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First time sex story - I was eighteen before I worked up the courage to let a boy fuck me! I am a good looking girl, petite with long blonde hair and green eyes and a pair of firm 34C breasts but I avoided going out alone with boys even though many of them at school were clearly attracted to me. My girl friends would tell me how boys had fondled them, pressed their tits, stuck their hands into their panties and rubbed their pussies and how they had put their hands on boys' "things" and rubbed them till they spurted thick white goo up into the air. These stories did not excite me. I always found boys rough and inconsiderate and was afraid their "things" would hurt me.
I grew up in a single family home the only child of a mother who loved me dearly. All her friends were female, either single or couples with children about my age. My father was never mentioned but I got the impression that he had some how wronged my mother and even beaten her often before they eventually separated. My earliest memories of all the parties my mother took me to had only women and their children present and most of the children were girls.
My best friend Susie lived with her mother and her "friend". Susie told me that they shared a bedroom and she slept by herself in another bedroom. They were partners in a very successful boutique and seemed to be quite fond of each other. They never quarreled and were always smiling and sweet tempered. Susie and I were inseparable and our mothers were close friends too.
As the two of us grew out of childhood we began to realize that other kids did not live the way we did. There were more males in their lives and couples were always a man and woman. Many of the girls at school spoke about their dads and brothers and when we were invited to parties at their houses lots of males were present. Both Susie and I found ourselves very uncomfortable at these parties and stuck together for support and comfort.
Once at a sleep-over at Susie's house we began to talk about boys and how we did not like them and Susie said that she had to tell me a secret. I promised not to tell anyone and she told me she had a brother, a year older than her, who lived with her father and who visited them secretly and alone as her mother loved the boy and could not tear herself away from him. She also confessed that she too was very fond of him and when ever he stayed the night he shared her bed. They had slept together from the time they were babies and thought nothing of it. In fact he slept in a flimsy nightdress she lent him!
The thought of Susie and her brother sleeping in the same bed excited me and the next time I was over at her place I asked her about it.
"Does he just lie quietly and talk to you or do you both fondle each other like we do" I asked her curiously.
"Does he rub your pussy and make you feel good the way I can" I demanded feeling a little jealous that she should let someone else, especially a boy, touch her the way we did each other. We were in bed together wearing only thin cotton nighties since it was summer and very hot. Susie rolled over onto me and I felt her hard little breasts press against mine and my nipples hardened, she kissed me tenderly and said, "My brother is very effeminate and sweet and gentle like a girl and he likes to kiss and tickle my pussy till I squirt my sweet juices onto his fingers!"
We were both excited now and quickly pulled our night dresses up, I spread my thighs so she could lie between them and fit her quivering pussy against my moist slit. Our clits were rigid and we both began to undulate our bottoms causing a passionate friction and tingling in our cunts. Her mouth was glued to mine and her tongue wriggled wildly over my teeth and lips and then deep into my throat.
I felt a familiar clenching in my stomach followed by sweet release and at the same time I heard Susie moan and felt a sprinkling of her cum on my bush. We had never orgasmed so hard and so fast before and we looked with surprise into each others eyes as our breathing slowed to normal. Then Susie began to giggle.
"I think the thought of my brother making love to me excites you as much as it does me!" she exclaimed.
I blushed and said, "I guess it does, but, tell me, do you let him fuck you too I do not think it could be nice – I mean a finger or two is fine, but a hard thick cock would be agony."
"Well," she said, "after he sucks me off, I put my hands on his stiffy and rub up and down till he shoots his gooey stuff all over his belly. It is sexy to see, and once it sprayed onto my tits and it felt all warm and tingly and made my pussy moist all over again. But no, we have never done more than that"
"Maybe next time he comes I will invite you over and then we can have him fondle you too. I bet you will enjoy it as much as I do."
"Okay," I said doubtfully and we left it like that.
A few days later I got a phone call from Susie, she was breathless with excitement and as soon as I said hello she said, "He's coming tomorrow! You must be here and stay the night, make any excuse you can think of."
"How about if I told my mom that we needed to finish a school science project" I asked.
"That's cool." Susie agreed, "See you tomorrow and remember to wear your sexiest lace panties," she added giggling happily.
The next day I went back to Susie's house with her after school. I was curious about her cousin and rather nervous too. Maybe I just did not like boys at all and Susie's brother would be no exception and I would not be able to hide my dislike and this could hurt Susie's feelings and that would be like, so very un-cool! Again, would Susie be jealous if I did like him and showed it I decided to be as tactful as I could and take my cues from her.
We got to Susie's house and waited impatiently for her brother to arrive. No one else was home and I was glad. I hid my nervousness as best I could but she was so excited about seeing her brother again that she did not notice that I was not as talkative and giggly as usual.
We had just finished drinking lemonade when we heard a car pull up and then he was there. I stared at him in amazement. I was looking at a mirror image of Susie except he was taller and had no breasts – the same face and gentle eyes, long eyelashes and smooth cheeks! A rather exciting, effeminate shy boy!
"Hi Sammy," Susie greeted him kissing him full on the lips.
"Meet my best friend Ruthie, she is going to stay the night here, I hope you don't mind," she said casually and from the look of surprise on his face I realized that he had not known about this and was now as nervous as I was!
"Didn't you tell him I was coming over" I squealed in amazement.
"Well, I like um, forgot," Susie said calmly and walked into the kitchen to get dinner ready.
We stood there not looking at each other and I could sense his embarrassment. He was so unlike the rough, brash boys in school that I felt somehow responsible for making him feel at home – even though it was more his house than mine.
"Why don't we sit down," I said cheerfully "and get to know each other"
He sat stiffly on the edge of a chair and I sank back on the sofa opposite. My short skirt rode up exposing my smooth thighs but he kept his eyes averted and gazed out the window at the garden beyond.
During dinner with Susie present he gradually began to relax and join in the conversation and seeing the easy familiarity between Susie and me, he was soon quite at ease and we three got along like a house on fire. We talked about school and music and then the conversation turned to boys and we began to tease him for being one of that insensitive, mean sex. He blushed and I saw his lower lip tremble in distress and I thought he was going to burst into tears. Impulsively I went over to him and hugged him to me and said:
"Of course we don't mean you when we talk about nasty, rough boys! You are very special and not at all like any of the boys at school."
Susie said, "Sammy, how could you think we would say nasty things about you I'm your sister and you are my cool big brother."
She then came over and hugged him even tighter than I had, pressing her breasts against his chest and then she kissed him full on the lips with a loud smacking noise!
I was now confidant that I could handle Sammy and I was eager to feel his "thing" and slide my hands on it and see him squirt. This was all new to me, I had always wondered what it would be like and now I was impatient to find out. To hurry things along I said I was tired and wanted to go to bed. Sammy said he would sleep downstairs on the couch but Susie just laughed and said:
"Don't be a silly goose, Ruthie is like my sister and anyway she knows we sleep together so why should you be uncomfortable on the couch"
Sammy looked doubtfully at me and when I smiled and nodded he said nothing more and in no time at all we had all three washed and brushed our teeth and were laying flat on our backs in the big bed comfortably wearing only our nighties. Susie was in the middle and she turned, gave me a mischievous grin and quickly rolled over Sammy so that he was now between us.
Before he could say a word she put her lips on his and began to kiss him passionately. One hand was holding his head to her while her free left hand pulled his nightie up well over his thighs. I sat up and got my first good look at the male organ. His penis was already beginning to stiffen under the expert tonguing he was getting from Susie and his nearly hairless little balls were wobbling excitedly. A faint musky smell dilated my nostrils and I felt moisture forming in my pussy. His shaft was growing thicker and harder before my eyes and I sat and watched fascinated by this thing with a life of its own.
I reached out and touched it tentatively then wrapped my fingers around it. His staff was slender and long and hard and fit snugly in my palm. It felt warm and smooth and unlike any finger of mine or Susie's. It was strangely arousing and even as I watched I felt a pulsing in my palm and the two balls pulled up sharply and thick white creamy cum shot up in the air and fell with a plop on his chest. This was followed with spurts of lesser intensity and the last few spasms coated my hand still holding his shaft. I fell back in amazement and gave a little shriek of alarm while Susie burst into peals of hysterical laughter. Sammy just lay there looking shamefaced his proud penis now softening fast.
"I guess the excitement of two girls playing with him was too much, he is usually able to control himself and do me with his fingers before I jerk him off," Susie said.
Sammy still lay on his back with his eyes closed and a sulky look on his face. As we talked and laughed over my experience I noticed two hot tears trickle from under his lovely long lashes and begin to roll down his cheeks.
Susie rolled her eyes and whispered to me, "He's so sensitive! But we can easily sooth him and have a lot more fun. Kissing him has made me very horny and I want to get him to 'do' me while you watch."
Sammy's tears made me feel very tender towards him and so I snuggled up to him and whispered that it was alright and he had done no harm and could we all go and clean up While I whispered I rubbed my soft tits against his arm and gently stroked his cheek. A smile came to his face and we all rose off the bed and tidied up.
We came back to the bed naked figuring it would be wiser not to mess our clothes up, seeing that Sammy was now feeling very comfortable with both of us. Susie immediately lay back on the bed and splayed her legs wide.
"Come on big bro' I want you to eat me out while Ruthie here sits on my face! We have never done that before and I am sure we will all love it."
Sammy obediently moved between her legs and grasped both ankles to hold her legs wide, he then lower his face and let his long tongue lick the swollen pink gash. Susie moaned and then I was astride her head lowering my dripping pussy to her lips muffling all further sounds of pleasure from her.
I sat on her facing looking down at Sammy bent over licking Susie's gash. Her hands came up and her thumbs held my lips open wide so that her tongue could go deep into me. I had never felt so open and loved the feel of her nubile tongue in places we never normally reached. I grabbed my tits and squeezed them, the sensations were electric and I felt myself go over the edge gushing sweet juice onto Susie's eager lips.
Susie was too excited to last long, her brother had 2 fingers sliding in and out of her wet pussy and his lips were sucking hard on her exposed erect clit. No sooner had I cum than she too gave a muffled moan and sprayed Sammy's face with her juices. We both flopped over breathing hard and lay with our eyes closed enjoying the after glow of a satisfying climax.
We both opened our eyes at the same time to see Sammy standing at the edge of the bed looking down at our naked bodies and stroking a hard erection between his legs.
Susie jumped up with a yell, "stop Sammy, you must use that to fuck me with, now is a good time as any to do it!" but much to my surprise Sammy shook his head, "No sis I can't do that, it does not seem right some how."
Susie was silent for a moment as she digested this illogical remark but being a resourceful young lady she turned to me and said:
"OK big bro' why don't you fuck my friend Ruthie then I bet she is dieing to try it out, aren't you Ruthie"
It had not occurred to me that we would go beyond heavy petting and licking and sucking and now here was my chance to experience what real penetration by a hard cock would be like.
"Well, I don't know," I said hesitantly but Susie just jumped up and pushed me down on my back and pushed my thighs apart. I must confess I was aroused and curious to know how it would feel to have a cock go into me instead of a pair of smooth fingers, so I did not protest but lay back passively.
Susie grabbed Sammy's hard on and pulled him up to the bed and then got behind him and pushed him on to me. He lay awkwardly on top pressing my tits flat and stifling me with his weight and his hard cock pulsing gently near my belly button.
"Get your weight of her you silly boy," yelled Susie pulling up on his shoulders and I began to breath again. Now his stiffy was quite out of position and I felt it slip and slide over my belly and thighs. He went on jerking around while I just lay there with my eyes closed and Susie looked on in astonishment. Then she stepped up and grasped his cock and tried to bend it down to align with my pussy.
Sammy gave a yelp of pain and jumped off me.
"Hell Susie that hurt! I thought that you just got to get on top of a girl and it goes right in!" moaned Sammy and I could hear the frustration in his voice. I looked inquiringly at Susie who was sitting back on her heels with a puzzled look on her face.
"Something is not right she said thoughtfully, let me think."
"I know," she said breaking into a smile, "remember all the pictures we've seen of people fucking The girl always has her legs up in the air! That's what's wrong, Ruthie you have to lift your legs up and then I bet Sammy's cock will just slide in! Come on lets give it a try."
I lay back down and opened my legs wide and then pulled my knees up to my chest. As I did so my pussy swung up into view and Susie gurgled with delight and screamed for Sammy to get back into position. With a clear view of his target Sammy lowered himself down and I felt the head of his cock touching the puffy petals of my aroused pussy. I closed my eyes tight and held my legs up with my hands, the hard rubbery thing pushing at my pussy lips began to go in past my outer lips and into the wet opening beyond. I felt a stretching of my lips and then a ridged knobbly something was moving up into me. The walls of my pussy felt stretched and pleasurably painful and above me Sammy sighed at the sensations my tight pussy was giving him.
I had never experienced any thing like this before. The difference between smooth fingers and an erect knobby cock inside me was like day and night. I moaned and heard an excited Susie say, "is it good Huh! Does it feel nice OhmiGosh! He's right inside you!"
I just lay there with my eyes closed rocking my head from side to side as waves of pleasure washed over me.
"Move in and out of her," Susie screamed excitedly seeing the aroused look on my face. She knew I was very turned on and close to orgasm. I felt his piston shunt in and out a few times and then my pussy clenched, my thighs shook and my nipples seemed to explode. I think I let out a hoarse cry of joy before I went limp and let go of my legs.
He was well mounted now and right up me holding on tight and the convulsions of my pussy as I came threw him over the edge and he discharged gob after gob of warm cream far up my belly. The soothing jets were like balm to my excited insides and added an extra pleasure to fucking as opposed to masturbation. I opened my eyes and looked up at Sammy looking down at me with adoring eyes. We had given each other a fantastic experience and we both knew it. Susie sensed it too and brought us to our senses when she said:
"Sammy that was quite something and you must promise to do it to me too. I want to experience what Ruthie did and, Ruthie, you must stay and watch because that makes it more fun for us."
"Okay, said Sammy with a smile, I can't wait to do it with you too. Thanks sis for teaching me how to fuck, I guess I owe you one!"
And he was right.
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- Story Details and Information
- My First Boyfriend
- Published: Sep 13, 2004
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- Category: First time sex story
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