Oh Brother!

We rolled onto our sides which made it easier. I sucked on the head of his cock, then licked down the shaft to his balls. I sucked on his balls for a bit while stroking his cock with my left hand. Then I licked him up the shaft again to the head and sucked again. I tried to concentrate on making him feel good. His mouth was working wonders on me and in a matter of minutes, I came in Doug's mouth. He swallowed it all. I sucked harder and Doug thrust his cock into my throat. He held my head as he face fucked me until he blew his load down my throat. I gagged a bit and he pulled out. His cum was dripping all down my chin. I licked it all up and swallowed it.

My date with Pauline was nothing special but we did make out. I was enjoying it but Pauline stopped me after a few minutes. Later she told me it was nothing personal but she thought I kissed like a girl. That night Doug asked me about my date. I told him the truth. He asked, "Did she blow you or give you a handy at least or a dry hump?"

I shook my head. "No, nothing else happened. What about you and Joan?" I asked.

Doug snickered. "She licked my cock for a bit but wouldn't put in her mouth. She jerked me off after but wouldn't eat my cum either. I had to towel it off," he claimed. Later that night he came over to my bed again and without saying a word, dropped his pajama bottoms and pushed his cock into my face. He was already hard. I opened my mouth and blew him as quietly as I could. After he dumped his load into my mouth, he snuck back to his bed and went to sleep. I masturbated for a while after until I came too.

That set up numerous other occasions when Doug would make me suck him off. If I needed a ride somewhere or he did me a favour, I had to pay the price. Sometimes if he went out with a girl and she didn't satisfy him completely, he would come home and get me to blow him. There were times when I would ask for another kissing lesson. I really enjoyed making out and not many girls were doing that with me. Doug would act like he was doing me a huge favour and would make out with me but only if I promised to suck him off after. I always did.

Then there was that day. Our brother David had already finished school and moved out. He got a job at the same factory as my Dad. He was also engaged to his girlfriend. With just Doug and I in the basement, we would often sleep together in the same bed. We would read Penthouse, whisper, sometimes kiss. Sometimes we would suck each other off. More often we would just masturbate. I would roll on my side and hump my sheets and Doug would jerk off behind my back. It was summer and very hot. We didn't own air conditioning. Doug suggested sleeping nude.

When he crawled into my bed behind me, I could already feel his hard on touching my ass. He started telling me a story and drew pictures on my back with his finger. Then he was kissing the back of my neck. He pushed my long blonde hair aside and kissed my neck passionately. It was a turn on and I wanted to roll over and make out. Instead he forced me to stay still and tease me. He kept grinding his cock on my bare ass cheek. He was telling me a story about fucking a girl doggy style and then sliding out of her pussy and putting it into her ass. I was excited by it all and was grinding my hard cock into my balled up sheets. My hip gyrating was really turning on Doug. I asked him, "Do you want me to suck you off Doug?"

He didn't say anything at first and just kept rubbing his cock on my ass cheek. "Hey Marty? Don't you want to loose your virginity?" he asked coyly. I knew that he had been with several girls by then but I had not gone all the way with anyone. I was so naïve that I lost his meaning.

"Of course I do, I'm way over due," I responded. He placed a big kiss on my neck and slid his cock into the valley between my ass cheeks. He continued pumping and his cock grazed the surface of my asshole.

"You know about anal sex right?" he asked as he spit into his hand and rubbed the saliva all over his cock and between my ass cheeks. I suddenly began to panic. It was too much. I was afraid.

"No Doug, wait" I snapped. I turned on my hip and his cock slipped out of the crease. "No, I can't. It's too far Doug. We have to stop," I pleaded. Doug bit into my shoulder in frustration. I said, "Just let me finish you with my mouth."

He definitely had his mind elsewhere though. "Marty, don't worry, I'm not going to hurt you. I'm going to be gentle. I know you want to do it. You have such a beautiful, sexy ass. It's made for getting fucked," he pleaded.

I held my ground. "No Doug, you're not going to fuck me," I said. I was reaching for my pajama bottoms to put back on.

Doug put his arm on me. "Wait Marty, wait. You didn't think I was going to put it inside you did you? I won't do that to you. I was really enjoying fucking the crack of your butt like that. It was hot. You didn't mind that right?" he negotiated.

Truthfully, it had been nice up until that point. I dropped my bottoms again. "Just the crease, right?" I asked.

"Yes, that's all," Doug promised as he got excited again. He lowered his face down to my bare ass and gave each cheek a gentle kiss. I eased up. He then spread my cheeks apart and spit a big, hot dollop of saliva right onto my asshole. He then spooned me again and placed his cock back into the crease. He slowly and gently began humping me again. It felt very nice and I soon had a hard on of my own again. Doug reached around me and took hold of it and began pumping it with his palm. He asked me to move my hips again. I loosened up and began humping back at him. It was nice again and Doug resumed kissing my neck.

It was all nice like that, Doug giving me a hand job while he slid his saliva coated cock between my buns. Both our hips were gyrating. I felt like I was close to coming. Doug was thrusting harder too and I knew he would soon blast a load on my back. As pre-cum oozed from my cock into Doug's fist, he shifted his hips a bit and I felt by asshole begin to split open. I wasn't sure if it was intentional or an accident so I tried to twist away. Doug used his superior strength to hold me in place though and pushed his cock into my virgin ass.

"Ow Doug, stop! You're inside my asshole," I pleaded. He just pushed in deeper. The pain was torture. My eyes watered. "Ouch Doug stop! It really hurts," I pleaded half crying. Doug stopped moving but his cock was already most of the way up my bum.

"It's okay, shh! The pain will go away in a minute. You just have to relax and breath deep. I won't move but you have to let your butt muscle adjust," he whispered.

I struggled, "No Doug, pull it out. I don't want to get fucked." I squirmed but Doug was much stronger than me.

"Shhh, easy now. Just relax and breath. You'll thank me after," he insisted. I couldn't struggle away so I tried to calm down and continued to cry. I took some long slow breaths. The pain began to sting less and started to feel like a dull pain. Then I felt the pressure increase some more and could feel Doug's balls pressing against mine. Then he slowly drew back almost all the way. I thought he might take mercy on me and pull out but he waited with the just the tip in my butt for a minute before plunging back in. It hurt again but not as bad as the first thrust. He slid back out again and then back in, increasing his tempo until he had a fucking rhythm going. It really burned and I was crying the whole time but I gave up struggling and submitted to getting fucked. When Doug felt me give up the fight, he took hold of my hips and really fucked me.

It became a dull sensation as he ploughed my asshole mercilessly. After five minutes of fucking me like that he rolled me onto my front without removing his cock from me. He grabbed my hips and resumed fucking my ass doggie style. He built up speed until I went completely limp and let him fuck me without resistance. My cock wasn't limp though and when Doug reached around and gripped it again, I went off in his hand immediately. He began laughing and ploughed me real hard a couple of times as he exploded inside my rectum. He slowly pulled out and my asshole was left gaping as his seed dribbled out of me.

Doug kissed my cheek and whispered, "See, I told you that you would like it." I was sobbing into my pillow.

I rolled onto my back and said, "Fuck off Doug. You're a rapist. You had your fun, now get the fuck out of my bed and you're never coming back to it again." I kicked him in the shin and grabbed my bottoms. I pulled them on and covered myself with the sheet. Doug took the hint and went back to his own bed.

At that point in the story, the Doctor Carter stopped me and asked if I needed a break. She was the first person I had ever confessed that too. "So that was it between you and Doug then?"

I went on, " Not exactly." Shortly there after, Doug got his girlfriend pregnant. He had to drop out of school to get a job working full time to take care of his new wife and the baby. My parents and Susan's parents both insisted that they get married. Doug worked in a restaurant as a dish washer. He was able to afford a cheap one bedroom apartment for his new family.

Doug and I didn't have anything to do with each other for a while. I finished high school with honours but my parents didn't have any money set aside for college so I joined the Air Force and went to their academy. I tried all three services but the Army laughed me out the door and the Navy never got back to me. I was still slim and effeminate. The Air Force didn't seem to care so I spent fours years in their school, got a degree and was assigned to a radar station. It was my first year there at the Academy when I finally lost my virginity to a woman. About half the candidates were female and we all drank a lot. Drunken hookups happened all the time. By the time I was done school, I had been with four different women. There were also two different guys who must have sensed that I was bisexual. Although same sex relations were still forbidden at the time, I did have a few discreet encounters with those guys.

My posting wasn't much fun however. The job was very boring but I was locked in for four years. I did have a girlfriend for a while which lasted almost a year. When I told her that I was getting out at the end of my term she wanted to know what I was going to do after. I honestly had no clue. That was enough to get me dumped.

During all that time, I still got to see the family from time to time. Christmas and Thanksgiving were every year. There were also birthdays, babies, weddings and funerals. My brother David was still married and his wife was pregnant with number five. Janine married her high school sweetheart too and had three kids of her own.

Doug had got a divorce from his first wife after three years together when she discovered he was fooling around on her. Doug had worked his way up at the restaurant. They made him a cook after only a few months. Two years in, he was a souse chef. A year later he was their top chef. He wrote the menus, shopped for the produce and meat, directed the kitchen staff and made himself invaluable. He was boning a couple of the waitresses and failed to keep it hidden from his first wife. That's why they got divorced. One of those waitresses got knocked up and Doug, with pressure from Dad and Tracy, married her too. They ended up having two kids as well.

That lasted until the restaurant got so popular that they wanted to expand. Doug was put in charge of starting up the new location. He hired the contractors, oversaw construction, micromanaged every detail and hired the staff. All the servers he hired where hot looking girls. It wasn't long before he was boning most of them. Again his wife found out and left him. It didn't seem to phase him. He helped the company expand and became their general manager. Nine years after dropping out of high school he was more successful than any of us.

I really only saw my siblings on family occasions generally. I had so little in common with any of them. I got an entry level job as an engineer for a cable television company. My eight years in the Air Force had made me a stronger person and confident. I was physically in shape although I still had a slightly girlish figure. My shoulders were narrow and my bum was round. I had thick, pouty lips, small arms and the same white blonde hair. I started growing it out again as soon as I left the service.

I still had a tough time meeting women. I dated the girl who worked at the video store for a while but it didn't last. There was another lady from my gym that I dated a few times but she dumped me for some steroid freak. I tried the bars but never got anything but drunk. I was so jealous of my brother Doug who didn't have to do anything. Women just threw themselves at him.

I made a habit of going to an adult store that was just a few blocks from my apartment building. I started with just buying Penthouse magazines but then moved on to other magazines. I found some good kinky ones with all forms of bisexual entanglements. The girls that worked there got used to seeing me and knew about my preferences. Once I felt comfortable shopping in there, I expanded to buying sex toys and lingerie.

The lingerie was an impulsive purchase as I had no girlfriends at the time. I found myself trying the items on at home and the satin and lace under garments were so much sexier than my boring male underwear. The sex toys fascinated me too. At first I bought a pocket pussy but found my old way of masturbating better. Then I had to have a realistic dildo. It just called to me. At first I just sucked on it while watching porn or was masturbating in bed. Then I had the urge to fuck myself with it. It took a few weeks of practice and lots of lube before I could take it comfortably. Then I bought a butt plug so I could leave it in to stretch my asshole.

One day when I was in the adult store, the girl handed me a flyer on my way out. It was a promotion for a gay night club. I almost threw it away but held onto it for a some reason. I didn't feel like I was gay so the thought of going to a gay nightclub scared me. Afterwards, I thought, since I wasn't having much luck with women, I might give it a try. It had been a few years since I had been with a man.

I dressed in a casual suit when I went to the club. I was nervous and shy and didn't know anyone there except the girl from the adult store who was with her girlfriend. I drank and danced a little but didn't have any better luck than I did at the straight bars. I was fascinated by the transvestites though. Some were over the top drag queens with way too much makeup, outrageous wigs and flamboyant outfits. There were a few however that were just trying to look like women. Most were not very convincing as they were too manly built or couldn't walk in high heels. There was one boy who looked really good wearing just a simple skirt and blouse, light makeup and an auburn wig. His figure was not far from mine, a bit skinnier but not by much. It did get me thinking though. I wanted to go talk to that transvestite but she was very popular with the crowd I could not get near her.

I didn't go back there for a while. I spent most of my weekends in, watching television or porn. After a while I became very comfortable using the dildo on myself until it became habitual. I ended up buying a bigger one. I often thought about that day that Doug raped me. As much as I tried to put it out of my head, I couldn't. Sometimes I found myself masturbating with the dildo up my ass while thinking about that event. I obsessed over it. I started calling out Doug's name when I came. That was when I knew I had to talk to him.

One night I made my way to his restaurant. He was working, running around like a chicken with his head cut off. When he saw me, he got me a table and told me to order whatever I wanted. It was on him. He then went back to barking orders at the staff. The food was good and the waitresses were all smoking hot. I ate alone and after a while it slowed down enough for Doug to come sit with me. He brought us over each a scotch on the rocks. "How was the food?" he asked with his familiar boyish grin.

"Real good, excellent actually. Thank you Doug," I replied. He shrugged it off like it was nothing. When the waitress came to clear my plates, she eyed Doug like a groupie at a concert. Doug smacked her mini skirt covered ass as she turned away. She just blushed and slinked away. I thought that if I tried anything like that at work I would be fired within minutes after getting decked by the recipient. I looked at Doug, "Are you fucking her?"

Doug giggled and nodded. A different girl walked by, equally as stunning as the first and she bit her lip as she passed us while staring at Doug. I don't even think she saw me. Doug winked back. I was in awe. "Her too? How many of these waitresses are you fucking?" I asked.

Very casually, Doug replied, "All of them." As he drained his scotch and signaled for another, he asked me why I was visiting him at work.

"I thought that it has been too long since we could really talk. Growing up you and I were very close. I miss those times. You hurt me and I was mad at you. I think it is time to forgive you and move on. I don't know how you feel about us but I'm here if you ever want to talk about it," I stately plainly. It felt good to get that off my chest.

Our next round of scotch arrived and Doug drank his quickly. He smiled at me and giggled like he did. "Okay. You forgive me, that's great. So what's that mean? You want to hang out now? You want to suck my cock again? I don't know what you want," he replied. Life had hardened him but it had hardened me too.

"You and I shared something Doug. We had something good. If that's what you want then sure. I can suck you off, whatever. I just want us to be bothers again," I said as I reached over and touched his hand. Doug ordered more drinks for us then got up to do more work.

"Why don't you hang around? Don't worry about your bill. It's on me, just tip the waitress," he said. I sat and drank for a while and observed the atmosphere. When things slowed down, Doug finally returned to me and invited me for a tour of the place. As he showed me the kitchen and back rooms, he introduced me to his staff as his brother. Everybody put on their best phony smiles for me to please the boss.

"And, this is my office," Doug said as he showed me into the cluttered back room with a single desk, a filing cabinet and too much paper work. As I looked around, he closed the door behind me and locked it. He then took me by the shoulders and spun me to face him. I was more than strong enough to resist him but I didn't want too. I let him pin me to the wall. He placed his mouth on mine and kissed me with force. His tongue invaded my mouth immediately and I allowed it. I sucked greedily on it like I had before when we were younger. I really missed it. We kissed for a few minutes but it felt like hours. I didn't want it to end. I could feel his bulge in his pants pressing against mine. I had been hard since we touched hands. I reached down and grabbed his crotch. I wondered how many of his staff had been in the same position before. It only got me harder thinking of those hot babes on their knees, blowing him. Instinct came back to me and I soon found my way to my knees and unzipped Doug's designer pants.

I took his cock without hesitation into my mouth. It had been too long. I craved it. I desired it. I sucked with passion and licked his knob from tip to balls. I suckled gently on his testicles before returning to bathing his shaft with my mouth. He grabbed the back of my head and guided me. I opened up my throat and went deep. I took him to the root. My tongue licked his balls while his cock was embedded in my throat. I backed off and his cock glowed with the sheen of my saliva. He then began face fucking me. He pumped his prick into my mouth and down my throat. I barely gagged. All I wanted was for him to cum. I sucked him fast and viciously and he could not hold back. Within a few minutes after starting, Doug was unloading a pent up torrent of hot, sticky cum. I swallowed eagerly while maintaining eye contact. He kept his cock in my mouth until he was spent.