First Night Nerves

We kissed longer and longer, our mouths sliding over each other as he kneaded my buttocks. I felt his hand rise and the long zipper on the back of my dress being lowered. His hands slipped inside my dress and his fingers played up and down my spine, then downwards to toy with the back of my g string. His erection was even more obvious to me now. I lowered my arms from his neck and my dress slid easily off my shoulders to fall to the floor around my ankles. My bare skin pressed against his clothes and I could feel the animal heat of his body against mine.

Barry stood back to look at me. He shook his head. "God Tina, you're lovely!" he gasped. I felt a warm glow inside. His fingertips stroked the skin of my shoulders and across my flat stomach. I raised my hands to his waist and deftly unfasten his belt, then unbutton his waistband. His zipper followed quickly and I lowered his trousers to the floor. A huge erection battled to escape from his pants. I eased them over his growing cock and lowered them to the floor. He kicked his shoes away and stepped out of his clothes.

Rising to my feet, I unbuttoned his shirt and slipped it over his shoulders. It fell away, leaving his wonderful body naked in front of me, his erection demanding my immediate attention. My hands lightly touched his firm chest, then the clearly defined muscles of his stomach – evidence of a 6-pack very much present - as I sank to my knees and took his erection in one hand, cupping his testicles in the other. I began to pump my hand steadily up and down, feeling its strength and vitality, before opening my mouth and taking it in. Remembering my experiences in school and Debbie's technique, my tongue lapped over its smooth head and its tip sought out the ridge beneath. I took it further into my mouth and dragged my teeth along its sides. Barry moaned and ran his fingers through my hair. I licked along his ridge, down to his tight sack and back up to the head.

Bending my head and neck down lower, I took each testicle into my mouth in turn, working the shaft with my hand, before sliding a finger in between his buttocks to stroke the rim of his anus. I felt Barry tremble as I worked, and his cock, now back in my mouth, began to pulse. I moved my mouth smoothly up and down his shaft as he swayed back and forth, moaning quietly.

Eventually he must have felt too close to cumming because he suddenly lifted my head away. Taking my two little hands in his big one, he led me to the large bed where he turned me around and sat me on the edge. My stocking-clad feet barely touched the floor. Barry kissed me on the lips and pushed me onto my back.

With consummate skill, he lifted my legs and my g string was whipped away from me, leaving me exposed to his gaze and touch, my pale delicate core framed by the dark silk of my stockings and suspender belt. He bent over and kissed my navel, then his rough tongue licked my lower stomach and my skin coloured panties before his head dipped down and I felt his warm wet tongue between my buttocks. It felt incredibly exciting, but I began to feel anxious inside. I had never been this far with a man before. The tip of Barry's tongue suddenly slid into my anus. Again it felt wonderful but I was more afraid. I wriggled on the bed as Barry forced open my legs and his powerful body rose up over me. I began to tremble.

Barry must have seen the fear in my eyes because he suddenly stopped.

"Is everything alright?" he asked insistently. Then realisation dawned. "Have you ever done this before?"

I shook my head, embarrassed.

"Never?"

Another shake of my head.

"Do you want to?"

My turn to pause. A quick nod and a smile.

"Are you really sure?"

Another nod. Barry suddenly smiled and his body lost its tension.

"Well my love we will have to take it very easy. We'll try it another, easier way." His mouth touched my ear as he whispered "Roll over. Get on all fours."

I did as he said. I felt vulnerable but excited. Barry's soft, warm voice was reassuring as he said:

"Now rest your head on the pillow for a bit." I realised that, in doing this, I was leaving my bottom sticking up in the air before him, my cheeks parted and my anus fully accessible to him. My stomach churned but I did as he asked.

"Relax Tina. Trust me." Barry whispered. I closed my eyes and tied to breathe more steadily.

I felt a strange wet feeling between my buttocks and realised Barry had poured some lubrication onto my anus. His warm, rough palm began to massage it into my skin and I felt warm. Then suddenly the tip of one finger just broke slightly into the tight grip of my sphincter. I felt my body react, trying to push him out, but he tried gently again and again until what at first felt like the size of a cucumber, but which was in fact only the tip of one finger up to the first knuckle joint, was inside me. He turned his finger around, working the lubrication into my passage. I tried to relax but my stomach was tight and there was a lump in my throat.

His finger still within me, more lubrication was poured onto my cleft and I felt a sudden shock as Barry worked his finger deeper into my bottom. He talked softly as he did so, his voice comforting and reassuring.

"Just going a little deeper now. Just a little deeper. There! One finger all the way in. You are a real virgin, Tina, aren't you?"

I felt at once exposed and vulnerable, but incredibly aroused at the same time. Barry turned his finger around inside me once again. It felt wet and huge and I felt an urge to push against it. I pressed backwards.

"God Tina, you are keen." Barry laughed. "Now the next part is harder. I need to get another finger in alongside. Tell me if it hurts too much." I braced myself both mentally and physically for an invasion. I felt more lubrication on my buttocks and Barry's warm hand stroking my lower back and buttocks as he talked soothingly.

"Now my little virgin, I'm just going to slide my finger in….now." and I felt hard pressure on my anus, prying it open followed by a 'pop' feeling as something large was thrust into me. I felt my body involuntarily trying to push the invader out, but Barry held on firmly inside me until the spasm passed.

"That was a difficult bit. Now I'm just going to get you a bit more used to me." So saying, he twisted both fingers around within me, and moved them in and out a bit. My anus was sore already and the roughness of his knuckles as they passed in and out was making me sorer still.

"Now for a little stretch." And I felt cold air rushing into my insides as Barry forced his fingers apart, stretching my anus as wide as he could, fighting against my sphincter. I tried to relax myself, breathing as slowly as I could while my rectum was violated. Sensing my attempts, Barry stroked my buttocks further and kissed me on the small of my back. "Nearly there. Nearly there."

My guts felt as if I had swallowed a football, so new was the sensation, but there was a further shock to come as, without warning, Barry thrust two fingers from his left hand alongside those from his right. I cried out in shock and pain, and bit hard into the pillow.

"I'm sorry darling. If I'd warned you, you would have tensed up and it would have hurt even more. The worst bit's over now." I whimpered in response, and Barry spoke further, whether trying to comfort me or to turn himself on, I couldn't tell.

"I wish you could se this, Tina. Four fingers in your anus, pulling you open. Making you ready. You're getting so loose, so open. Soon I'll be inside you properly."

And indeed I could feel myself yielding a little. The pain had reduced considerably and although I still felt the need to pee and push his fingers out, the urge was less now. He stretched me cruelly, holding me open with his hands. I felt as if he was tearing me apart. As he stretched me he whispered under his breath "Incredible. Incredible." I felt my body opening.

"It's time, babe. It's time." He at last mumbled in my ear.

I felt his fingers suddenly withdrawn and cold air rushing into me. Barry gasped, then I felt something very large and firm and slippery pressing against my wounded anus. I felt a sudden pressure and with a 'pop' it entered me, stretching me tight. A hard ball of heat began to form in my chest and I couldn't breathe. Barely pausing for breath, Barry pressed further into me and with a terrible burning feeling, I felt my guts being pried apart by a huge invading monster. I began to pant, my breath cut off by the beast in my throat.

"Nearly half way." Said Barry and I felt faint. Surely there couldn't be more. "I'll try and move to loosen you."

As he said that, I felt the monster withdraw from me a little, then come flooding back in with force. I gasped and held the pillow tight against my face to muffle the sound. Again and again Barry moved with difficulty in and out of my tight, dry passage until my hips felt like jelly and I was sure I had peed myself. Barry was starting to grunt with the effort and his thrusts were getting stronger and stronger. I tried to concentrate on loosening up, on relaxing, on enjoying the feeling which was so alien. I was feeling tighter and tighter, the burning getting stronger with every thrust. I thought I would be sick on my pillow.

Then suddenly, incredibly, I felt my body yield. It was as if a tight elastic band had been undone inside me: one moment my body was trying valiantly to expel the invader, the friction burning my insides, the next moment my whole being seemed to open up and welcome him. I felt my sphincter give up the struggle and burst open wide to receive him. Barry must have felt it too as with a powerful thrust he sank deeply into me, burying his whole length in my now welcoming passage.

"Baby! You did it." He said, and his thrusts began in earnest. Sounds of two wet bodies colliding began to fill the room, mixed with Barry's increasingly loud grunts and my own stifled moans. The terrible burning became a wonderful strong warm wet feeling within me and my legs began to tremble beneath his onslaught. My breath came in short pants and within my panties I felt a leaking from my own surprisingly soft cock. Tears of pleasure began to form in my eyes and I buried my face deeper into the pillow. Above the passion I clearly remembered being called 'pillow biter' at school. God if they could see me now!

Barry's passion was driving him hard now, his climax rapidly approaching. He grasped my hips with both hands and his thrusts became even more violent, his balls slapping against me as he hammered into my body.

"I'm going to cum." He gasped.

"Yes." Was all I could mumble in reply. Within seconds I felt the powerful tension in Barry's body break as his hot seed cascaded out of his cock and into me. His body, racked with the spasms of his orgasm, twitched and trembled as his semen poured into my ass. His spasms slowed and with a sigh he collapsed across my back, pressing me face first into the bed, his cock still firmly within me. We lay in silence, motionless for a while, catching our breath.

"That was fantastic." He finally breathed into my ear. "Just the best." I felt really good inside as he softened within me. At last he put his hands on the bed, either side of my head, and raised himself up, gently pulling his flaccid cock out of my rectum.

He rolled alongside me. I rested my head on his shoulder, my long hair across his chest and he put his strong arm around me. I was trembling with excitement and the incredible feelings he had produced within me. Exhausted, we dozed for half an hour before the cooling air in the room roused us. Barry kissed me on top of my head.

"Bed time, darling." He said. I carefully stood up and walked unsteadily, my knees still weak, across the room to the bathroom. I closed the door and, leaning on the sink, looked apprehensively in the mirror. My hair was ruffled, my lipstick smudged, my eye makeup runny. There were red handprints on my hips and fingernail marks on my back. My buttocks were beginning to show bruises.

I felt deliriously happy.

Blessedly, my stockings were undamaged and I unfastened my suspender belt and rolled them down and off. The bra followed quickly. My skin coloured panties were still tightly in place. I carefully pulled them aside to allow my cock to hang down and I sat on the toilet to pee. As my buttocks parted, the cool air hurt my sore rectum. I reached down to touch myself and found my anus still gaping open. When I looked at my fingers I saw blood along with the white sticky fluid that dripped from me. Semen, I thought. My lover's semen.

I carefully removed my wig and locked the door then turned on the shower and stepped inside. The warm water felt wonderful and I washed myself all over with lots of shower gel, feeling my aches and bruises melt away. The soapy suds made my newly ravaged anus sting, but I didn't care. At last I turned off the water and dried myself on a large fluffy white towel. I pulled on one of the bathrobes hanging on the back of the door, carefully secured my wig back on my head, and stepped back into the bedroom.

The room was in darkness. Light from the bathroom shone directly across the bed and I saw Barry asleep neatly on one side under the bedclothes. The sheets on the other side were turned down to welcome me. I turned off the light, tiptoed across the room, dropped my robe and slipped naked into bed beside Barry where I snuggled close to his warm powerful body. I fell asleep.

I opened my eyes to the sound of the room's kettle boiling. Barry stood near the window, a white towel wrapped around his waist, making tea. He turned towards me.

"Good morning – Tina?" he asked, his intonation asking me to confirm I was still a girl. I nodded, feeling disoriented, unsure how to greet my new lover. "Tea?" he asked. I nodded again.

"Mmm Please."

"How do you feel this morning?" He asked, his voice showing he really wanting to know.

"Sore, I'm afraid. And a little battered."

"I'm sorry. Perhaps I got carried away."

"No!" I insisted. "You were perfect. I couldn't have asked for more."

"And you don't regret it?"

"Not one minute, Barry. I loved it all."

Barry carried the two cups of tea to the bed and sat down. I sat up next to him. We sipped the hot liquid in silence. It tasted horrible and we both burst out laughing. My giggles made me wriggle on the bed and a burst of pain from my bottom shot through me. I winced.

"Will it always be so painful?" I asked, unconsciously assuming there would be other occasions to find out.

"No darling. You're not a virgin any longer. As long as you don't go too long without .. someone … your body will get used to it. Eventually it won't hurt at all – it will all be pleasure."

"I'm really glad my first time was with you." I said, running my fingers down his muscular arms. "You were so gentle for such a strong man."

"I couldn't have been anything else with you." He kissed me lightly on the lips, then kissed me again more passionately. Our mouths opened, our tongues touched and we melted together again. Barry pushed me back on the bed and lay alongside me, his face over mine, kissing me deeply. My arms went around his back and my legs rose. His towel fell away from his body and his cock rose strong and proud before my eyes. I felt overwhelmed with desire, my newly experienced body aching for him again. I kissed him with real passion as he deftly manoeuvred himself between my legs. He knelt between my thighs and looked down on me. I smiled, my long hair fanned out over the pillow, naked beneath him.

Reaching over my shoulder, Barry took the tube of lubrication from the bedside table and spread some on his fingers. Looking me straight in the eyes, he began to rub it over his erection. I arched my back a little, desire filling my eyes. He placed a hand under each of my knees and lifted them up and apart. My legs bent and opened wide, exposing my panty-covered genitals and my reddened rectum. Barry spread more lubrication on his hand and began to massage it into my soreness. The coldness of the jelly made me gasp, but compared with the burning it felt wonderful. Barry's fingers slipped easily into my anus, still weakened by the previous night's lovemaking.

"Now let's do it properly." He said hoarsely, and lowering his body between my knees, placed the tip of his cock against my aching entrance. He pressed himself into me.

My body opened immediately to welcome him. Joy must have shown clearly on my face as he slid smoothly his full length into my warm, moist channel because his face, merely inches from mine lit up with delight. My legs rose and wrapped themselves around his slim waist, leaving him free to plumb the deepest recesses of my body. I felt him drive powerfully into me until his wiry pubic hair grated against my sore buttocks. I traced patterns on his strong chest with my fingernails and felt moisture running down my cheeks. He rested in me, giving my body time to adjust. I felt his invasion in my belly, in my chest, in my throat. I stroked his face as he smiled at me and held him tighter with my legs.

He began to pump in and out of me in long, smooth thrusts. I looked into the face of my lover as his muscled body drove his cock into and out of my abandoned anus and rectum. Over and over, his measured strokes brought delight to my insides as again and again his large cock penetrated me, the pressure against my prostate bringing pleasure beyond description. Ripples of warmth emanating from my insides flowed through my whole body. His strokes gradually became faster and harder and my own pleasure became stronger and sharper until with a groan, his face screwed up tightly and with one, two, three fierce thrusts that banged my head hard against the bed head, I felt once again his warm, sticky release within me. His body went stiff as the last few drops of semen were pumped out of him, then he gently lowered himself on top of me.

His weight pressed down on my body and I loved it. My arms encircled him and I hugged him close, feeling his muscular chest pressed against my own, his firm biceps either side of my face. His eyes were soft and dewy as he recovered his breath, and never left mine. My legs wrapped themselves tightly around his motionless body as if afraid to release him. I felt his erection, deeply embedded within me, retreating slowly as he softened inside me. Sweat from his forehead dropped onto my face, salty and fresh. I smelt his masculine body, felt his powerful frame and wondered at the intensity of this new joy in my life.

Showered, make up removed and dressed once again as a boy in my tight jeans and a white T shirt, I followed Barry's masculine frame into the dining room for breakfast. The girls were seated in the window at a table for four and we crossed to join them. Debbie looked up at me questioningly and raised her eyebrows. I smiled and nodded, noticing the flushed look on her cheeks. We had agreed not to ask each other any questions about our night time activities, but we each had the other's mobile number programmed into our phone in case of emergency or extreme unhappiness. Neither of us had needed it.

I sat down gingerly opposite Monica and ordered coffee. Barry preferred tea. The room was light and busy, the breakfast buffet against the back wall. After a few rather stilted 'Good mornings', Barry stood and crossed to the food table, followed by Monica. Debbie leaned across the table to me.

"How was it?"

"We agreed not to ask!"

"Go on – you look half stoned, and you're walking funny!"

"What?" I almost shouted, horrified. Debbie was giggling. "Well … it was great. Really great! Thank you so much for … for … well, for everything." I kissed her lips across the table. "But I am sore." I blushed. "How did you get on?"

Debbie looked dreamy eyed herself. "Monica is a lovely person." She said enigmatically.