My Brother's Girlfriend

by

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

Desc: 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.

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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.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Consensual / First / Oral Sex / Voyeurism /