Learning to Please

By Chuck Hughes

Published on Feb 14, 2011

Transgender

Learning to Please - Part 14

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.

"...I think by now Jack will be ready to mount this sweet little ass of yours - are you ready honey?"

"Yes, I...James...I know that Jack is your man, but I am really ready to...to get laid and...I want to see him soo bad now" I was afraid that he'd be upset, me choosing Jack instead of him, but he seemed to understand.

He reached back and opened the bathroom door, holding a hand out gesturing me to go first.

I took a deep breath and walked past James and into the bedroom. I immediately noticed Jack, propped up on pillows in the center of the bed, nude, hands folded confidently behind his head, looking at me. My stocking feet glided across the hardwood floor and I wished I had a nice pair of heels on to add a strut to my walk, to show a little confidence of my own. But it would have been pretend - I actually felt nervous as I approached the bed. The bedcover and blankets had been removed and set onto the dresser, folded. The lighting in the room had been dimmed, most of the light coming from the black lacquer and glass storage headboard unit. I stopped and stood at the foot of the bed, looking at Jack, my heart in my throat. He was beautiful, masculine. He raised a knee and casually threw a hand onto it, striking an artlike pose which, perfectly, gave me a view of his beautiful cock laying between his legs. In it's semi soft state I could see it was already a thick 8 inches, with the head peaking out from the foreskin.

His bright blue eyes stared at me - he was silent, cocky, knowing that my knees were shaking as I stood before him. I couldn't bear the silence, I needed to get some sort of reaction from him, so I asked "Do I look as ridiculous in this outfit as I feel?" meaning every word of it.

He smiled and I melted "Baby, you look perfect - hot, sexy...turn around so I can see that ass of yours again". I slowly turned as requested. I was now facing James who stood leaning on the doorway to the bedroom, his eyes lingering on both of us. He caught my eyes and gave a motion of his head to indicate that i should turn back to Jack, which I did. Jack looked at me as he reached down and held his cock, giving it a provocative shake saying "I've seen enough Chris honey, why don't you come up here so I can give this to you?"

I crawled up the middle of the bed toward him, slow and catlike. I straddled his body and placed my hands on his shoulders, expecting him to lay back. Instead he sat there and threw an arm around me, pulling me in for a kiss. We were kissing wildly as he guided me to sit next to him, his hands running under the lingerie top and grabbing my breasts. I withered and fell onto my back, him now atop of me, kissing me, touching, squeezing, probing me everywhere. With one hand I felt down and took hold of his cock. It was now fully aroused and pulsing in my hand with small thrusts from his hips. Over his shoulder I saw James approach with a glass jar, a fishbowl, in his arms and he reached in and grabbed a handfuls of candy - in all sorts of colorful wrappers and tossed them freely on the bed, laughing and saying something I couldn't hear. As they landed on the bed I noticed that they weren't candy, they were condoms, all different styles and brands.

Jack had a hand under my thong and was working a finger into my bottom. I felt the bed shift and noticed James crawling over to us, gently rubbing Jacks back as they both looked down at me, serious and lustful. My heart was racing and I know they saw lust in my eyes too - a different type of lust, a receptive lust - I wanted them to take me, use me. I felt so naked, so needy. I reached my hand up and gently stroked James' face. He closed his hazel eyes as if thinking, remembering something from long ago.

We spent the next several hours in a haze of lust, mostly remembered as vignettes - some of tender moments, others of dominance and submission, others of control and mild abuse:

...being introduced to Jack's cock at eye level, learning how to touch and move the foreskin, with my fingers and with my lips

...tasting Jack's cum, the sweet paste-like taste and tasting James' which seemed to have a soapy after-taste

...sucking James as Jack fucked me from behind and them switching positions before Jack came, Jack ripping his condom off before putting his cock into my mouth

...James holding my head as I knelt before Jack, Jack forcing his cock deeper and deeper into my throat, me gagging as they working us together and apart as I'd gag, the bile in my mouth, gasping for air, James with a hand on my forehead, the other holding my lower jaw open as Jack forced his cock deep and finally pumped his seed down my throat, James harshly telling me to breath through my nose

...laying between the two of them on my back, them taking turns slipping their cocks into me

...Jack taking me standing up as I leaned against the wall

...James standing at the edge of the bed fucking me doggy style

...Jack pounding into me with long, strenuous thrusts as I laid on my stomach with a pillow under me, his collapsing as he came, yelling, and then exhausted, James on his knees, waiting to get inside me but letting us enjoy the moment

...James straddling my chest, force feeding his cock into my mouth, erupting his cum and milking it onto my mouth and face

...Jack fucking me as I laid on my back, face to face, like a woman, and after he came, leaning over the side, instructing me to remove his condom and to lick the head clean

...James squeezing one of my nuts tightly as Jack alternated between spanking me and slam fucking me

...Jack watching and encouraging me as I gave James a warm, slow, tender blowjob, James playing with his nipples as he shot his cum into my mouth

...Jack laying on his back and me laying on him kissing, him quickly bear hugging my torso and raising his knees, trapping me against him, exposing my bottom as Jack squeezed in and fucked me roughly

Afterwards we lay exhausted. They were both physically spent, each had cum in me and on me several times. Used condoms and wrappers littered the bed. My body was sore from all the odd exercise, my bottom was sore too, but I felt happy. There was no doubt that they both used me like a fuckdoll, but I felt good about it. I liked it. I liked them & I liked serving them like this.

They didn't show any remorse either - they joked and laughed about everything we had done, how they wished they could do more, but were too exhausted. Jack grabbed the phone and ordered a pizza delivery.

We laid there tangled in each other resting. James asked how long I had been gay and I told him my brief, sordid experience with Howard. They seemed most surprised by my description of Howard - physically extremely different from them. When the pizza arrived we ate in the living room continuing our discussion of all things sexual. They discussed different ways of meeting guys in the city and gave a few suggestions to try, ways to meet guys for quick hookups and advice on bad things to look out for. They had now taken the role of mentor or older brother and I was glad for the information and chance to ask questions. They opened my eyes to a whole new world with a whole different vocabulary: twinks, trolls, trannys and so on.

I took the risk of asking them about the outfit I was wearing...where did it come from? James explained that one Saturday night a few months ago they picked up a girl at a bar and brought her back to the apartment. As they walked past an adult video store she asked them to buy her something sexy wear, which is where the baby doll top and pink thong came from. James modestly added they they had some wild sex.

I commented that she must have been pretty small to fit the outfit and Jack added that she said she was 20 but probably was still in high school. James quickly added that she was no virgin - she knew what she was doing.

"Well, that's not entirely true James" said Jack and they both laughed a little.

"What's that mean?"

Jack filled me in. "Well, you see, this particular beauty was quite at ease and very free with certain sex acts...you know the oral and the vaginal kind? Well, by now you know that our friend Jack there has a proclivity for the fanny. This poor dear was quite alarmed at one point to find herself in an awkward position - that is face down and bottom up - and experiencing the unusual sensation of pressure against her 'back door'. She tried to cry and talk her way out of it, but Jack...well you know Jack."

With shock I asked Jack "You raped her?"

He leaned forward, serious now "No, I didn't...when she was done talking I simply told her what I wanted to do, what I needed. She nodded her head yes and I continued".

"So, she let you have her ass?"

Jack nodded casually and James added "The poor dear cried the whole time too, but she didn't say 'No' or 'Stop', we're generally pretty careful about that sort of thing, especially with the younger ones."

"Thoughtful of you" I added, but also finding myself to be aroused by this tale...her willful submission seemed very familiar to what I went through with Howard.

"Yes, she did seem disappointed that I also took advantage of her 'bottom embrace' when Jack was through. And of course, when I was done Jack had another go at her, the poor thing. So, if you'd like to keep the outfit, your welcome to it - I don't think she'll be coming back for it." And they laughed.

I suggested that maybe they could keep it here for me. They stopped laughing and shared a few nervous, knowing glances. Jack finished his beer and walked his plate into the kitchen. As he left the kitchen he walked to the bedroom saying he was going to take a shower and that we should talk.

"Talk about what?" I asked.

"Well Chris," James started, "perhaps you didn't know, but" he was choosing his words very carefully, "we want you to know that you are a nice guy - a great 'girlfriend' if you will - and we both had a lot of fun with you today, but..."

"But what?" I croaked.

"Dear, this isn't going to be a recurring party for us, I'm sorry Chris."

My face burned with embarrassment. The fifth wheel. What a dork I am. Did I think these two guys really wanted to be friends with me?

"I see that your upset Chris, but, well you're young, you'll understand this when you're older, but Jack and I are in a committed relationship to each other. We don't cheat, but occasionally we invite someone into our bed that we both share. Just for fun, a one time thing."

"Just..for..fun" I dumbly echoed.

"A one time thing," he echoed back, "I'm sorry dear...I know..." he said with compassion.

My face was still burning and I wanted to get up and run out the door. Jack was going to take a shower, was I supposed to chit-chat for the next 20 minutes so I could say 'goodbye' politely? I couldn't hold it together that long, I had to get out of there.

"So, um, I understand, it's cool, gosh I'm such a fool...but you guys were cool...I guess I should get dressed..." I awkwardly got up and brought my plate and bottle into the kitchen. James watched me with sadness in his eyes as I crossed into the bedroom. I got dressed quickly, realizing that I didn't want to see Jack, afraid that I'd cry. I left the negligee and stockings - I could stand to look at them.

I walked back to the living room. James was leaning against the wall with his arms wrapped around himself, looking mortified. We locked eyes and I knew he knew the pain I was feeling, I knew that he felt it before himself many times. In that moment I found some sympathy for James and some relief for myself - he was worried that his lover might be more interested in me, or that I might try to work my way between them. My leaving would lift a burden from his shoulders.

"I guess I should be leaving now"

"Yes, let's get another look at you in your new coat"

As I put the overcoat on he, once again, stood in front of me and roughly pulled the lapels and slapped my shoulders. His eyes were red and rimmed with tears as he said "It does look great on you". My eyes were now clouding with tears and I knew I couldn't say anything without erupting in a sob. I simply nodded and tried to smile. I held my hand out for a hand shake and he took it, pulling me in for a hug. As I squeezed myself against his shoulder my tears fell on him. After a moment we parted and composed ourselves, he wiped away a few tears of his own.

Feeling the need to say something, to not simply leave in silence, I took a deep breath and said, "I, I'm new to all this, and I've got a lot to learn, about life, and relationships, and," the words caught in my throat, "and I don't know everything but I know enough to say 'thank you' and I'll remember you, both of you, please tell that to Jack too".

I turned to the door as he was now crying openly. I was halfway down the hallway when I heard the door open behind me an James call out "Chris, in your coat pocket, I left you a note, which might help...".

I turned back and waved and started down the stairs.

As I climbed the stairs down I pulled a cream colored envelop from my coat pocket, it had my name on it and it was sealed shut. I didn't want to read it then so I stuffed it deep into my pocket for another time, and left the building.

End Part 14


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