I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had only been with Barry when the four of us had spent the night in a hotel together. The thought of just the two of us meeting was exciting. I wasn’t sure why I wanted it to be a secret; perhaps I thought that Debbie wouldn’t want me to go if she wasn’t seeing Monica as well. Anyway, it now felt like a secret affair. I felt a bit guilty, but only a little bit.
Barry was in town for a business meeting that day. He didn’t usually get this far north, but a potential new client was based in our city and Barry was meeting him that morning in a hotel on the outskirts of the city. He had asked me if I could get off work for the afternoon and meet him there in a room he had rented for the day. Debbie and I work flexi-time so it was simple to arrange for a colleague to cover for me for the afternoon. I left work at noon and stopped off in the town centre to buy something special to wear. It was safely hidden in my briefcase as I made my way home. I had arranged for Barry to pick me up in his car outside the flat I shared with Debbie at 2 o’clock, which looked like giving me an hour to get ready. It would have to be enough. In my tummy, the butterflies were going crazy.
After what seemed an age, the bus drew up at my stop and I hurried along the pavement to our block. Opening the main door, I ran upstairs and hastily unlocked our front door, closing and locking it behind me. I went quickly into the bedroom and put my bag down on the bed. I breathed out heavily and, in my mind, ran over all I had to do whilst I unpacked my bag and spread my purchases over the bedspread.
To cut a long story short, I prepared myself as carefully as I could. I wanted my first solo meeting with Barry to be as perfect as possible. His voice on the phone that morning had been soft, warm and conspiratorial and had turned my legs to jelly. I yearned to feel his strong, muscular body close to mine again, to be courted and seduced and (I so badly hoped) to feel him inside me once more. I felt my face flush and went through to the bathroom.
I bathed thoroughly, washing and conditioning my hair (at this time barely shoulder length), and carefully shaving my body all over. I rinsed myself down with the shower head and dried on a large bath towel. I looked myself over in the bathroom mirror. Slender and lightly tanned, I lacked the rounded curves of a real girl’s hips and breasts, but thanks to Debbie’s tutoring my movements and mannerisms were close to perfect. I turned to look at my slim thighs and smooth, slightly pointed buttocks. I had done all I could. I hoped it would be enough for Barry.
Lightly perfumed and moisturised, I dried my hair with Debbie’s dryer and returned to the bedroom to dress. As before, I used my fingertips to slip my testicles upwards and inside my body, folding my cock downwards over them. I reached down to the bed and carefully pulled on the new white silk g-string I had bought that lunch time. It felt cool and smooth against my shaven skin and I felt very sexy, the thong between my buttocks tickling my cleft and anus deliciously.
Over my head I slipped a new yellow crop top and pulled it down over my chest. Its ragged lower hem reached down to a couple of inches above my belly button. I took my last purchase through to the bathroom with me and inspected myself in the mirror. My lack of breasts was not too obvious under the crop top, and I was pleased and relieved with what I saw. Thanks to weekly gym sessions, my chest and tummy were slim and well defined and ran smoothly down from the top’s hem to the top of my silk panties. I stroked my skin tenderly, imagining Barry’s fingers doing the same. I felt warm all over.
Satisfied, I opened the last bag and took out a short denim skirt. I stepped into it and pulled it up, fastening the zip and button over my hip. I smoothed it down and looked again in the mirror. Golly, it was very short! Falling straight down at the front, it hugged my buttocks closely, showing their firmness in a way that pleased me and I hoped would delight Barry. My legs looked slim and pale beneath it. I felt even more feminine. Oh, Barry! I hope you like it!
I carefully applied a little eye make-up and lipstick, and brushed my hair until it shone. I looked at my watch. Five minutes to two. I felt slightly sick with excitement and anxiety. Skipping back into the bedroom, already unconsciously moving in a feminine way, I peeped out of the window. No car yet. I turned to sit on the bed and pulled on a pair of low cut white socks before slipping on my new white trainers. I stood up and, for the last time, checked my appearance.
A horn sounded outside and, looking out of the window, I saw Barry sitting in his silver sports car parked cross the entrance to the driveway. Whatever I looked like, it would have to do now! Despite the hot weather, I pulled my long raincoat around me and ran downstairs to meet him.
As I skipped down the driveway, Barry leaned across the car to push open the passenger’s door. I pulled it wide and sat down next to him, drawing my knees and feet in daintily. I closed the door and turned towards him. Pleasure was written all over his handsome, tanned face. He leaned over and we kissed each other on the lips.
“I’m really glad you could get away, Tina.”
“So am I,” I smiled. Barry lifted my chin with his index finger and kissed me again, this time his tongue parting my lips and seeking my own. He found it and for an electric moment our tongues entwined. He tasted of mint. Clean and fresh. I loved it.
He stroked my right thigh momentarily and started the engine. He pulled away and we drove through the city towards his hotel.
“You look great, Tina,” he told me. “Aren’t you hot in that coat?”
“A bit,” I confessed, “But I’ll be OK. How’s Monica?”
Barry looked awkward. “She’s OK.” His voice was strange – slightly stilted.
“Does she know you’re here?” I asked.
“Well… Not exactly,” he replied. I heard the guilt in his voice.
I felt oddly pleased by this. “Barry…” I said, “I haven’t told Debbie either.” He looked relieved and squeezed my leg again, running his hand up towards the hem of my coat.
We traveled in silence to his hotel, finding a parking space close to the entrance. Barry jumped out and, like a true gentleman, opened my door and took my hand to help me out. As I stood beside the car, I took off my coat and threw it onto the seat. I straightened my crop top and smoothed down my skirt.
“God, Tina. You look sensational.” Barry spoke breathlessly.
“Am I good enough?” I asked, looking him in the eye, “Do I pass?”
In reply, Barry kissed me tenderly on the lips right there in the car park, his tongue working its way into my opening mouth. When our lips parted, he took my hand and led me boldly through the hotel front door and into reception. As we crossed the lobby, his hand released mine and slipped down to my buttocks where it stroked my cheeks through the denim as we walked.
I felt very good.
We crossed the busy lounge and passed through a heavy fire door into a long corridor. Barry ushered me along, past several other guests who were going in the opposite direction. They didn’t appear to notice anything amiss. I turned to see if they looked back over their shoulder at me, but they didn’t. Barry must have sensed my relief because his fingers stroked the back of my thigh just under the hem of my short skirt.
We arrived at his room and he opened the door clumsily. We went in. The room was quite small and dark, but had a good sized bed and a small private bathroom, tiled in fake white marble. I crossed to the window and looked out over a well cut lawn fringed by tall trees. It was very private. I heard a ‘pop’ behind me and turned to see Barry opening his customary bottle of champagne and pouring two glasses. He smiled broadly and handed one to me.
“Nervous?” he asked, sounding nervous himself.
“A bit,” I confessed. “Not about being with you, but Tina’s never been out without Debbie before.”
He took my hands in his. “You look just perfect. Nobody knew – and some of the men in the lounge were eyeing you up.” I smiled. I thought I’d noticed that, too.
Barry led me to the bed where we sat and sipped our drinks slightly awkwardly, neither knowing quite how to go from here. When we had been together before it had always been in the evenings and we had both been a little drunk. Now, sober and in the afternoon, it seemed different. If anything, I thought, Barry looked even more gorgeous in his suit trousers, white shirt and tie. His clothes were obviously tailored and fitted his athletic body to perfection. I ran my fingers through my long hair as Barry placed a soft palm on my knee, stroking my thigh gently as his hand rose up my leg towards the hem of my skirt. I stroked his cheek with my fingers.
“Just a minute, darling,” I whispered. I rose slowly, my fingers remaining on his cheek, and walked across to the bathroom. His hand rose up the back of my thigh as I passed him, and I could see his excitement when he felt my bare buttock rather than panties. I entered the bathroom and closed the door.
Breathing out in an attempt to control my excitement, I turned towards the toilet and, raising my skirt, I slipped my g string to the floor and sat down. I couldn’t go, my excitement was too great, but I took the opportunity to take further precautions. (I had already lubricated myself ‘down there’ before leaving home, but seeing the look on Barry’s face, I took a tube from my handbag and liberally applied more.) I stood and flushed the unused toilet, then stood in front of the sink to straighten my clothes in the large mirror on the wall.
I was still pleased. Growing my hair longer had been a good idea – it fell onto my shoulders softly and smoothly. The crop top was tight across my shoulders and chest, and between it and the skirt waistline my stomach was smooth and flat. One day, I thought, I would get my navel pierced. Barry would like that. The skirt had been a stroke of genius. It was tight and hugged my buttocks, its length barely covering them. I had worked hard on my legs and they were now slender and tanned.
I was just checking my make up when I heard the door behind me opening. Barry slipped silently into the bathroom behind me. I did not turn around. I did not need to because the mirror showed me the whole room in reflection. Barry was smiling and I saw that he had undressed right down to his white boxer shorts. I drew in my breath sharply. It seemed like a long time since we had been together and he had not wasted it. If anything, his arms and chest were even more muscular, his waist even slimmer, his leg muscles even more well defined. His skin was bronzed, almost golden. I ached for him.
I dropped my eye liner on the marble top and, watching Barry in the mirror, felt his hands lightly hold my upper arms. I saw him lower his head and felt his warm lips brush against the nape of my neck as his fingers stroked the smooth skin of my torso beneath my top. I tipped my head on one side and, crossing my arms over my chest, leaned back against his warm body. He kissed my cheek and his arms slipped around me. In the mirror I watched as his right hand moved upwards under my crop top to seek my small, hardening nipples while his left hand moved in tiny but increasing circles across my lower belly. I could smell his aftershave and just a hint of sweat. It was very arousing.
I opened my arms to allow his hand to fully explore my chest, and reached behind me to caress his slim waist. In the mirror I watched with eager anticipation as his left hand moved down to press against my upper thighs through the soft denim of my skirt. I wriggled my buttocks against his groin and he moaned under his breath. His hand descended to the hem of my skirt and, lifting it gently, sought out the waistband of my panties. As his hand rose I watched the mirror entranced as the curtain of my skirt was raised to slowly reveal my white g string beneath. Barry must have seen it too because his urgency suddenly increased.
His cool fingers deftly found the top of my panties and even more deftly slipped inside. I felt and watched as his silk covered hand descended across the sensitive, smoothly-shaved skin of my lower belly and deep between my thighs. His large palm, strangely warm compared with the coolness of his fingers, cupped my cock and balls. I felt weak and leaned more heavily against him as he gently ran his fingers over my genitals. My eyes closed and I felt warmth wash over me. To my surprise I felt myself becoming erect under his soft touch as he toyed with my baby-smooth tightening testicles and hardening cock.
I reached behind and fumbled for his boxer shorts. Through the cotton, Barry’s erection felt huge in my hands. I found the waistband and after a struggle, slipped my hand inside. I grasped his cock in my hand. Surely he had never felt this big before! My hands are not large, I know, but I could barely close my fingers around him. My knees went weaker still and my body began to yearn for his body.
As if sensing this, Barry’s left hand dived deeper down between my thighs until his long middle finger found the rim of my anus. I gasped at his touch. Pushing further down, his fingertip slipped easily into my anus and in the mirror I saw a puzzled look on his face as he discovered the lubrication and realized the lengths I had gone to prepare for him.
“Tina?” he asked.
I blushed a deep red. “I wanted to be ready for you,” I replied. He kissed me again on the neck and gently withdrew his finger.
I watched in the mirror as, without a word, he placed his hand between my shoulder blades and pressed. I obediently bent forward over the sink, my hands grasping its edges, my denim-clad bottom presented flagrantly to Barry. He hesitated then, almost in slow motion, lifted the back of my skirt right up and laid it along my back. I felt slightly cooler air on my bare, exposed buttocks and imagined Barry looking down at my pale cheeks and the even paler white thong passing between them over my anus, made even more sensitive by the abrasion of the silk and Barry’s welcome invading finger.
Barry’s hands grasped the waist of my panties and pulled them down to rest just below my buttocks. The sensation of air on my anus was wonderful. I felt very vulnerable but at the same time very excited. My erection, freed from the panties, slapped against my lower stomach.
Barry pushed my trainers further apart with his feet and my sense of vulnerability increased. His hand began to massage my cock and balls again from behind and I heard myself moaning softly. A single finger invaded my anus and I pressed against it, my eyes never leaving Barry’s reflected face in the mirror. My body was crying out for him. There was a pause and I watched as Barry released me and pulled down his boxers to his knees. Oh, God! It’s going to happen now, I thought.
The sight of Barry’s released erection shook me. No stranger to his cock, I had never seen it so big or him so excited. His eyes were fixed on mine as I felt his head being positioned against my anus. My knees began to tremble in anticipation and fear and I gripped the sink harder, waiting for his first stroke.
I did not have to wait long. With a grunt, Barry heaved his body forward. I held myself as still as I could and with a ‘popping’ feeling the head of his mighty cock broke through my resistance to enter my rectum. I felt my sphincter tighten around the ridge behind his head. He paused. I breathed again. He felt simply enormous within me, filling me completely. It was wonderful.
But the pause was only short. Barry increased his pressure again more firmly and I closed my eyes and breathed out slowly as inch by welcome inch, he embedded himself in my body. His erection was stretching me as never before and I felt warm and whole and fulfilled as his erect cock sank its full length into my welcoming ass. My own erection immediately softened as my feminine side took over and my body opened for my lover. The stiffness and resistance of my body to our first lovemaking was now a thing of the past; my sphincter gladly opened to receive him and as his massive bulk reached its limit, I felt with joy the roughness of his pubic hair against my cheeks as the wide base of his shaft stretched me wider than ever before. I felt the warmth of his thighs pressing against the back of my own. My hands, still gripping the edge of the sink, relaxed a little and I opened my eyes to see Barry’s reflection in the mirror before me. His eyes were fixed on mine.
“Shall I… fuck you, Tina?” he said. I was surprised by the crudeness of his words, but they aroused me more. I nodded.
“Say it, Tima!” he commanded.
“F... f… fuck me, Barry!” I croaked. He smiled lustfully.
Slowly, he began to move in and out of me. I felt a dreadful emptiness as he withdrew, followed by gut wrenching joy as he thrust back into me. I panted in time with his thrusts and as his pace gradually increased, my pleasure increased with it. The sounds of his body slapping against mine grew louder, his balls colliding with mine on each inward thrust and I heard myself panting and moaning, small, high pitched grunts escaping my throat. I looked into Barry’s face in the mirror and saw it screwed up in pleasure as I had never seen before. His pace quickened and I began to feel friction within me as the force of his penetration grew.
I looked up in confusion to see if anything was wrong. Before my eyes, an animal-like anger seemed to grow within him as his excitement increased. I began to feel a little frightened, completely exposed and at the mercy of this powerful, lustful man. Suddenly I felt Barry’s movements change. His thrusts became much harder and more violent and he began to grunt loudly with each thrust. It began to hurt me - just a little.
“Barry... Be gentle... Please!” I whispered but he can't have heard me over his loud, sharp grunts and fast thrusts.
Through eyes clouding with tiny tears of pain but still a great deal of pleasure, I saw in the mirror his face screwed up with lust as he lost the last remnants of control. Not wanting to fail my wonderful lover, I leaned further over the sink, my forearms now resting along its edges, my hands grasping the taps to brace my body against his onslaught. Barry was reaching a shattering climax. His face was a picture of pure lust as he used his powerful thigh muscles to drive himself into me over and over again.
I bit my tongue as new sensations began to flow through me. Barry’s thrusts lifted me onto my tiptoes every time he drove his hard cock into my rectum and my head banged into the wall with each blow. My long hair fell across my face making it hard to see in the mirror and my ass burned with friction as the lubrication began to fail. A hot wet feeling spread outwards from below my anus, along the inside of my thighs and up into my stomach. I looked down between my legs and realised that despite my soft cock, the repeated pounding of my rectum and prostate had made me cum. Semen was dripping from my swaying cock into the panties around my thighs.
Still Barry hammered into me. His hands now gripped my hips and as his climax finally hit him he shouted incoherently out loud. His final thrusts lifted me bodily from the ground, impaled on his massive erection, my white trainers barely touching the floor. I felt torn open, helpless and abused.
At last to my relief his passion broke and he began to cum inside me, his body twitching as I felt cascades of semen filling my ass, and running in long sticky streams down the inside of my thighs as finally his thrusts slowed and stopped.
The room felt still and silent as Barry’s erection throbbed its last few spasms within me. I felt overwhelmed, the forece of his lust having taken me wholly by surprise, my bottom already feeling very sore.
Barry lowered my feet to the floor as his erection gradually softened. I tried to take my weight on my legs but they trembled too much. As he silently pulled his now flaccid cock out of my ravaged ass and turned away, my knees gave way and I sank to the bathroom floor, panting for breath, trembling from shock and my own unexpected climax.
Small tears running down my cheeks, we sat in silence, both unsure what had just happened.
“Tina,” Barry suddenly swung round to face me. “Tina, I’m so sorry. I’m so sorry.” I couldn’t reply. His voice sounded choked as he went on. “I don’t know what came over me.”
Still I could not respond, my mind and body in turmoil.
Barry stood up unsteadily and offered me his hand. I didn’t move. He then bent over and to my surprise picked me up bodily, carrying me through to the bedroom where he laid me on the bed. I didn’t resist, but laid there motionless, my hair across my face, my skirt rumpled up around my waist, my knees dawn up in front of me, my panties still around my thighs. He sat alongside me and gently stroked my hair and despite the pain in my ass, I began to feel a little better. My crying stopped.
“Tina, I’ve never been so turned on in my life,” he whispered. “I just couldn’t stop. I’m so sorry. I would never hurt you, I love you!”
Relieved beyond belief, I reached out to him and pulled him onto the bed next to me. We hugged each other in silence, our bodies at first stiff, then moulding together. The pain in my ass gradually became less important. The fear in my mind was fading less slowly.
“I wanted you so much, but when you started to hurt me, I thought it might be because you found me disgusting.” I eventually said. He shook his head.
“How could you even think that? You’re beautiful, Tina.”
I was still shaken and although I didn't want to leave, I felt tense and a little frightened at the passion I had released. Barry hadn't been repelled by me - that was a relief - but the strength of his desire had caught me by surprise. I was confused.
On the one hand it made me feel good that I could stir such powerful feelings in a man I felt so attracted to.
On the other hand, I had been physically hurt by the results of that passion.
On the third hand he had definitely made me cum too.
We lay in each other's arms for a long time until my body lost some of its tension and it was time for him to take me home.
About two weeks later, Barry called to arrange to see me again. I think he was expecting me to refuse, but I agreed. I met him as Tim and we had dinner together in a local restaurant. He was still shaken by his loss of control and unsure whether he had destroyed our relationship. We talked for a long time before going back to his hotel and, very gently, making love – this time as Barry and Tim. It was my first time as a man. It was gentle, considerate and loving.
But I prefer being Tina for him.
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with this note attached, it has been posted without my permission.
<a href="http://www.lushstories.com/stories/crossdressing/first-night-nerves-part-2.aspx">First Night Nerves - Part 2</a>