You might be wondering why a sissy is writing about a girl crush but, as our experimentation continued over the following weeks, I learnt a lot from Rebecca, some of which I wouldn’t understand properly until much later.
One day she told me “sometimes I squirt when I touch myself”. We undressed and lay down on her bed, her laying on her back as she began to play with herself, while I lay on my belly between her thighs, watching her fingers caress her gorgeous little pussy. I didn’t need to touch myself to get hard as I watched her fingers sliding between her wet lips, first rubbing at her clit, then sliding down inside her vagina. After a while, as she rubbed herself harder and harder, her thighs started to tremble until, with a quiet moan, she suddenly removed her finger and a little jet of liquid squirted from her pussy and splashed onto her leg. I stuck out my tongue and lapped up the sticky drops, tasting her pussy juices for the first time.
At our next meeting, having thought of nothing else but the taste of her delicious little pussy since, she let me try to make her cum with my tongue. I lay down between her thighs, my nose nuzzling her mound of pubic hair while my tongue slid in between the lips of her delicious, wet pussy and around her clitoris. In a slightly awkward position, Rebecca stretched her arm down underneath her body, reaching up between her buttocks in order to slide a finger into her pussy while I kept my mouth clamped around her lips, determined not to miss a drop of her precious cum when she reached orgasm. It took a few attempts but one day, as her body began to convulse gently with pleasure, I suddenly felt a warm liquid squirting between my lips, as her pussy delivered its precious gift of cum into my eagerly waiting mouth. A delicious gift I swallowed with immense pleasure.
Rebecca was always happy to share the results of her own experiments with me. “Did you try putting things inside you?”, she asked one day, and proceeded to show me how she used her favourite objects to masturbate. I watched, getting hard as usual, as she inserted a deodorant bottle with a rounded cap inside her pussy, but her absolute favourite was a hair brush. The handle was shaped with undulating ridges which gently stretched her pussy as she slid it in and out of her vagina. As I stroked my cock to match her movements, she suddenly pulled out the brush, lifted her knees up even higher and, to my surprise but immense pleasure, she pushed the brush into her cute little asshole and continued masturbating.
After Rebecca came, she asked if I would like to try. I must have looked doubtful but she quickly reassured me that I didn’t have to use the brush. We swapped positions, me laying on my back with knees up and legs spread, while she knelt in-between my thighs, one hand holding my erect cock, the other stroking me between my buttocks. She wet her fingers inside her pussy, then began to gently insert one fingertip into my virgin ass. As her finger slowly pushed inside me, any doubts evaporated and I began to experience an erotic sensation, more intense than anything I had felt before. The palm of her hand pressed against my butt as her finger reached all the way inside me, then she began slowly moving her finger in and out, stroking my cock as she did so, and giggling contentedly as the first dribble of precum spilled onto my belly. I thought I was already experiencing the most intense pleasure possible, when Rebecca tried something different. With her finger all the way inside, she began to wiggle her finger around in my ass, twisting and turning, bending and stretching her finger, as I began to squirm in ecstasy. With her hand wrapped tightly around my cock, and her finger stretching my tight ass, I soon came, ejaculating more intensely than ever before, cum splashing onto my chest and my face, even a few drops spilling into my open mouth as I gasped with newly discovered pleasure. Rebecca looked pleased with the results of her experiment and slowly slid her finger out of my still tingling ass before bending forward to lick the cum from my body.
My first crush at school was a girl called Rebecca. She was considered a swot, and wasn’t the most popular girl in the class, but Rebecca had many redeeming qualities, a least as far as I - a horny teenaged boy - was concerned
Firstly, physically. Most boys thought she was too boyish to be sexy and, to be honest, she was skinny as a rake with a chest as flat as a pancake. She was quite tall for a girl, around the same height as me, with gorgeous skinny legs that started at her slim ankles and ended at her pert little ass. A tiny waist, an almost completely flat chest, a pretty face with small features and a head of light-blonde hair. Her skinny little body drove me nuts with desire.
Secondly, her nerdy side meant that Rebecca was curious about everything - intellectually and, luckily for me, sexually. Things started a couple of days after a sex education class at school, when she rang me to ask how erections work - “Is there a bone that slides in to make it hard, is that why it’s called a boner ?”. I told her it was hard to explain and that she would have to see for herself, and so she told to come over the next day while her parents were at work.
When I arrived, she had obviously spent the night thinking deeply about penises and she bombarded me with questions as though we were revising for a science exam. Not entirely satisfied with my answers, she soon decided that a practical examination would be more enlightening - “Can I see it?”, she asked. Eager to please, I undid my trousers, pulled them down to my ankles with my boxers and sat slightly awkwardly on the sofa. Rebecca knelt in front of me and began to look at me closely, while asking still more questions - “Is it normally that size? Why are the balls so wrinkly?”. Finally, after staring at my penis intently for a few minutes, she uttered the words every teenage boy wants to hear - “Can I touch it?”.
That was the first time somebody else had touched my cock and so she got a very rapid demonstration of how erections form. Her fingertips had barely touched my balls when my soft little penis began to expand and stiffen. By the time she began to gently touch the shaft, now standing up in front of her, I was already rock hard and feeling extremely excited. “What do you do when you play with yourself?”, she asked, and so I showed her how to hold me. Extremely turned on by this time, no sooner had she squeezed me with her hand and begun to stroke me, she was given a demonstration of ejaculation as my cum squirted all over my shirt. Still holding me, she observed with interest as my cock let out another squirt of cum and my cock started to lose its stiffness. Seemingly content with the demonstration, she sent my heart racing as she asked “Do you want to see me?”.
I nodded shyly and Rebecca stood up, unbuttoned her skirt and let it drop to the floor, before sitting down on the sofa. I knelt down, looking at her smooth, skinny white legs stretched out in front of me and, more importantly, at the mound inside her panties which I was about to discover. I reached up hesitantly and took hold of her little white cotton panties, and began to pull them down as she lifted up her bottom and then, as I pulled the panties over her feet, spread her legs so that I could take in the wonderful sight before me. Her short blonde pubic hair was almost transparent, allowing me a view of her beautiful little pussy. The outer labia were almost as pale as her legs while, between them the light-pink edges of her inner labia peeked out. Below I caught a glimpse of the pink rosebud between her buttocks. As I stared at the wonder before me, I felt a tingling in my balls, and a little drop of cum dribbled onto my thighs.
I slid my hand slowly up along her lovely smooth thigh until I felt her pubic hair ticking my fingers. After a moments hesitation I gently stretched out my hand and began to gently touch her pussy lips, feeling the different textures of skin under my fingers. After a few minutes of exploration, Rebecca reached down and guided my fingers to the more interesting destinations, moving my fingertip in little circles around her clitoris, then sliding it down between her wet labia until my finger was at the entrance to her vagina. As she slid my finger inside her warm, wet pussy, the incredible sensation was too much for me and, with a shiver, my cock started squirting cum as Rebecca giggled with pleasure.
A contented sigh from above me seemed to suggest that he was enjoying my efforts. While I continued to stroke him and explore his cock with my tongue, I felt his hand on my body again. This time it slid down across my belly, moving gently over my hard cock, pausing briefly to cup my balls, then moving slowly further down. I bent my knees and opened my thighs, forming a perfect sissy diamond, as his hand moved across the smooth skin between my thighs until his fingertips found my boy pussy and began tentatively exploring the area. Suddenly his hand disappeared, only to return moments later, wet with his saliva. His fingertip began to push more insistently at my hole, wiggling gently until first the tip slid inside, followed by the first knuckle then, with a delicious feeling, the second.
The sensations coming from between my buttocks were making it hard to concentrate on sucking him but apparently I wasn’t the only one with other things on my mind. I felt his finger slide out of my ass and he leant back, his cock sliding out of my mouth as he stood up. For a moment I was shocked, devastated at the idea that the incredible sensations that had been turning me on so much were already over, but he leant forward, took my hands and pulled me to my feet. Still holding my hands, he guided me towards a large, cylindrical hay bale not far away. He placed my hand on the top of the bale, then stepped back behind me, as I placed my feet slightly apart and leant forward. I felt his finger slide inside me again, then a rush of feelings as he wrapped one arm around my waist and gripped me tightly by the hip so that I could barely move. His finger disappeared and was replaced by a new sensation as the tip of his cock began rubbing impatiently against my ass. I closed my eyes, took a deep breath and, as I breathed out and relaxed, felt my little hole suddenly open as the tip of his cock began pushing in, spreading my ass until - as I let out a moan of intense pleasure - the head was inside me. He began to slide slowly in and out, easing a little more of the shaft inside each time.
He let go of my waist and placed his hands on my shoulders, pulling my body down onto his cock to help him penetrate me more deeply. It wasn’t long before I felt his stomach rubbing against my bottom as he pushed against me. As his thrusts became more regular and more intense, I could feel my cock bouncing back and forward between my thighs and, soon after, a wet sensation as the first drops of precum spilled onto my legs. The pleasure was so intense I could barely stand, and I leant further forward, wrapping my body across the curve of the hay bale with my bottom facing up towards him. His hands took firm hold of my hips as he thrust inside me, his breathing increasing in intensity. A tingling sensation began in my legs, then moved up through my thighs, reaching my groin and intensifying until, with a long moan, the cum came spilling out of my cock, splashing down my legs and onto the ground. Perhaps spurred on by my orgasm, he pressed down on my body more firmly, and began to thrust much faster, pounding my ass against the hay bale until his breathing was punctuated by moans. Suddenly he wrapped both arms around my waist, pulling my body against his with all his strength as he pushed his cock up and inside me until I was on the tips of my toes, almost lifted off my feet by the force of his penetration as, with a moan that was almost a shout and a shiver that went through his body, he came inside me, holding me tightly against him as I felt his pulsating cock stretching my asshole as he pumped his cum into my ass.
As the vibrations in our bodies subsided, he relaxed his grip around me and I flopped weakly forward against the hay bale, all the tension and strength in my body disappearing at once. As I lay there, I could feel his cock still inside me, but the intensity of its throbbing was fading. I felt his body begin to move away from me, a new sensation began building up in my body as it relaxed. I concentrated on the feelings of his cock sliding slowly out of me - both deliciously pleasurable and unbearably sad - and, at the moment when the tip was finally pushed out by my hole closing tightly again, a stream of pee came rushing out of my cock.
I remained leaning against the hay bale, recovering from the physical sensations and not daring to move, or turn my head to look at him, all the while wondering if he would say anything. Soon though I heard the rustle of fabric, the sound of a zip closing and, after a moment’s silence, footsteps receding across the field. I stood and watched him walk away, the sun glinting on the beads of sweat on his back, as I felt his cum slowly dripping down my thighs. I lay back down on the grass where he had found me, closed my eyes and began to daydream about what would happen if somebody caught me naked in this field.
I love the summer. As soon as the weather is warm enough, there is nothing this sissy likes more than to get naked outdoors.
This week has been lovely and hot so, one afternoon, I found a spot in the middle of a freshly-mown field. I wasn’t trying to get a suntan, I just love the sensation of slipping out of my clothes outdoors, laying down and feeling the soft grass underneath me and the sun on my skin. And, I admit, the risk of being caught adds to the fun - part of me is terrified I’ll be caught, while the other secretly hopes I will be.
As I lay there, looking up at the blue sky, the sensations of the grass and flowers gently tickling my skin were enough to turn me on, my cock stiffening in the warm sun when, suddenly, I heard a whistling noise in the distance. Starting to panic, I looked around but the sloping field, which made it the perfect secluded spot, also meant I couldn’t see very far. I wondered whether to risk standing up to throw on my dress but, before I could do so, a head appeared over the ridge only a few hundred metres away. Rapidly the figure of a young man came into view, whistling as he strolled down across the field towards the next village.
His current course across the field would take him within a few dozen metres of me but, as I lay in the grass not daring to move, something seemed to catch his eye. At first he seemed to carry on walking straight ahead but, as he looked in my direction, he gradually turned and began walking towards me. Too scared to move, and too late to hide, I hoped against hope that, somehow, it wasn’t me he had seen, and that he would pass by without noticing the naked sissy laying in the middle of the field. Closing in fast by now, he had, of course seen me and finally stopped to stand just a metre or so away, saying nothing, but casting his curious gaze over me from head to toe.
Stripped to the waist, wearing only shorts and work boots and carrying a backpack, he was probably one of the local farmhands. Despite my panic, I managed to notice that his body was tanned and well toned - muscular from the farm work, but not excessively. While admiring the lines of his arms and thighs, I wondered what to do - should I try to explain ? What would he do ? How would he react ?
After few moments of silence as we looked at each other, he spoke, asking simply “Sissy?”, as if the flowery summer dress, and pink panties laying on the grass next to me weren’t enough to be sure. I nodded nervously, still unsure of his reaction. He continued calmly looking down at my naked body, as though trying to reach a decision then, nodding his head and beginning to smile, he took a step forward and bent down on one knee beside me.
He reached out and, before I could react, slid his fingers across my belly and scooped my cock, soft again after the panic, into his hand. Gripping me firmly and staring at my cock, I let out a little gasp of relief and pleasure as he began gently squeezing me and, after only a few moments, his massaging had made me hard again. Seemingly pleased with the result, he lay my erection down on my belly and turned his attention back to me, shifting his stance so that he was now on both knees level with my shoulder.
It didn’t take this sissy long to decide what to do next. I reached up and undid the button of his shorts, then opened the zip. I sat up and ran my hands around his waist, feeling his warm skin under my fingers, then moved them down across his firm buttocks, pulling his shorts and boxers down with them, then lay back down on the grass to admire the view. I couldn’t help noticing that his tan extended inside his shorts and all over his nice dark cock. He smiled down at me as I slid a hand up along his thigh, until I felt his pubic hair brushing against my fingers. Looking up, I could see his already firm cock curving down towards me and, leaning forwards, I moved my head up to bring him closer to my mouth. First, a tentative kiss on the very tip of his cock then, after feeling the warmth and weight of him on my lips, I began to plant kisses all over, moving slowly down the shaft until my nose is buried in the manly odour of his pubic hair and my lips were on his balls. Then I began to use my tongue, lapping at his balls, then making long wet strokes up along the shaft of his now even stiffer cock until I found myself back at the tip, my tongue making circles around it while I gently pulled his foreskin back with my hand. The head revealed, there was no way I could resist spreading my lips around his now fully erect cock, sucking him into my mouth.
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