My Brother's Girlfriend

by G Younger

Copyright© 2015 by G Younger

Romantic Sex Story: My Brother's Girlfriend is a story of twin brothers and the quest of one of them to lose their virginity. His girlfriend hosts a Halloween Party with the hope they will finally hook up. He asks his more experienced brother to watch him and give him pointers. How could that go wrong? 2015 3rd Place in Halloween Contest.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   First   Oral Sex   Voyeurism   .


Chapter 1

My little brother had always come to me when he had a problem. Our parents had divorced when we were ten. We were identical twins, but I was fifteen minutes older. Our dad then cheated on our mom, and got his secretary pregnant. Shortly thereafter, our parent's divorced, and he married the bimbo. That was the last we saw of him except when he needed to trot us out for some event or large family function. He was a family man, after all.

Mom didn't take it well and went into a deep depression that lasted about three years. This had left me with the job of taking care of my little brother. I know, we were the same age, but he looked up to me. Lee had been a good kid, if a little shy when he was younger; but he started to come out of his shell when I introduced him to sports. By the time we reached high school he was considered a jock.

In a lot of ways my little brother was still a little kid. I had been the one who had been forced to grow up and take charge. I protected my brother from the world, because he had always been so trusting and innocent. I worried what would happen if we ever separated, and someone took advantage of him. It wasn't that he was stupid or anything. He was one of the brightest guys I knew, but he wasn't street smart.

So it wasn't surprising when he came to me to ask for some advice. "Are your busy?" Lee asked.

I was surfing the net in my bedroom and looked up from my tablet. "Not really, what's up?"

Lee looked nervous and just stood in the door way. I could tell that something was really bothering him. I figured I had better help him out. "Come in and shut the door."

He hesitated, but whatever it was he decided he needed his big brother's help. He walked in and shut the door behind him and went over to my bed and sat on the edge.

"Okay, you know you can tell me anything, so what's wrong?" I asked.

Lee hesitated and then let out a long breath.

"Tonight is the party at Mona's..."

Mona and Lee had been friends since they were little. Even though my little brother was out of high school I doubted he had ever even kissed a girl. It wasn't that he wasn't interested; it just didn't seem to be in him. He could be aggressive on a sports field, but get him around a girl and he was completely lost. Mona, being a Tom Boy, hadn't seemed to set off his usual panic button, when she took notice of him. I wasn't completely sure if Mona wasn't more interested in the other team, if you know what I mean. When they had started to date, it took everyone by surprise. Mona had asked my brother to the Valentine's Day Dance last year. That was six months ago, and their relationship was still very G-rated. Holding hands was as far as they had gone. I was suspicious that Mona was just using my little brother as cover for her true sexual leanings, but I loved Lee and she seemed to make him happy. Trust me, Mom and I were just happy he was dating a girl. They were both eighteen now, and I wondered if this was supposed to be a date party. The last party Mona had was just for girls. Lee didn't take it well that he hadn't been invited.

I remembered my first boy-girl party. It had been at Stacy Thompson's house and there was a make-out room set up in their den. To know then what I know now, at my first make-out party ... I could see where Lee would want some advice. It felt weird talking to my brother about this type of thing. I mean for Christ's sake, there was the internet! Surely he had surfed the net, and found out how things worked. I had always been the adventurous one. I had lost my virginity at the age of fourteen.

Lee and I may have been twins, but we didn't really run in the same circles. So it wasn't uncommon for us to be invited to different things. The thing was though, that if we wanted, we could switch and fool just about everyone, but our mom. There were times we played the switch for fun.

We had switched at graduation and the parties that followed. I had laughed my ass off when my little brother had come stumbling home drunk off his ass. I would bet it was the first time he had ever gotten drunk. I had a fun night playing laser tag with my brother's geeky friends.

As the silence hung in the room I gently nudged my brother by saying, "And?"

It all came out in a rush.

"It's going to be a couple's party and I think Mona wants me to make out with her. I'm not really sure what I'm supposed to do. We have never even kissed, and I'm sure Mona is going to expect me to do that."

"Can I tell you a secret, Bro?" He looked up at me expectantly. "Mona has just as much experience as you do, so there is no reason to be nervous. Let me give you some advice that has always served me well. Take your time, and make sure she is comfortable with what is happening. A willing partner is always better than a wrestling partner.

"Afterwards, never kiss and tell. If you ever expect to go out with her again, or have any other girl want to go out with you, they have to feel safe with you. That includes protecting their honor."

My brother gave me a look like I had two heads.

"Sure ... What I was hoping was that you could watch us and give me tips."

It was my turn to look at him as if he had two heads.

"What the fuck are you talking about?" I asked.

"Mona and I have our computers linked with our webcams. You could watch the webcam and then when I get home give me tips on how to do it better."

That was the last thing I had expected him to say. I really had no desire to watch my brother and his girlfriend make out.

"I don't know, Bro. Mom wanted me to help hand out candy, and then I planned to go out tonight. It is Halloween, after all."

My brother looked crestfallen. The one thing I could not fight was when he gave me that hangdog look with his big sad brown eyes. There was too much history to leave him hanging. I was between girlfriends and it was just going to be a guy's night out. My best friend Curt and I could go out some other time, or go out later tonight.

"I guess I could..." I said after a moment's thought.

He immediately perked up and jumped up and hugged me.

"You're the best!"

I had serious doubts about if this was a good idea or not, but he was definitely the only one that could ask me to do something like this and get me to agree. He left the room with a bounce in his step.

My mom thought it would be cute if we wore the same costume. My brother and I put up with it because it seemed important to her. This year we were going as vampires. We had black pants, a white shirt, and a cape with a hood that Mom had made. It was red silk on the inside and black on the outside. Lee had found some fake blood and he made me put it on my lip and made it look like I had just bitten someone. It had been years since I had dressed up for Halloween, but my mom and Lee really were excited, so I didn't put up a fight.

My brother had left the house and been gone for about a half hour when I got a text to turn on the webcam. I had just scared a group of ten-year-olds. I guess our getups were believable! I grabbed my tablet and turned on the video chat.

"Hey, Bro, you there?" Lee asked.

I turned on the webcam video on my side so he could see me.

"I'm here, and all ready to be a perv."

Lee gave me a look and said, "Can you see the bed okay?"

I looked at the image on the screen and I could see pretty much the whole room.

"Everything looks fine on this end. I will sign off now so she can't see or hear me. Good luck tonight."

Lee gave me one of his quirky smiles.

"Thanks, man, I really appreciate this."

I don't know how long it was because I had dozed off in the easy chair. We hadn't had any more trick-or-treaters for a while. Mom had gone off to bed. She had an early morning at work, so I was left in charge of any stragglers. I woke as I heard Mona enter her room. She was with one of her friends, Lisa. Mona had a toga on and Lisa wore a princess outfit.

"Jeff is such a dork, sometimes. If he would just grow up and treat me like his girlfriend, instead of his best friend, things would be so much better," Lisa whined.

"I know ... Lee is the same way. He is such a little boy. If he even had half a clue as to what he was doing, I would have gone all the way with him tonight. Instead they are horsing around playing pool," Mona complained.

I had never really paid much attention to Mona since I wasn't sure if she was into guys. She had always just been the kid who hung out with my brother. I noticed she had turned into a hot little number. She had always been lean, and her nice legs were shown off by her short dress that showed what a nice tight butt she had. She sported the swells of breasts that held some promise. The sheer fabric of the toga showed a hint of her nipples. She was definitely not wearing a bra.

My brother was an idiot. I picked up my phone and texted him to get upstairs.

"We need to find someone to lose our virginity to," Mona reasoned.

"But who would do it and keep their mouth shut about it?"

Mona looked serious a moment.

"Lee's brother..."

I had just taken a swig on my soda and I promptly shot it out of my nose. Over my coughing I tried to listen to Lisa's response.

"But he is so out of our league. I know he and Lee are brothers, but he has girls lined up to go out with him. There is no way he would give either one of us the time of day."

"I heard that Gina Wilson said he is great in bed."

Mona had Lisa's attention. Lisa got a nervous look.

"Wouldn't you be scared he would just use you and then never call you again?" Lisa asked.

Mona got a faraway look and then laughed.

"I would be willing to risk it. Gina said she had never cum so hard in all her life."

Gina still flirted with me, but we would never be more than friends. I needed to call her and see if we could be friends with benefits. We had always had great sex, but that was all we were great at.

"I hear that!" Lisa exclaimed, bringing me back to their conversation.

There was a knock at the door. Lisa and Mona looked at each other like they had been caught doing something.

"Who is it?" Mona asked.


"Come in."

Lisa left as Lee came in and put her fingers to her ear and mouthed 'Call me'.

Lee looked deep into her innocent eyes. She was just the right mixture of innocent and playful. If she had not been going out with my brother I would have been all over her, if she had looked at me like she was looking at him. Her hot little body, which was coming into womanhood, just screamed FUCK ME!

Mona got a serious look on her face.

"I thought you weren't interested in me?"

Lee stepped close to her and cupped her chin so that she looked up into his eyes.

"You are gorgeous, and we have been friends too long for you to doubt my interest in you. Plus you're smart, funny and talented. There is no one I would rather be with right now."

I had to give my little brother kudos for making the save.

He then leaned down and kissed her on the forehead. I could see her tense up for a moment and then she relaxed as she stood up and pressed her body into him as she gave him a hug of appreciation.

Lee and I had been working out and I could see his toned body engulf her small frame in a bear hug. In my mind's eye I could imagine her body pressed against me and I felt my desire to possess her. She pulled back a little and looked down at the bulge that had obviously been pressed into her. She placed her hand on his chest and broke their embrace.

Lee got a look like he had made a huge mistake.

"Mona, I am sorry. I don't want to do anything that makes you feel uncomfortable in any way. If I do something wrong let me know, and I will respect your wishes."

I had to give him high marks for listening to me.

She got a thoughtful look on her face. As an answer she started to untie her toga. Her hands trembled, and she was having trouble getting it undone. I was sure my brother would shit himself by the look on his face. He had an expression like he was on the verge of either running out of the room to keep from her from ravishing him; or throwing her on the bed and have his way with her. I voted for him to throw her on the bed.

She was so damn hot. I just wanted to crawl through the monitor fuck her 'till she could no longer walk. When she had reached for the knot my dick had gone instantly hard. I could see her hands quiver and Lee reached over and placed his hand over hers. She looked into his eyes and I could see the disappointment of him stopping her.

"Let me," Lee offered

Her arms dropped to her side as my brother began to untie the toga. He let it fall open exposing her pert upturned breasts as it bunched around her waist. They were every young man's dream. They were round and upturned and her nipples were getting hard. They looked like a perfect mouthful.

Lee took his large hands and ran them over her stomach and around to her sides. He then slid them up her sides caressing her. I wondered when he had grown a pair and taken control of his fears.

I could see Mona shudder, and goose bumps appeared up and down her body. I could tell she had never taken her shirt off for a guy, but she let Lee control her body.

Her nipples had gotten harder and extended. Lee then turned her around so that she faced the webcam, exposing her nude torso to me. He reached around her waist and placed one hand on her stomach and took the other to pull her hair away from her neck. She titled her head and he bent into her and his lips lightly brushed her neck.

Lee kissed her neck and worked his way up to nibble on her ear. The erotic nature of his caresses had caused her nipples to come to full attention. He reached up and took both her breasts into his hands. He rubbed his palm against her nipples making them rock hard. Mona moaned with pleasure. This was the most erotic thing I had ever watched. My little brother must have watched a lot of porn to be pulling off these moves.

Lee took his left hand and slid it over to her right breast and slid his other hand down her side toward her waist. He reached down and hooked his thumb in the waist band and Mona wiggled her ass so that her toga fell down her legs and bunched around her ankles as she stepped out of it.

Lee pulled her body back against his, as he ground his crotch into her teen ass. His hands ran up her stomach and landed on each breast again. He kneaded her breasts, and then pinched her nipples and she had a shocked look of ecstasy. Mona leaned her head back and twisted her body so that she faced him.

"Kiss me," she begged.

Lee bent down and kissed her. She was very passionate and obviously fed him her tongue. He broke the kiss and pulled his shirt over his head.

I was busy admiring Mona's form. She had a hot little hard-body, with the perfect heart shaped ass that only teen girls seemed to have. He stepped forward and pulled her panties down and exposed her hidden treasures. Mona had a tuft of black hair just above her swelling pussy.

Before she knew what to say or do, Lee swept in for the kill. His mouth brushed against her, his tongue demanded entrance into her mouth. Her hands came up as if to defend against him, but instead melted against his chest and slid up to encircled his neck, and willed him onward.

Lee kissed her passionately as his fingers caressed her flat stomach and he slid them down her side to cup her delicate ass. He pulled her tight against his body. His face got very red and he groaned. He pushed her away and you could see the telltale wet spot. My brother had just cum in his pants.

"I'm so sorry," he muttered.

"What's wrong?" Mona asked.

Lee grabbed his shirt and pulled it over his head. He grabbed his cape and all he could do was whimper as he teared up and ran from the room.

Mona was left naked and aroused with a confused look on her face. My dumb-ass brother had fucked up, big time. I could see Mona start to cry. I turned off my tablet. It broke my heart to see her so upset. I worried if my brother would ever be with a girl after his performance tonight.

Lee called me about an hour later and said he would stay the night at Jeff's house. He said that if Mona called to not tell her where he was right now. I agreed. I did not mention anything I saw. In years to come Lee and I would never talk of what happened this night.

Chapter 2

I had always been the one to fix things for my little brother. I decided to go over to Mona's, and help explain why she shouldn't give up on the dork. I figured a quick conversation and then I was off to a party with the guys. I walked up to the door and it looked like Mona's party had broken up. I knocked and a very pissed off girl met me

"What do you want?" Mona demanded.

"Ahh ... I thought it might help if we talked," I suggested.

She began to shake, and I could see the tears roll down her check. I reached out and took her hand and stepped into her house so we weren't making a scene on the front steps. She grasped me in a bear hug and began to sob. All I could do was hold her and let her cry it out.

I quickly realized that I had a raging hard on. I had just seen this cute girl, my brother's girlfriend, naked a short time ago, and now I had her pressed up against me. She was like a drug that I was addicted to. I had to have her. My normal self-control over my sexual being had slipped away the instant she had pulled me into her arms. I said her name. She looked up to me and I leaned down and our lips touched. I knew this was wrong, but I was now a slave to my lust. I knew that if I allowed this to continue that it could have dire repercussions, but at that moment ... I didn't care.

It was as if all her pent up tension evaporated. She slid her hand behind my head and pulled me into a passionate kiss. She pushed her tongue into my mouth and it was obvious this was not a friendly peck from a brother's girlfriend.

I don't really know what she thought when I led her to her bedroom and closed the door behind us. But when I turned around and found her eyes glued to the bulge in my pants, I figured she knew the score. As I walked to her I undid my pants and dropped both my pants and underwear letting her get a full view of what was about to buried in her virgin twat.

My boner had her mesmerized. I reached out and she offered no resistance as I untied her toga exposing her perfect little breasts. I didn't slow down as I pushed it over her hips. She hadn't bothered to put her panties back on. Mona stood before me in all her glory.

I leaned into her and our tongues danced playfully around each other as her hands rose to grab the back of my head. My fingers trailed around her sides and up to cup her breasts. Her nipples were very sensitive and my caresses were sending her arousal level up every time I kneaded her tender flesh. I felt Mona whimper in my mouth as I toyed with her nipples. I winced as the throbbing of my fierce erection grew nearly unbearable.

Mona broke away, panted loudly, and her chest heaved as she tried to catch her breath. She looked into my eyes again, and for one endless heartbeat both of us stopped breathing. I could see her make a decision as she reached down and grabbed my dick. I stiffened and arched my back as she stroked my member. She was emboldened by my response as she knelt down in front of me

My dick hit her in the forehead. It left a glistening streak of pre-cum where it had grazed her. She could not get her fingers to completely circle the circumference of my pole. I had never seen it get this big. She shuddered. I could only imagine her thought of what would happen as my cock ripped into her.

She took both hands and grabbed my dick at the base and did short little strokes as she worked her way up until her hands were wrapped just under the sensitive head of my dick. I almost busted my nut right then and there. Mona seemed to be fascinated with my dick. It jerked around as if it had a life of its own.

I pulled her up and backed her towards the bed, and when her legs touched the edge I had her sit. I took off my cape and shirt, and stood before her naked. She had released my cock when she sat down, so it was bouncing up and down right at her mouth level. I hesitated, because I wanted to jam it down her throat, but I decided on another course of action. I took my large palm and pushed her chest back so that she laid lay back as with her legs hanging off the bed. I dropped to my knees and grabbed an ankle in each hand and lifted her legs so that they were now hung over my shoulders.

Mona tensed.

"Are you ... ohhh, God," she moaned as my tongue flicked out and landed at the top of her pink slit.

With slow even pressure I burrowed my tongue deep into her small inner labia. I circled slightly up and found the small hard nub of her clit. I worked my tongue around it again and again, only grazing over the little nub once. Mona growled and her thighs tried to press together, but I held them open as I continued to work my magic.

"Fuck, crap, shit, mmmmm!" Mona moaned as I attacked the center of her womanhood.

Her hands grasped the back of my head and pulled me hard into her gash. Her head tossed back toward the headboard and her back arched. I was giving her virgin twat pleasure beyond anything she even dreamed of. I sucked her swelling lips into my mouth and lightly chewed on them. Mona acted like she was going to go out of her mind.

I withdrew my tongue, and raised my head just slightly enough so that my tongue pulled off her clit.

"Huh, don't stop!" Mona mewed.

She glanced down and saw me stare up at her through the valley between her baseball-sized breasts, and I grinned broadly. She giggled nervously.

Slowly I brought my fingers over from her thigh and pressed them up against her moist velvety folds. My fingers spread her pink pussy lips apart. I gazed down upon the small, unquestionably tight entrance to her love canal and sighed contentedly. My middle finger traced the rim of her opening and slowly pushed inside.

Her pussy was soaked and easily allowed my digit access, and almost seemed to suck it further inside.

"Oh God!" Mona cried, hair flying around her head as it shook in a pleasured frenzy. "Yes!"

I sank my finger in until I felt the resistance of her hymen. The girth of my finger totally stretched her. I wondered if she could ever handle my dick.

"Relax; I am going to get you ready for later."

I pressed and her hymen stretched and then she tensed as I broke her cherry. She stiffened in momentary pain but her passion soon overcame her.

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