Team Player - Chapter 12

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We kissed and cuddled in bed for what felt like hours. I couldn’t believe just how exciting I was finding exploring James’s muscular body. A body that I had seen in sports changing rooms, and ignored, many times before.

I wanted to stay here in this moment forever. With my man, treating me like his girl.

My mind wandered to think whether this was how I expected the night to go. It wasn’t. It wasn’t even close. I had expected us to be much more cautious; I had expected the night to end with either a kiss on the cheek and promises that we’d have another date, or a shared realisation that we were probably making a big mistake.

Once the nerves that I had experienced earlier in the night had passed, and there was almost incredibly no awkwardness between James and me whatsoever, all I had wanted was for James to scoop me up, and passionately kiss me. I had been dizzy with excitement, since that first kiss.

“Isn’t this uncomfortable?” asked James, in a hushed tone, directly into my ear.

He was spooning me. Slowly stroking my belly with the hand of the arm that I was laying on, one of his legs carefully draped over me, kissing my neck and nibbling at me. It felt amazing; I was in heaven. It was his free arm that he was referring to. After stroking down my arm and leg, it had worked its way up my inner thigh, and was now cupping my pantied crotch; his large middle finger stroking against where my cock was tucked.

“It is right now,” I said breathlessly.

“Do you not want to let it out?” he asked, “It’d be impolite not to say hello”, he joked

We both giggled.

“You can say hello some other time. I am going to get into my pyjamas though. Back in a minute,” as I turned to kiss James, before sliding out of the bed.

“Pyjamas?” James asked, confused

“I hope you like them,” as I went into the bathroom, to change, and take care of myself. I did not want James to see me after it had been in a tuck for several hours, nor did I want it sticking out the front of my pyjamas. After how excited I had been, it did not take me long.

“You okay in there?” James asked from the bed.

I stepped out of the en-suite, lighting up James’s face, in the dimly-lit room.

“Sam? Will you ever stop amazing me? You are the most beautiful woman that I have ever seen.”

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I knelt on the edge of the bed. “Do you like them then?” I asked, tilting my head.

James shifted under the sheets, his involuntary reaction telling me that he approved. In almost comic fashion, his cock had created an enormous tent in the bed sheets.

We both laughed. “Do I like them? What do you think?” he asked, looking away from me, towards the risen sheets in front of him.

“Well,” I said, “If you think I’m taking care of that again,” crawling towards James, “You’re mistaken!” as I turned away from James, and carefully flicked the tip of his cock, with a giggle.

“Oww!” feigned James. “You owe it to me now!” as he laughed.

“So?” I said, changing the subject from me pleasuring him again, “More beautiful than your fantasy girls from the telly? Who were they, again? Courtney, Plastique and Farrah?” I teased, as I snuggled back up to James, him under the sheets and me on top.

“Ha!” he said. “Well remembered. And, yes. Without a doubt,” in what was an ever so slightly more serious tone. “Don’t get me wrong, I think they’re all very pretty. They’re just TV characters though. You, Sam, you’re amazing. So gorgeous, I can hardly believe it.”

We kissed, as he rubbed his hands over my silk pyjamas and onto my skin. Moaning his pleasure.

“You’re so feminine, Sam. So pretty. So sexy. I am almost struggling to think of you as anything other than a girl, right now.” James went on

I could feel myself going red. “Hmm? I could show you something that could be a nasty surprise.”

James shook his head, and smiled. He slowly moved his hand from one of my bum cheeks, stroking it across my upper thigh, to the front of my pyjama shorts, gently cupping my cock and balls in his large hand, through the silken material. Without a word being said, he took one of my hands and placed it around his still vertical cock. “Does that seem any less excited to be with you?” he asked, as smiled, and gave me a quick kiss.

“To be honest, I’m struggling too, James. My mind has been blown over the past few hours. You treating me so gently, I’m feeling so feminine. I want…” I paused.

James lifted himself up, so he was sat upright in the bed, the sheets covering his lower half, his large, muscular upper body leaning against the headboard.

“What? What is it, Sam? You can tell me anything,” urged James.

“I want; I want to be your girlfriend. I don’t want this to end.” I got out

James looked confused, “Erm, I kind of assumed that didn’t need saying. Isn’t that where we already are?”

“Yes, James. But, it’s more complicated than that. But you’ll probably say I’m worrying about silly stuff”. I added

“No, I promise I won’t. What is it though? What’s the problem? James was trying to reassure, but was clearly still a bit confused.

“I want to be your girlfriend all of the time,” I paused. “It’s back to what you said I was worrying about, when I wondered about what happens on Monday, when we’re back at school. I don’t want to be your effeminate boyfriend.” James nodded his sympathetic understanding.

I went on, “Even if the schools rules allowed me to go dressed as a girl, and even with my own ‘Reacher’ as a body guard,” teasing James with a wink,” I’m neither brave nor silly enough to do that. I’ve not worn boy clothes or used my boy voice since Wednesday. I don’t want to, either.”

“Oh, I see.” James said, with genuine concern in his voice. “What does this mean then?”

I looked James squarely in the eyes. He sat himself up straight, and swallowed hard.

“I don’t know. I think it just means I need to have a chat with my Mum, about what options I have.”

“And us?” James asked, with concern. “Are you dumping me?”

“What?” I cried out, “ Hell, no!” I reassured, with a broad smile.

I saw the tension release from James, as he leant forwards, taking me in his arms for a hug.

“Fucking hell! Don’t do that to me, Babe!” he pleaded

I laughed. “I’m sorry! I thought you were following me.”

James laughed, “Women!”

“Ha! I said, "That’s one thing that hasn’t changed. I’m still a man. You’re beautiful girlie-man. I don’t think like some crazy woman!”

“Yeah, maybe that’s why I love you so much.” James said

“Hmm? I said, teasingly, “You’re just saying that to try to trick me into taking care of ‘that’, again!” I gestured to James’s still engorged cock, and laughed.

“Ah, you rumbled me,” said James sheepishly.

I wasn’t comfortable saying that I loved someone, after having only had romantic feelings towards them for a few days, using James’s joke as a get out, to not share how I really felt. I was crazy about this guy.

“You’ll have to take care of that yourself,” I teased.

“Okay,” said James, climbing on top of the sheets, onto his knees, grabbing his cock.

“Woah! No you don’t, mister!” I chided

James laughed, “I was only teasing.”

I turned off the lights. “Let’s get some sleep,” I said. James just mumbled his agreement, taking up his position as the big spoon. James’s still hard cock poking my bum as we cuddled and kissed each other to sleep.

I woke early, again. Last night’s memories all suddenly flowing back to me, forcing a wide smile. I looked to see James, still deep asleep on the pillow next to me. He looked so peaceful. My handsome man, my boyfriend, as I became excited at the thought.

I then, with the early morning light, saw last night’s makeup smeared across my pillow. “I must look like a complete state,” I thought. I carefully exited myself from the bed, and made for the en-suite, being sure not to wake James. I didn’t look as frightful as I had expected, so after brushing my teeth I quickly made myself look a bit more presentable.

As I walked back into the bedroom in my pyjamas and now tied-back hair, I realised that I must have woken James. “There’s my gorgeous girlfriend. I wondered where you were” he mumbled, still half-asleep, as I made my way back to the bed. “You’re pleased to see me too,” he joked, at my own small tent in my silk shorts.

I got back into bed, and snuggled up to James. “Mmm, I groaned at the pleasure of feeling his warm body.” I wasn’t the only one that had woken up excited. I turned my back towards him, pulling his arm over me like a blanket, and again having his cock stick in my back.

I half tilted my head off the pillow, towards James behind me. He sensed my movement and raised his head to kiss me, pulling me closer into his body. The kissing became more passionate, until the feelings overwhelmed me, and I paused, “James, I want you inside me,” I whispered,

“What?” he asked.

“There’s something you can use as lube over there’” I added, he had heard what he had thought.

“Are you sure? Are you ready?” James whispered, fully waking up quite quickly. I moaned my confirmation.

James jumped out of the bed, as if had just been bitten by a rat. Returning with the cream I thought he could use as a lube, and a condom he’d quickly extracted from his wallet that lay on the floor with all his clothes.

Still lying on my side, he started kissing my neck. Steadying himself with one arm on the bed, he slowly lowered my shorts down my legs, until I was able to kick them off one of my toes. He grabbed my leg whilst I was returning it to the bed, lowering it, and gently turning me over, so that I was lying face down. James encouraged me forwards, so that my upper body was resting on the pillows and my knees; my belly and crotch raised off the bed.

I felt James insert his fingers into my backside, shocking me with how cold the cream was that he was applying. He took a hold of my left hip, and reached his right arm forwards, taking hold of my still erect cock. Again, I jumped with surprise.

“Are you sure you want this?” whispered James

I turned my head as far around towards James as I could, and nodded, “Yes,” I whispered back, “I want you.”

I could feel James steadying himself, before I sensed both a pressure in my bum and a tightening around my cock. The combined sensation was like nothing I have ever experienced before, and acted to take my breath away. Whilst the stroking motion against my cock started to feel more familiar, the discomfort in my anus was entirely alien to me. James continued to press further, pushing himself further into me, causing me to yelp in deep breaths.

“Am I hurting you?” asked James, tenderly.

“No,” I replied, clearly in discomfort. James slowed down his progress.

I had taken almost all that I could take, and was about to ask James to stop, when he withdrew. He then returned, and started rhythmically fucking me in the arse. It was an entirely different sensation. Just as much discomfort from feeling him fill me up, but a different, excited sensation overrode that, until it became pleasant, shortly before starting to feel incredible.

I stopped wincing, and starting groaning with enjoyment. Pushing my elbows deeper into the pillows, so I had more leverage to push back against James, as he thrust into me.

I surprised myself with my own scream, when I came onto James’s hand and onto the bed sheets. James released my cock, taking a firm grip of my right hip, in doing so smearing my cum over my skin.

I then sensed another sensation. I could feel James’s cock start to spasm, as he started to groan louder. Until he let out one cry, collapsing to his right, taking me with him, his cock still in my arse. Both of us panting, and unable to speak.

James recovered more quickly, after he had exited himself from me, and we both lay on our backs; me laying in my own cum and James’s that was seeping out of my backside. I felt high.

“That was,” James paused for breath, “incredible”.

“Yeah,” I agreed, still gasping for breath, “I’ve never felt anything like that.”

“Sam, you’re incredible,” said James, rolling over to face me.

“You did all the work!” I joked, and James laughed.

Taking my face in his hands for a kiss, “I love you, Sam.”

“I love you, too.”

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Comments

Definitely

joannebarbarella's picture

On the other team now!

Thanks...

... for the comment. Do you think so?

Good, she was allowed to ake

Good, she was allowed to take things and her own pace and consent was asked and was given.
He gave her a reach around so he was thinking of her pleasure too.
I do not understand where James' cum came from if he was wearing a condom.
Next time there would be less clean up both wore condoms. they need to get a proper lube.
She might want to get a set of butt plugs.
If she is leaking she might want to use a panty liner or sanitary pad or she could use a tampon.
if she wants to be his girlfriend then a visit to a doctor will be needed and counselling and hormones.
With her wide hip and narrow waist, the may already have a level of female hormones. So even the low dose in the birth control pill might start breast growth in her. She might try her sister's birth control to experience female emotions.
I would have said partner instead of girlfriend this leaves the readers wondering if she is happy with a gay relationship with cross-dressing or will she want to transition to being a woman later.
Her big choice is she a feminine looking crossdresser or is she, trans.

Thanks...

... for your comment. Sam indeed has lots more big choices.

Wow! Didn’t expect that to happen…..

D. Eden's picture

So quickly, but it was perfect!

Yep - say goodbye to Sam and hello to Samantha full time.

D. Eden

Dum Vivimus, Vivamus

Steamy AND sweet

Nyssa's picture

Still smile the whole time I read a chapter of this story. Sam is sprinting towards some pretty major changes, but it feels like she's admitting things to herself as much as it is becoming something. I do worry a little that some of what she's doing is to please James, but it's been sweet so far and she seems happy with where this is taking her. It never hurts to be cherished and desired, does it?

Thanks...

... for your comment. Glad you’re enjoying it. I hope your worries are unfounded.

Change of mind?

Jamie Lee's picture

At one point, Sam said he didn't want to be a girl. And now he wants to be James' girlfriend. He doesn't want to go back wearing boy clothing, he wants to dress as he's been doing.

Does this mean he wants to be a girl, or just continue wearing the clothing? After being intimate with James, will Sam want more of the same or makes changes?

Others have feelings too.

Thanks…

… for the comment. I am sure Sam will find his or her way, with all the support available.