relaxed my mouth, opened wide and looked up into his eyes with love. I was now stroking his shaft with him and rubbing his ballsack, willing him to give me his load. With a grunt he unloaded and started pumping his thick cum into my mouth. I felt it hit the roof of my mouth, my upper lip, I closed my eyes as he milked another thick stream into my mouth, and another, and another. Reclining there, I rolled it around my mouth, enjoying the thick earthy taste. I opened my eyes to look up at him and smile. He was catching his breath, his chest was heaving and moist with sweat, and he squeezed a final ooze of cum out of his shaft and laid it one my tongue.

He smiled down "You are so hot...that felt so good...I needed your mouth baby" he said as I licked the cum from my upper lip.

I smiled and started rubbing his legs and ass from underneath him "Thank you Howard...I...never did...did that before...and I liked it".

"OK, you drained me good baby" he said as he sat down on the floor, rolling back to lay down and catch his breath. Looking at his large body laying there panting, satiated, I was filled with a new desire of my own. I crawled over, moved the pillow under his head so he'd be comfortable and nuzzled against him, my face against the matted hair of his chest. Smelling him, hearing his heart race, feeling his chest move. It was very arousing for me as I laid my body along the length of his. A strong arm was holding me against him.

We laid that way for a long while as he slumbered.

After a while he rubbed my back and I looked up into his eyes. "Did you like that as much as I did?" he asked.

"I loved it, thank you" was my reply.

"Good, but you're not done yet - you need to clean me up" he said, and with a slight motion I knew he had spread his legs. "Use that hot mouth of yours like a good woman".

I sat up and crawled back down to see his flaccid cock laying against his thigh. Residual cum had leaked from it along his thigh and some was up on his belly, matted in hair. Knowing what was expected of me, I gently leaned in and started with a tongue bath - using the full width of my tongue to give him the contact and warmth so he'd know I was taking this seriously. When I was done, I knew his cock head might still be sensitive, so I carefully took hold of the softening shaft and placed the whole head in my mouth giving it a very gentle, moist suck.

As I crawled back I asked "Is there anything else I can do for you honey" in my sweet voice.

He stroked my faced, "You are so hot, I mean you really look awesome, when I first saw you it was like a fantasy from Penthouse".

I blushed and smiled a 'thank you'.

"This ribbon in your hair is a very nice touch, by the way"

"Well thank you, I thought you were too busy with my mouth to notice!" I laughed.

"No, I like the whole package you little vixen...and if I'm not mistaken I noticed that your legs look particularly smooth today" he said as his hand traced along the length of my body.

"Yes, you bought such a wonderful outfit for me", I explained "that I thought you'd like to see my legs freshly shaven".

I brought my face close to his and smoothed his hair back. I wanted to kiss him, but realised that after lapping up cum he might not want that, so instead I laid a slow, pouty kiss on his cheek and whispered "Thank you Howard - for everything...and I'm sorry if I was a tease".

He rolled over to give me a hug and kissed me on the lips. "It's OK if you tease me, as long as you take care of my needs like you did today baby".

We held each other, and probably could have drifted off to sleep, but I sensed an opportunity to talk.

As I pressed against him, I stretched to kiss his ear gently - whispering "...and I know your relaxing right now, but when you're ready I have a surprise for you...".

"Oh - what would that be?" he said, now becoming quite alert.

I nervously bit my lower lip, I hadn't quite formed the right witty lines...I grinned somewhat awkwardly, looking him in the eye and said "Well, last time we spoke on the phone, you were so nice, and...and I was so horny, and ...I started...to have these thoughts...of, you know...like really having sex with you...like a woman...and it was a real turn on for me...and I...you know, I remember you saying that you would want to have sex if I loosened myself up..." I was stammering like a fool and blushing again. How could I be blushing, I had just sucked this man's cock and lapped his cum up like a wanton bitch, and somehow I was still nervous?

"...and, and ... and, well that's what I've been doing all week, you know preparing my ass for you." There, I said it, looking defiantly into his eyes, and then looked away.

His arms gripped me tightly, rolling over and pinning me under him. He looked down with a menacing grin "Oh,that is quite a surprise...you think your ready to get fucked like a prom queen?" he asked as he rolled to free one of my legs, which he brought up and and spread to wrap over him, his hand trailing down my thigh, to my ass...".

Terror must have flared in my eyes as I saw him tearing the panties away and thrusting his cock into me. Instead he patted my bottom gently and said 'Yes, I think you're ready. We should get into a real bed so I can mount you and give my seed to you properly...would you like that?"

"Of course..." immediately regretting my hasty words " I mean I'm hoping that...that we can try it, you know...see if i can take it...".

"That sounds like a 'Yes' to me, unless you're intending to be a little tease about it?" he taunted.

"No, of course not...I really want to try, I mean it...just, you know, I need you to be cool about it, that's all...I mean your cock is kinda huge you know, and you may not have noticed but, you, you thrust like a, like a animal when you get going", I was smiling and blushing, teasing a little now "...a sex crazed, beautiful animal" I added rubbing my hands along his back. "I'm just hoping that you could be gentle enough so I don't get hurt, that's all...".

His cock was growing hard against me "Don't worry baby" he smiled "I'll be good to you - I want you to enjoy it and come back for more...". He rolled over and sat up, pulling me into a seated position next to him. He reached over and lifted the slip off, over my head. He traced his hands down my chest and took hold of my tiny, flat breasts, lightly rolling my nipples with his thumbs. I rolled my head back, relaxing and enjoying his touch. Rising on his knees he came closer and started to nibble my ear, whispering "Now I want to see you get up, and wiggle that hot ass of yours down the hallway to your room, with me trailing behind you, knowing that I love your body and am getting ready to fuck that pear shaped ass of yours".

Now his hands were holding my face and kissing me softly. "Yes dear" was my breathy reply, as I stood, being careful in the high heels.

End Part 4

Next: Chapter 5


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