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By (user no longer on site) OP
over a year ago
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I will break this story up into several parts as it will be rather long to tell. It's a story of friendship, love... heartbreak... and lots of sex...
I had been friends with Jim (name changed for this story) for over five years.
We had met in college and I instantly liked him because of his views about everything. - He was not'conditioned' as so many are nowadays. - He was a free-thinker... a free-spirit. - He did his own thing and didn't care if anyone else liked it or not.
...And I... Even more so. And so Jim was drawn to me also. - We 'clicked' very well.
Jim had (for those five or so years) known only the 'male' me.
He knew that I publically crossdressed and was fine with it (in-fact he thought it was great); but he had never seen me as: 'Amy', mostly because he resided about 30 miles away now and I saw him rather infrequently.
One day; (not so long ago), I saw Jim and told him I was thinking of going away for a few days to a particular city for a little break.
"Could I come? - I'd love to get away from it all for a while". He said.
"Sure. But I am going to be crossdressing for all the time I am there". I said.
"That's ok, I don't mind that", Jim assured me.
We decided to book a hotel, but the prices had sky-rocketed that year due to all the nonsense going on in the world; and we decided we would both be 'comfortable' in sharing a room together...
... And a bed.
"Remember I'll be crossdressed!", I told Jim.
"Yeah yeah, I know! I don't do trannies! - You're safe!"
"Ok!" I laughed.
The day of departure came.
Jim had decided to drive us the 80-odd mile to the hotel we were going to be staying at.
"It will be better than fanny-arseing about with buses and trains", he had mumbled one day.
I told him to pick me up in the High Street of my village, as I had to get a few items from one of the shops before leaving.
When I came out of the shop, I saw Jim's car ahead and I smiled at him and walked towards him.
He nodded and turned away.
I tried opening his door and he turned; puzzled.
"Let me in Jim!", I said.
Jim's eyes went wide and he said my male name out loud with a question mark.
"Of course it's me!" I laughed.
Jim opened the door...
Then he sprang to his feet and got out the car...
"H...Hey wait, let me get those for you", he said; coming 'round to my side of the car and helping me with my rucksack, handbag and shopping bag.
"...You're treating me like a lady!" I laughed.
"Oh... Well, yes... I mean... Well you are... Sort of", he stammered.
Jim waited until I was in the car and he closed my door and walked around to his side.
I sat there (as I had done so many times before)... But it felt SOOOOoooo different this time...
Jim climbed into his side.
He looked me up and then down...
..."Shit...." He smiled. He shook his head. - "Fuck me Amy, I wasn't expecting this at all".
"What?" I laughed, turning to him.
He looked at me for a second, right into my eyes; wearing an expression I had never seen on his face before and then he shook his head again with his eyes closed and started the car...
..."You look... 'real'", he said, driving off.
Jim had surprised me with his reaction to me as a 'woman'.
I had had other friends in the past surprise me with their reactions too though.
One friend I had had was a very shy man who had never been with many women, (though in his mid forties).
... When he came to visit me one evening and I let him in (whilst I was dressed as a woman); I found him to be incredibly shy around me. - Just as he was when he was around real women. - It was cute, but also pretty weird at the same time. - I guess his eyes were telling him one thing and his brain another?
"Hey it's just me!" I would say to him.
"Yeah... Yeah I know..." He would stammer, but he could not hide his seeming 'attraction' to me in my female guise.
It surprised me greatly that 'open-minded' Jim (who was a hit with the ladies) was reacting in the same manner. - He wasn't even swearing as he usually fucking did all the fucking time. - He was being very... 'gentlemanly'.
On the way (in the car); we spoke more in-depth about my crossdressing as we had ever done before. - Jim hadn't realised how much of a lifestyle it really was for me.
We also spoke about what we would do during our holiday. - He wanted to know if I'd still do some things with him in male mode (like go to the waterpark).
"I can't", I said, reminding him that I hadn't brought any male clothes with me.
"Ah ok...I just... I don't know how I'd feel walking around with you dressed like a girl everywhere", he said.
"Hey, it's cool, we can work something out"; I assured him.
When we arrived, we ate at our hotel and had a drink.
After the drink; Jim relaxed a bit and felt comfortable enough to explore the city with me in my fem attire.
I think he was surprised how 'easy' it was hanging out with a crossdresser... Nobody cared. - Nobody was staring or making comments.
...We had so much fun! We visited an outside (and inside) tourist-attraction and sat in a cafe and walked around a beautiful park/garden and then went to more shops for a look-around. - It was great... Very pleasant and relaxing... Especially for me in my bare legs, boots and black mini-dress! - The warm air was upon my smooth, soft skin and it (as always); felt amazing.
In the evening we watched a show, had a few drinks at a bar and then retired to our hotel room.
We giggled about the events of the day as we got ready for bed. - We had had a few good laughs.
"Hey, do you sleep fully-dressed a girl?" Jim asked suddenly.
..."Sometimes", I said. (I actually didn't... I thought sleeping with a wig and makeup was too uncomfortable).
"Ok", said Jim.
I didn't ask Jim why he had asked me that question... I got a strong sense that Jim (possibly) WANTED me to remain in complete fem-mode and I decided then and there that I WOULD remain in complete fem-mode...
Jim was a nice guy... And... (Although he was my friend)... He was cute...
I was interested to see what might happen between us... Was that wrong? - I'm not sure... I don't think it was...
Jim (again; VERY gentlemanly), said I could use the bathroom first.
I brushed my teeth and freshened myself up.
I also took off some makeup around the eyes, so that I didn't have too uncomfortable a sleep.
When I came out of the bathroom - Jim went in.
I stood in the room; looking at myself in the mirror... I was wearing nothing but a short, see-through black babydoll dress...
I asked myself a question as I stood looking at myself... A question which demanded an immediate answer, because the cock... Sorry... 'clock' was ticking...
The question was... Would I let my friend Jim 'take' me if he wanted me?
I continued to gaze at myself in the mirror... My long blonde hair... My long slim, smooth legs and slender feminine body...
..."Yes... I would", I whispered in a gasp; realizing there was moistness between my legs.
I climbed into bed, waiting for Jim.
When Jim left the bathroom, he checked his phone for a moment, then he turned off the light and climbed into bed beside me.
"What a day!" He said, laughing... "My future offspring will never believe this one!"
I laughed.
Jim, turned to face me.
..."Don't you ever wish you were a female ALL the time?"
..."Yes", I admitted.
(Long story short... We spoke about 'transitioning' and that sort of thing, and I told him my reasons for NOT transitioning... (Some reasons to do with health, some to do with other things)...
"...I've learned to live like this and be content", I told him...
..."But"; I added... "If I woke up tomorrow - irreversibly a woman... I wouldn't complain".
Jim seemed to be a bit sad at my 'trans-story'... (Of how I'd grown up feeling confused about who I was and all that).
At one point, he let out an:
"Awww!"... And he touched my face softly and caringly with his hand.
...Quickly - he pulled his hand away from my face and he turned around with his back to me...
"Damn!... Another lifetime Amy!" He laughed... "Another lifetime!"
(What he meant by that was that in another life (or some alternate reality) (where I was a real female); he would have slept with me.
...That was all a bit much for me, and I (very annoyingly) showed more of my feelings than I wanted. - I suddenly wept and got out of bed.
I went into the bathroom and Jim shouted after me; asking if I was ok.
"Yes, yes, I just get sad about all this stuff sometimes; it never goes away", I answered.
He was somewhat understanding... But I knew that noone REALLY understands the torment of such feelings unless they have experienced them for themselves.
As I stood in the bathroom, I recalled an incident some years before... A man whom I had really grown fond of (I had 'probably' fallen in love with him)... One day, he had held me out at arms length as he looked at me for the last time... A tear in his eyes (this was his goodbye to me)... He told me:
"If only you were a real female Amy... If only".
"...B...But...I want that too", I cried.
Then he walked away.
...It completely broke my heart... I've never gotten over it. - Some nights I wake up in a cold sweat recalling the moment.
I came out of the bathroom. Jim had turned the light on in the room.
"Are you ok?" Jim asked.
"Yeah."
"No you're not", he said; getting out of bed.
Another tear came into my eyes... Just flooded right out! - And I turned away from Jim and sat on the edge of the bed.
..."Hey... You told me in the car earlier you were happy with both sides of you and that you saw crossdressing nowadays as just a bit of a fun", said Jim; sitting beside me.
..."I am... I do..." I admitted... "I just get a bit confused at times that's all... An old wound got opened... It wasn't your fault".
..."Well... I'm confused too... So don't worry about it", said Jim... Sounding a bit irritated.
..."What do you mean?" I asked.
"Nothing!", He said quickly; brushing it off, and turning off the light... "Come on! - Let's get some sleep!", he said; climbing back to bed.
..."Jim please... What do you mean by you are: 'confused' too?" I asked as I climbed into bed beside him.
"Ahhh never mind Amy", he said, laying down in bed.
..."Ok..."
We both lay still in bed... Both on our backs. I could hear Jim breathing softly... Sweetly.
He turned to me...
..."I don't feel like I'm here with (**** (My male name))", said Jim. - "I feel like I'm here with someone else entirely... I really do feel like I am here with a woman called Amy".
Jim told me he couldn't get his head around the two different sides of me.
..."Hey, don't worry about it... Neither can I", I admitted. "I mean... In male-mode I HATE shopping... Yet in fem mode I love it... In male mode I never go to pubs or clubs - yet you can't keep Amy away from them... It's all very strange... I don't try to work it out anymore".
Jim was smiling as he listened to me speak.
Then He really surprised me... He suddenly got down right down to the 'nitty-gritty'...
"Amy... I'll be honest... I would NEVER date a crossdresser... I couldn't deal with all the shit that would go with that... And I love women and I want to have a family someday and all that... I don't even fancy crossdressers... Generally... But..."
..."But what?" I asked... Rather abruptly, turning my eyes towards him.
Jim leaned up on his side and looked right into my eyes.
"There's something I would love to find out", he said.
"What?" I asked; turning on my side to face him.
"Can I see if this feels as good as I think it will?" He said; his voice becoming a whisper...
Before I could react; Jim was on top of me, pinning me down by my wrists... His tongue halfway down my throat. He winched me silly for ages and kissed me all over my face and down my neck and then he started sucking and biting on my earlobes.
Both of us were extremely 'hot and bothered' and had lost control...
I pulled my wrists free and ran my hands down Jim's back and down into his boxer shorts. My hands were on his hairy arse; squeezing his tight cheeks. I tried to pull his shorts down but couldn't in my position.
Jim stopped kissing me for a second - yanking his shorts off in one fell swoop and throwing them onto the floor, along with the bed covers. He then stared at me for a moment; looking at me like a man-possessed. I looked back at him... My eyes full of lust.
Jim growled deeply like a big cat and then greedily stuck his tongue back into my mouth.
As I sucked on my friend's tongue, I could feel his hard, naked cock pushing against my naked bum as he gyrated himself against me. His cock-tip was wet and I felt damp underneath my smooth ballsacks and down my arse. Jim took hold of his dick and pointed it right to the entrance of my pussy and he began to push slightly...
TO BE CONTINUED... |
