Family Friend Outing

By Ginna_CD

Original link: https://www.lushstories.com/stories/crossdressing/family-friend-outing.aspx

Tags: passive, anal, cd, crossdresser, fucked

Added: 17 Nov 2012 Views: 15385 Avg Score: 4.9

A family friend fucks me after outing myself to him
A few years ago I went back home to Greece for Easter to see my folks and enjoy a bit of the sun. My folks live in a small town where it’s impossible to get any cock if you are not out. As any typical small town where everyone knows everyone, coming out to a few people becomes coming out to the entire town after a few days. So naturally I spent most of my time gagging for cock in silence.

Every day soon after waking up I would jump in the shower, clean up deep and proper, shave all over and moisturise. When all soft and dry, I’d dress-up in stockings, suspenders and thong, under conventional male clothes, all in hope of getting unexpectedly lucky.

One Wednesday morning, after going through my morning ritual, I joined my folks at the garden for breakfast. They were talking about this old family friend that was visiting with his wife and daughter for a few days and discussing about the sleeping arrangements. At the time I didn’t pay much thought to it. I remembered them vaguely from an earlier visit but I was quite young for them to make an impression on me. And so my day wore on without thinking about them at all. Instead, as usual I was thinking about cock and how to get some.

Lost in my cock hungry thoughts, time went by rather quickly and around four o clock in the afternoon the doorbell rang announcing our guests. Quite docile from the afternoon heat, with a semi erect cock confined in my thong and my mind on much needed cock, I went to get the door.

As I opened the door, I froze in confusion for a minute. In front of me was a rough looking, hairy, tall, beefy guy, in his early 50s, looking rather stern. He wasn’t handsome but he was most definitely sexy, in an animalistic sort of way. My cock automatically responded to the visual stimulus by growing larger and more visible under my tight jeans.

Seeing my hesitation, he introduced himself as Chris and the rest of the family, Lena his wife and Thallia, his daughter. After I mumbled something resembling an introduction as well, I moved aside to let them in. As I guided them towards the balcony where my folks were, I couldn’t help but feel exited by their arrival. When all seated outside I sadly concluded that Chris, even though extremely sexy, was off limits. After a bit I figured I might as well make the most of the situation, hung out with Thallia and hopefully pick up any tips about clothes and beauty products.

The afternoon turned to evening and Thallia and I told everyone we were going out. For the last few hours I realised that her dad was looking at me sort of strangely now and again, almost like he is angry at me. And our statement didn’t make things any better. I could swear he was looking at me completely pissed off but shrugged the whole thing away as my imagination.

My evening with Thallia was a pleasant one. From the moment we met we didn’t stop chatting like best friends and the consumption of alcohol didn’t make things any worse. Once back home, around 11 o clock, the sleeping arrangements were made known to us. The house has only one guest room. And with my old room with two beds, I was expecting for Thallia’s mum and dad to sleep at the guest room and Thalia at my room. To my disappointment they informed us that Christos would be sleeping with me, and Thallia with her mum. Feeling rather disappointed, I said my goodnights, and headed towards my room.

When in the room I decided I couldn’t risk taking my lingerie off in case anyone walked in. I quickly jumped from my jeans to my pyjamas and sat on the bed. Seconds later Christos walked in. He closed the door behind him and approached me with a dark look on his face.

'Listen you little shit, I saw how you were flirting with Thalia,' he said angrily, towering in front of me. 'If you even think of touching my daughter, I’ll beat the crap out of you.'

Seeing him so aggressive and angered, I almost wet myself. My mind was racing, searching for anything I could say that would calm him down. I could see that he was getting angrier by my silence and finally I blurted out the only thing I thought would get me out of this sticky spot safe and sound.

'B....but...I’m...gay,' I stammered meekly.

I said it and sat down tight waiting for a reaction. He just stood there looking down at me. I could tell he didn’t believe me and I started getting worried again about what he might do to me. Then to my surprise, with one movement of his hand, he pushed his shorts down a bit and took his cock out.

He waited for a few seconds and then said carefully, ‘Gay? Show me’.

I was stunned. There it was what I’ve been craving since I saw him, his thick, long uncut cock hanging on top of two big hairy balls. I sat there, my eyes fixed on his prick only a few inches away from my face, trying to figure out what to do. I so desperately wanted to taste it but at the same time was reluctant. I wasn’t sure if he was serious or if he was just testing me to see what I would do. All the worse possible outcomes were racing through my mind but in the end I just couldn’t resist. I reached my hand, grabbed his cock and leaning my head forward I put it in my wet mouth.

To this day, I believe he did not expect me to actually do it, otherwise he would not have offered me his cock. Surprised, he tried to back away but by then I had him already secured in my mouth sucking for all my worth. With my one hand stroking his bushy balls and my other arm hugging his legs I kept moving my head back and forth frantically on his prick. I felt him growing rapidly in my mouth until I could feel his cock head hitting the back of my throat and passing my gag reflex.

With singular concentration and my eyes closed I blocked everything else from my mind apart the cock I was feeding on. Now in its full length, I was exploring the cock head and the foreskin with my tongue. With every entry, his thick veiny shaft brushed my lips making me shiver. And every time I was taking him all in, my nose sank in his thick, curly, coarse bush and my chin pressed on his hairy balls. All the while I never stopped inhaling ecstatically his manly smell. After what seemed to me like ages, he started drip-breeding my throat. His precum, clinging persistently on my larynx started mixing with my saliva giving that always, familiar sense of something thick, slippery and sticky at the same time in the back of my mouth. The whole sensation was enough to bring me back to reality.

Slowing down a bit on the sucking, I opened my eyes and gazed upwards at his face. His expression was unreadable. His eyes were fixed on my head following the back and forth movement.

‘You really like this, don’t you?’ he said observing me how I sucked him off.

I nodded the best I could with my mouth stuffed.

‘Fucking hell, I would never have thought you are into cock!’ he said to himself more than to me. ‘And to think I was worried about Thallia…’ he shifted his head a bit and looked at my pyjamas. ‘You are even getting off on it!’

Hearing that, I became aware that my pyjamas were absolutely soaking with my precum on top of my bulge.

‘Suck my balls,’ he said with a steady voice.

With my eyes still on his face, I removed his big tool from my mouth and started sucking on his balls. His shaft resting on my face would jerk from time to time, betraying his enjoyment and satisfaction. The moment I realised he actually enjoyed all this, an enormous weight fell of my shoulders and for the first time I relaxed completely and started enjoying him.

It all became pure bliss for me. Caressing his big balls inside my mouth cavity with my tongue while inhaling his manhood, I could have been doing it for hours no end. After a while, he backed away removing his drenched nutsack from my mouth. Not wanting to break contact, I reached with my hand, grabbed his solid pole and started stroking it while rubbing his wet cock head on my face.

He watched me in silence spreading precum all over my face.

‘Show me your ass!’ he said abruptly.

And then it kicked-in, I was still in lingerie under my pyjamas. I hesitated trying to decide what to do. I eventually rationalised that seeing me in lingerie won’t make much difference considering I’d been sucking his cock and balls for some time now. And I was way too horny to stop myself.

‘Go on…’ he urged me, mistaking my reluctance for shyness.

I let his pulsating manhood go and stood up turning to face the wall. I took a deep breath and in a single fluid motion I pulled my pyjamas to my ankles and knelt on the bed, revealing stockings, suspenders and thong.

I waited on my knees, brandishing my ass in the air and oddly enough I could feel apprehension and excitement at the same time. At some point I noticed the stretching silence. Chris was totally silent displaying no reaction whatsoever. Eventually I started feeling more and more exposed, wondering whether it was an utter mistake letting him see me in lingerie.

As I was about to get up and get dressed, I felt his hand touching my bum lightly. I froze still as shivers run through my body. I felt his hand stroking my bare ass in circular motions and as in answering a call, my cock started stiffening.

‘Nice ass…’ he murmured to himself, ‘very nice indeed.’

‘And the lingerie?’ he asked me casually making sure he didn’t sound any negative or judgemental, ‘you like dressing up as a girl?’

‘Yes…’ I replied embarrassed.

‘Nice…’ he mumbled to himself and kept stroking my ass

When I realised he liked what he saw, I begun feeling relaxed, horny and confident once more. I lifted my booty higher in the air, reached behind me, grabbed my ass cheeks and spread them wide open revealing my tight hole. The invite to enter couldn’t have been any clearer. Not even if there was a neon sign with an arrow pointing to my ass and the words ‘free entry’ flashing over it! And yet he hesitated.

‘You want me to fuck you?’ he asked uncertain after some time.

‘Yes, please…’ I begged with a voice full of longing.

I saw him from between my spread legs moving away from me. He fumbled for something in his briefcase and came back to stand behind my ass. I heard a ripping noise and saw him throwing on the floor a condom wrapper. He moved my thong to the side and soon after I felt his cockhead touching my asshole. He pushed firmly and steady. Once the head was in I groaned loudly from the pain.

‘Ssshhhh! You need to be quieter,’ he said trying to sooth me. ‘You don’t want your folks coming in the room while you are like that now, do you?’

‘It hurts...’ I mumbled pleadingly.

He stood still for a few seconds, not moving at all. Then he slowly emptied my ass. He pulled my thong from my waist to my knees and then down my legs. The triangular front patch was dripping with my pre-cum. I was mildly surprised when I felt him rubbing the wet thong, on, in and around my asshole, lubing me up using cum.

‘That should do the trick,’ he said mostly to himself. ‘nice and wet!’

He lined up his prick once again against my asshole and started pressing. This time his cock slid a bit easier in. It was still painful but the pain was manageable. He took his time filling my ass with his big fat cock and I was grateful for it. Once in up to the balls he stayed still, waiting for me to adjust.

He grunted when he felt my sphincter relaxing on his shaft and with an abrupt movement started pumping me.

It took longer than usual for the pain to turn to pleasure but when it did it was worth the trouble. He was fucking me hard and fast, ramming his cock deep inside me, and I was loving every second of it. I was moving my ass back and forth, trying to match his movements, slamming it hard against his legs. My groans and moans were getting louder and louder and I grabbed a pillow and pressed my face on it in order to muffle them.

Chris plainly knew how to fuck. With fast movements and powerful thrusts, I could feel his entire prick passing in and out of my sphincter, and with every insertion he was stretching my hole a tiny bit more. Now and again he spanked my ass making my entire hole contract around his shaft and every single time I moaned my ‘thanks’ to him.

After some extensive ploughing he slowed down to a halt and pulled out of me. I was left wondering for a few seconds whether he had finished and I didn’t realise. Soon after and much to my relief, I felt his hands on my ass again. He spread my hole open and spat a couple of times in it.

‘Lift your ass higher, bend your back downwards and drop your head and shoulders all the way down,’ he instructed me.

I did as I was told as he climbed on the bed. He straddled my ass, and in one smooth movement rammed his prick inside me and started riding me with blind determination. It was deep penetration, as I’ve never felt it before. It was all I could do to stifle my moans and groans as he forcefully stretched me.

Not long after, with a little yelp I started shooting thick ropes of cum all over the bed. Spent and dry, my legs started weakening and giving way slowly. And as I was about to collapse, he grabbed me by the waist, fixed my ass still in the air and kept on stuffing my hole relentlessly.

As my body cooled down, my sphincter was protesting with every violation. I buried my face in the pillow to prevent my whimpers escaping and waited for that single moment when the immense pain would stop. That threshold moment I knew from experience must come. As predicted, within a few minutes all pain started fading away and I felt my cock stirring once again. Once again horny I started pushing my ass upwards, meeting his powerful thrusts with an impact.

‘Horny again?’ he asked surprised.

There was no need for a reply to that question, my ass slamming on his crotch was answer enough.

After a while of intense fucking, he took his cock out of my gaping ass as abruptly as he put it in, told me to turn around, ripped his condom off and rammed it in my mouth. It took only three thrusts for him to start squirting. His sperm was free-flowing down my throat and when it had filled it up, started flooding my mouth cavity and dripping down from the corners of my lips.

When he finally finished seeding me, he removed his cock from my mouth and put it back in his shorts. He walked across the room to the bed, lay down and went to sleep without a word.

I got up, turned the light off and returned to my bed. As I lay there, cum drenched, savouring the remnants of his sperm in my mouth and listening to his heavy breathing, I realised that apart from stroking and slapping my ass occasionally, he barely even touched me. That all familiar, sweet and dull ache at my stretched asshole, and the strong, intoxicating smell of his sperm spread all over me were keeping my cock hard and horny. I couldn’t help but feel happy and satisfied. Thinking on my pleasantly unexpected evening and while wondering how the next day will go, I slowly drifted into sleep.

Next morning I woke up feeling rather sticky and excited. I was hoping to get a second round of cock but after looking at Chris’s empty bed I realised I was going to be left craving. I got up, changed the bed sheets and headed for the laundry room and then the shower.

When I joined everyone at the balcony, I both eagerly anticipated and dreaded Chris’s reaction when seeing me. To my disappointment, he dismissed me after a single look. I spent all of that day feeling horny. I was looking for any signs he wanted to fuck me again while making it clear my ass is willing. But he was unimpressed. He didn’t show the least bit of interest.

Night fell and I still was nowhere near sampling that cock again. It was getting quite late and having finally resigned of the prospect, I said goodnight to everyone and went to bed. That night he woke me up by slapping his solid cock on my face. He straddled my face resting his balls on my eyes and proceeded in fucking my throat. He was more assertive than before and wasn’t afraid to touch me. He explored my hole with his fingers and was stroking my face and ass while fucking them. He was more verbal as well. Sometimes sweet, he would praise me for my skills in pleasing him, other times rough, he would order me what to do. All and all, he was more relaxed and I was enjoying him even more. After a long session of pounding all my holes in many positions, he finished by cumming all over my ass.

From then on he didn’t miss a chance to use my holes. From outdoors in remote fields on the outskirts of town, to car parks in his car, he was fucking me like the man he was. He was quite canning and creative at finding excuses to be on his own. Throughout our encounters he made it quite clear that I was there for his pleasure and me getting off on it was a by-product.

Even though we were kissing, he never touched my cock. But it was all fine with me, my holes were getting enough attention for me not to care. He preferred me fully cross-dressed and I was trying to accommodate him as much as possible – always in lingerie, suspenders and stockings and when we were isolated, in heels, skirt, bra, top wig, and make up.

At our sessions, I would not touch my cock at all after his request, not until he was finished with me. Our fucks were so long that I would usually cum just by having my ass pounded. He was calling me his ‘little bitch’ and his ‘little girl’ and I loved it. He even started fondling my ass, whenever he felt like it, always discretely, in public places, even around our families.

It all lasted a week or so and then it was time for them to leave. He did give me his email and we are still in touch, planning to hook up whenever I visit again.