Bobby and Chrissie Part 1
The girly adventures of two pretty boys.
When I was at Nottingham High School I didn’t have many friends as I was a skinny, sort of feminine boy. In my second year, when I was twelve, a new boy arrived. His name was Robert. He wasn’t like most of the other boys, who were mostly masculine boy-type boys. Robert was very slender and rather girly, as I was. We were both teased unmercifully a lot for being sissies; we became firm friends throughout school. We hung out a lot together, finding strength in each other’s company. We both grew our hair really long, making us look even more feminine. Robert was very pretty for a boy, with long, blonde, wavy hair; at twelve he could easily have passed as a girl. My own hair was dark brown and very long and I was quite girly looking too. We were often mistaken for girls when we went out together.Shortly after I met Robert I started calling him “Bobby”, as it suited his sweet nature better. He didn’t mind, in fact he liked it. He started calling me “Chrissie” which I liked much better that plain “Chris”.We remained close friends all through school. I would often go to Bobby’s house and hang out after school; we were both twelve then and liked to play games on his computer. Bobby’s dad had left when he was five and he lived with his mum. She was blonde, slender and very pretty. Bobby looked just like her. I wondered why she had never re-married; I found out later she preferred girls and had a girlfriend. She seemed to like me a lot. “Chrissie, come and sit by me,” she would say, “let me do your hair.”She delighted in brushing my long hair and styling it. Her vibes were so relaxing that I let her do anything to me. Once she put my hair into pigtails and tied them with little pink ribbons, making me feel wonderfully girly.“Bobby, see how pretty Chrissie looks,” she said.Bobby turned from his game and looked at me. A surprised little smile spread over his little face. I felt myself blushing.“Oh,” he said, “you look nice, Chrissie.”“I feel a bit silly.” I said.“Don’t feel silly,” Bobby said, “you look great. Anyway my mum does that to me all the time.”“Really?” I said, feeling a strange excitement.“Yes. Bobby looks lovely in pigtails,” she said, “like a little schoolgirl.”Now it was Bobby’s turn to blush. He gave me a sweet little smile and lowered his eyes shyly.“You two would make great little girls,” his mum said, “you’re both so pretty.”She fiddled with my pigtails, adjusting the ribbons and brushing them softly. I think she would have liked a daughter. I suppose Bobby was the next best thing.I remember one special day I went over to Bobby’s house. I was thirteen by then, as was Bobby. It was the first day of summer holidays and very warm out. I had on a little pink tank top (my mum's) and some cut-off jeans. It was so nice not to wear my ugly school uniform. I trotted happily over to Bobby’s house and knocked on his door. I knew his mum wasn’t in; she had gone to visit her mother in Grantham and wouldn’t be back until the following day. We could get up to all sorts of mischief, as little boys do. Bobby answered the door with his usual pretty smile. I stood looking at him with my mouth open. Gone was the hated school uniform. He had on a loose-fitting red top with a wide, low neckline, and very brief pale blue shorts. His mass of long, blonde hair was tied up high in a girl-style ponytail with a big pink scrunchie. To my surprise, he was wearing red nail polish. The whole effect was extremely feminine. I loved it. He reached out and took me gently by the hand, leading me inside.“I love your nails,” I said.“Thanks,” he said, “it’s called ‘Affair in Red Square’ by OPI.”We walked through into his living room and sat on the couch together. I took his hand and examined his nails.“You did them really well,” I said, “how did you manage that?”“My mum taught me,” he explained.“They look so pretty,” I said.“I did my toes too,” he said, “look.”Bobby lifted one slender leg daintily and showed me his shiny red toenails.“Oh, that’s beautiful,” I said, “I’m amazed.”“Do you want me to do yours?” he offered, “I have a colour that would be great on you. It’s a soft pink. It would go great with that cute top you’re wearing.”“OK,” I said, thrilled, “well, maybe just my hands.”Bobby rummaged through a little bag and produced a small pink bottle with the letters OPI on it.“Hold out your hand,” he said, and I obeyed.Bobby carefully and expertly applied the pink polish to all my nails. The effect was lovely. I was feeling more girly by the minute.“Don’t move for ten minutes,” he commanded, “or you’ll wreck them.”He gave me a sweet little smile sat back, pleased with his handiwork. As he did so, his top slipped down, exposing one slender little shoulder, making him look even more feminine. He gave me a sweet, shy look, but made no attempt to pull it up. I noticed, not for the first time, how long and pretty his eyelashes were. Even though he was a natural blonde, his eyelashes were dark.“I love your top,” I said.“It’s my mum’s,” Bobby said, “I love the neckline.”He looked so cute with his bare shoulder peeping prettily out. It was such a feminine effect. I wondered if he realised how sexy he looked.“Your shorts are nice too,” I said.“They’re actually hot pants,” he said, “low rise.”He lifted his top, showing me his slender waist and flat tummy, and the cutest little tummy-button. The shorts were very low and almost showed the top of his pubes.“Very sexy,” I said.He gave me a sweet smile.“It’s my mum’s stuff,” he said, “I’m always wearing her clothes. We’re the same size.”“I wouldn’t wear that at school,” I said, “you’ll get killed. Or worse.”“I know,” he said, “but here I can do what I want. You can too.”We sat together for a while like little girls, looking at our pretty painted nails. Two sweet little boys enjoying being feminine together.“I feel pretty now,” I said with a giggle.“Isn’t it nice?” he said.“I love it,” I said.“We could be even prettier,” he said.“How?” I asked, curious and excited.“Back in a minute,” he said.Bobby got up and disappeared upstairs. A few minutes later he reappeared holding of all things, a tube of lipstick and a compact. “Mummy’s makeup,” he said with a little giggle, “she lets me borrow that too.”“You wear lipstick?” I said, astonished but secretly thrilled.“I love it,” he said.He sat down next to me, opened the compact, and, looking in the little mirror, applied the soft red lipstick to his pouting mouth. He pressed his lips together like a girl and looked at me coyly.“What do you think?” he asked.“Ooh, that’s pretty,” I said, “it makes your lips look really nice.”“Want some?” he asked.“Er, I don’t know,” I said in feeble protest.Chrissie you’ll look great,” he said, “go on, try it.”“Will you put it on me?” I asked, “I don’t know how.”“Of course,” he said.Bobby moved closer and I presented my mouth to him. My heart was pounding.“Pout your lips a little,” he said.I pouted obediently.“Ooh! You have such a cute mouth,” he enthused, “just like a girl. Perfect for lipstick.”Bobby didn’t know how good he was making me feel. I secretly wanted to look pretty for him. He applied lipstick to my waiting lips gently, coating them heavily with the soft red colour.“There you are Chrissie,” he said, “look how sexy it makes your lips.”He passed me the compact and I checked myself out. My lips looked luscious, full, shiny and very kissable. Sexy indeed. I felt my heart beating fast. Young boys wearing lipstick and nail polish. How exquisitely naughty! I loved it.“Have you ever kissed a girl?” Bobby asked me suddenly.“Only Michelle Elliott,” I said, “she's from the girls' school next door. I walked her home a few times and we kissed on her doorstep. It was nice. I don’t really know how to kiss properly though.”“It’s easy,” Bobby said, “my mum taught me.”“Your mum?” I said, astonished.“Yes,” he said, “I asked her how to kiss a girl and she showed me.”“You kissed her on the lips?” I said.“Yes, we practised kissing for ages and ages,” he said, “it was lovely.”“Your mum is really pretty,” I said, “I wish I could get a kissing lesson from her.”“I could give you one,” he said.“But you’re a boy,” I said.“I know,” he said, “but I could pretend to be a girl for you.”I looked at Bobby’s beautiful, girlish mouth. His soft, red lips looked so inviting. He was so much like a girl anyway. Kissing him would be heavenly."Come here then," he said softly.I moved slowly, nervously closer to him until our lips were just inches apart. “OK Bobby, teach me then,” I said with a nervous giggle.I closed my eyes and waited. After a few moments my heart leapt as I felt the soft touch of his lips on mine. My sweet little Bobby was kissing me! His lips felt soft and lovely. Nicer even than Michelle’s.“Open your mouth a little,” he said softly as we parted briefly.I parted my lips a little and we kissed again, tenderly, delicately, for much longer this time. The lipstick made our soft young lips slide together so deliciously.“Oh, Chrissie you sweet boy,” Bobby said as we parted again, “you kiss just like my mummy.”“I love it,” I said, “let’s kiss some more.”“Do you know about french kissing?” Bobby asked.“I’m not sure,” I said.“I’ll show you,” he said, “it’s really sexy. Open your mouth a little bit more.”He took my hands gently in his and came towards me slowly and once again sweetly touched his beautiful, girly mouth on mine. We kissed softly, our lips parted. Suddenly I felt the tip of his tongue on my lips. I opened my mouth wider and he slipped his tongue gently in. So this was french kissing! It was lovely. I slid my tongue inside his mouth too and our tongues played gently with each other. Our kiss became very wet and sexy. We sucked each other’s tongues and licked each other’s lips. I knew boys weren’t supposed to do this with each other, but I didn’t care. I loved being a little sissy and kissing this sweet, feminine boy. After the most gorgeous, wet, girly kiss of my life, we parted, breathless. We looked into each other’s eyes knowing we would be kissing a lot more from now on.“Thanks for the lesson,” I said.“You don’t need lessons,” he said, “you’re a natural.”He reached out and touched my lips with his fingertips.“I smudged your lipstick,” he said.“I smudged yours too,” I said.“It’s OK,” Bobby said, “we can put more on.”He got the lipstick and his little mirror and I watched closely as he put some more on. I loved watching him pout so prettily as he painted his lips. “Try putting some on yourself,” he said, handing me the little black tube and mirror.Watching myself in the mirror, I took the lipstick and applied it as I had seen him do, pressing my lips together. It was easier than I thought. It was such a lovely, girly feeling to put lipstick on. I turned to Bobby and pouted for him as girlishly as I could."See, you're a natural girl," he said."I need a few more kissing lessons," I said, "just to make sure."We kissed again, tasting each other’s lipstick, our tongues sliding naturally into each other’s mouths, licking the lipstick off each other’s lips, wet, lovely kisses, so tender and delicate. We couldn’t stop kissing each other; we kept putting on more lipstick and french kissing again and again until we were totally out of breath. We sat holding hands, looking into each other’s eyes, our lips wet from our delicious kissing. Two sweet feminine boys in girlie heaven. The fact that we were both boys was thrilling and so naughty. Little did I know how naughty it would get. If you liked this story email me at sweetlissy2001@yahoo.co.uk