Oh Brother!

"You always did that better than any woman could," he complimented me as he wiped his cock off on my lip. When I rose up, he embraced me again and shared a sweet but salty kiss.

"Have you ever tried another guy?" I asked.

"Not really. There was a transvestite I fucked for a while a few years back who was pretty good. That was a bit of a messed up relationship though. He, I mean she was pretty talented too though.. With these girls, I usually just fuck them. Mind you, that's what gets me in trouble too," Doug said as he laughed. Doug had unzipped me and had my cock in his hand. I was still stiff as iron. He sat down in his chair and grabbed me by the ass. He pulled my crotch to his face and began sucking me off. I was a little shocked but pleased. His mouth felt so good. It had been so long since we were intimate or since I had been laid so it took hardly any time for me to cum. I squirted my load deep into Doug's mouth.

We were definitely on the mend again.

Over the course of the nest couple of years, Doug and I got together every now and then away from the rest of the family. We didn't always end up getting intimate but more often than not we did. Sometimes, Doug just needed help at the bar. I had bartending experience from the Air Force when I tended bar in the Officer's club two nights a week. At Doug's restaurant, staff rolled over so often and bartenders quit on him without notice so I would always come whenever he asked. Other times it was just big nights, like New Years eve, Saint Patrick's or football playoffs.

I started to develop a liking for football. It was partly about the athletic guys in the tight pants and the cheerleaders in their scantily clad outfits but it was a lot about the gambling. I got very good at picking teams, and beating the odds makers. I made a few bucks but Doug always took my advice and when he bet, he bet big. His wagers were beyond what I felt comfortable with. He made a small fortune on those bets. After one season of my help, he had enough to split ties with his company and buy his own place.

Doug's new place was the hit of the town. Everybody who was anybody came to the place. Before long, he was rolling in the money. Two ex wives and child support for three kids took care of a lot of that money but he was still better off than me or my other siblings.

For my birthday that year, Doug bought us tickets in VIP seats for a football game. It included a full service limo ride to and from the game. We drank scotch and I made sure to thank Doug by giving him a rim job all the way to the game. I had my tongue up his asshole, teasing him for half an hour in the back of the limo. It drove him crazy. He was hard the entire game. On the way back I sucked his cock so well he came in my mouth three times before we got home. Other times he came to me when he was having trouble with whatever girl he was seeing. I would be there to comfort him.

There was a girl he hired at his restaurant as a hostess named Jill. Jill was blonde, buxom and beautiful and a ten of course since Doug hired her. She was different then the others though. She wasn't a bimbo and she didn't fawn over Doug like the rest. She gave back as good as she got. She had a strong personality. She still slept with him but it was on her terms. He fell madly in love with her and after six months, he proposed to her. Six months later, they got married. She was not naïve. She knew his history. It didn't phase her though.

Other than on his wedding day when I sucked him off an hour before the wedding, Doug spent more time with his new wife and less with me. I was okay with that. Jill liked me and often had me over for dinner with them. She even liked playing with my hair. It was longer than hers at that point. She would mess with it and tell me how pretty my hair looked. Some times she even brushed it for me.

I did have a lot more time to myself and went back to my habits of watching porn, playing with dildos and butt plugs, and wearing lingerie around my apartment. I tried the gay bar again and after a few visits, met up with a pretty transvestite named Jane. We did hook up but we spent most of the night kissing. She was a bottom and told me that I was too. She usually went for more muscular, masculine guys but thought I was pretty enough to hang out with. She asked me if I ever cross dressed. I told her that I didn't since I considered wearing lingerie at home far from going all the way. She told me that it was a shame, that I could be a good looking transvestite. We finished our night with a mutual sixty-nine.

Jane and I remained friends but didn't have sex again after that night. She preferred the hard men for lovers. What she said had made me think though. I wanted to try it myself.

I had been thinking about Jane, the transvestite for a week. On the weekend, I went shopping at the mall. My purchases included hair extensions in my colour, makeup, false eye lashes, nail polish, a pair of black suede ankle booties, some pantyhose, a denim mini skirt, a white camisole and a girl's pink hoodie. It took me another week to work up the courage to try it all on.

I started the night early with a long hot bubble bath. I shaved my entire body below my eyebrows. I didn't have much hair and it was light blonde at that but it all went. After I oiled up my legs and threw on a robe. I did my makeup which took over two hours. When I added the hair extensions it was amazing how much I looked like a girl. I put on some white lace panties and a white bra. I had bought a pair of silicon rubber breast forms from the adult store. I slipped them into the bra and slid on some pantyhose. When I put the camisole, skirt and pink hoodie on, I looked amazing. I wanted to fuck myself. I put on the shoes which had a three inch heel. I tried walking around the apartment to see if could manage the girl walk. I had practiced for a few hours each night in the heels since I bought them.

Confident that I looked good, I left my apartment and walked the four blocks down town to the gay night club. I wasn't even at the club before a guy tried to pick me up. I don't think he knew that I wasn't a real girl. A car drove by and the guys all whistled at me. By the time I got to the club, my confidence was way up. Right away some guy handed me a drink. I didn't buy one for myself all night. Guys lined up to ask me to dance too. I went home with a polite, good looking guy that night who made me feel good, pretty and wanted. I eagerly sucked him and when he told me that he wanted to fuck me, I was nervous but I let him. I still had some fear from when Doug raped me but the guy was gentle and easy on me. I actually really enjoyed it. I even came myself while getting ploughed.

For a few more weeks I went there on the weekends, always met a man and took him home. I felt really great and went on to expand my wardrobe of female attire. I bought dresses, skirts, blouses, hosiery and high heel shoes.

The doctor interrupted me, "Sorry, we're out of time for this week. We'll pick it up right there on your next visit Molly." I didn't want to break it there as I was really on a roll with the confessions. Sadly, I left the office and waited impatiently for the next visit.

The following week, I was early to see my therapist, Doctor Carter and pick up where we left off. When I finally got in the chair she asked me, "You finally got back with your brother Doug and then he went and got married. You seem to have moved away from him again. How did that make you feel?"

"At first, I was a bit disappointed but like I said, I got along great with his wife Jill an we remained friendly," I answered. I was doing my own thing for a while. I went out dressed like that more often but I never told Doug about it. About a year past. Jill had a baby girl. I still was in their lives. I still tended bar once in a while. Jill was good for him. She was strong in many ways. He loved her very much too, much more than his previous wives who had trapped him into their relationships. With Jill, he chose it.

One day Jill called me up and asked me to come over. I went as I expected to see both her and my brother. Jill was alone however and sat me down to have a personal chat. She asked me if anything was wrong between Doug and I. I told her that we were fine and was curious why she would ask.

Jill held my hand and told me Doug was worried that I was not happy with him again. "No, that's silly. Why would he think that?" I asked.

Jill took a deep breath and exhaled, "He's worried because you haven't had sex with him in over a year and he is too afraid to ask you for it, given the past."

I was shocked to hear her tell me that. She knew. I had no idea that Doug would have confessed to her about his relations with me. "I'm sorry Jill. I'm not sure I follow. What do you mean?"

"Marty, I've known about you two all along. It's not a secret between Doug and I. I asked him about it right after I met you for the first time and he told me everything. He told me about teaching you when you two were younger and how he forced himself on you. That drove you away for a long time but you came back. He was so happy that you did. He really loves you. You have no idea how much. I'm okay with that too. The bond you two share is beautiful. I can't blame him either. You're gorgeous and Doug tells me that you are a better cock sucker than any girl he's ever known, including me," Jill said.

I wasn't sure how to reply to that but since the cat was out of the bag, I confessed it all. "Jill, I stopped out of respect for you and your marriage. Doug had a cheating history and I didn't want to be the one to come between you two. I love you both," I said.

"Yes, I know all about Doug's affairs. He was always a Casanova. That's one of the things I love about him. I know that he still fucks some of his waitresses now and then, but he always tells me. You can't change him completely but I have him being more responsible and accountable. He probably wouldn't do any of them any more if you were his only side action. You are by far his favourite. I would feel better if you were still having sex with him. So I'm asking this as a favour to me Marty. Please," Jill pleaded.

I hugged her close and she squeezed me tight. Her big breasts squished against my chest. She kissed my cheek. "I will Jill. Thank you," I promised her. She gave me a big kiss on the mouth. It was closed mouth but sweet and long. I wondered if we were going to go farther but she broke our embrace and stood up. She was teary eyed and blushing. We finished our tea as we talked about clothes and hair and other girly stuff. I was glad for our talk. It made feel more powerful than I had ever felt in my relationship with Doug.

That brings us to the night of the championship party. Our football team won the cup as you may have heard. I told Doug to give three more points over the five point spread. He did and it brought in a ton of action. Our boys won by ten in the final and Doug cleaned up. I made a few hundred myself. Doug was already tight with a bunch of players on the team. They often came to his restaurant and hung out at the bar. I had seen a few of them around myself. It wasn't a big surprise when Doug told me that he made arrangements with the team owner and would be hosting the victory party. He asked me to come in and work the bar as it would be a private function, closed off to the public. I agreed of course. A closed function meant bending some of the rules. He brought in strippers and some call girls paid Doug off to allow them into the function. Football players are big spenders. I would get a hundred bucks from Doug but that was nothing compared to the tips I was likely to make.

I wore my usual black dress pants, a white shirt and a red vest. I was showered and clean shaved. I had my long hair in a ponytail mostly for functionality. It also made me look less girly. Sure enough the party was a big money maker for me. The football players drank a lot and tipped well. I was over four hundred in two hours. Most of the players just threw the money my way without taking much notice of me. There were some speeches, toasts and general revelry. After a while the crowd began to thin out. The abstainers, family men and old were the first to leave. The strippers and call girls all ended up leaving with someone. After that it was just the hardcore drinkers and partiers left which was just a few guys.

Reggie, the all star defensive end and defensive MVP of the game was one of them. He spent most of his night hanging out with Doug. They seemed pretty tight. I had watched him tipping the strippers and enjoying his scotch. He was very friendly and amiable, a complete contradiction to the beast he was on the grid iron. Reggie had come to the bar several times for drinks, often buying rounds for his buddies. He was a big man at six foot seven and two hundred and fifty-five pounds. He had been in the league for ten years and was a team captain but it was his first cup. He was the happiest man in the room.

Whenever Reggie came to the bar, he made conversation with me. He had intense brown eyes, predominant cheek bones and a big white grin which contrasted his very dark, black skin. He seemed to stare inside me when he talked. The first time he came to the bar, he asked my name. He was courteous and polite.

Of course there was the conversation that I heard so many times. "I can't believe you and Doug are brothers. You two look so much different."

"Ya, we get that a lot. Let's just say that our Mom got around," I answered, Reggie laughed hysterically. I had to laugh along with him.

The next time he came to the bar he asked, "Hey Marty, did you watch the game?" as though he didn't expect me to have. Maybe it was my effeminate look.

"Sure I did Reggie. It was a great game. Your sack in the fourth quarter saved the game. It also made me three hundred bucks, so thanks," I answered with a smile.

"Well then, I guess you owe me one Marty," he teased as he laughed. I laughed along with him and freshened his drink. After that he seemed to find excuses to come to the bar, volunteering to buy rounds and such. Each time, he made time to chat with me. He always had that smile and those intense eyes. I felt disarmed.

In the late hours, two of the last three players stumbled out the door to their awaiting ride. That left just Reggie who was still talking with Doug. Doug had the remote control for the big screen. It had been showing football highlights all night. He clicked it onto something else. A few minutes later, Doug and Reggie were laughing and smirking. I noticed them both looking over at me and staring which was making me feel uncomfortable. I had just finished cleaning up and taking out the garbage, preparing to close. Doug came over and told me that he and Reggie had been working on a business deal. He said that he was close to making a deal. Then he said to grab three glasses, the bottle of Oban and bring it over to the table. He was inviting me to join the two of them. I figured that I deserved a night cap for all my hard work and Reggie was good company so I gladly grabbed three chilled glasses and the new bottle of scotch and brought them over to the booth.

The booth was a comfortable couch for VIP guests, curved in shape and padded with plush purple cushions. I set the glasses out and poured three stiff ones for us. I took the elastic out of my hair and let my blonde mane flow. We had an obligatory toast to the victory and I sat down. Reggie was grinning at me as he talked to my brother, "He sure is a pretty one Doug. Ought to be in a dress this one, if you ask me." I swore I saw him lick his lips.

Slightly embarrassed, I turned to look at the screen. That's when I noticed that football had been replaced by porn. It wasn't just regular porn either. The film was of a transsexual actress getting gang banged by four men. The actress was blonde with big fake boobs and was sporting a huge hard on as she got fucked. My jaw dropped as I stared at the screen. My eyes were glued to the action on the screen. I downed my scotch and poured myself another big glass. The men were taking turns in her mouth and her butt. The whole time she kept a stiff erection. There was no sound for the movie as the music was still playing over the house system. As I watched though, I could hear the sounds of sex. I shook my head and turned to acquire the sound of the source.

I had been watching the screen so intensely that I had missed out on what was happing in the real world. Reggie was leaning back, sprawled out comfortably watching the screen too. His pants were undone and his cock was out. Doug had his face in his lap and was licking Reggie's ten inch long, black meat pole. I had never seen a cock so big in my life. My eyes bugged out. Doug had his own pants open and was stroking his own cock with his hand. Reggie caught me staring and smiled a big grin at me. Then he winked at me.

I could tell it was an invitation. He and Doug had to have been closer than I knew. It looked more than spontaneous. Still, I could not resist the temptation. I was also feeling guilt free after getting Jill's blessing. I moved closer to them and removed Doug's hand from his cock and replaced it with my mouth. I engulfed his familiar prick between my sweet lips and sucked him. It had been a long time since I had his cock in my mouth and I savored it, enjoying the taste, feel, smell and heat that I remembered so well. I was so horny at the scene that my own cock was hard as iron and straining my pants. I arched my back to avoid it rubbing on the cushion. That made my ass stick up in the air. I didn't want to come too soon but wanted to enjoy the moment so I avoided touching myself and concentrated on sucking off my brother while he worked on the big dick of his guest.

Reggie moaned, "Mmm, look at that sweet ass. Ya, that bitch should be in a dress." Doug took his face away from Reggie's cock and looked back at me. We made eye contact. I had his entire hard on deep in my throat. Doug smiled and licked his lips. His brown eyes were full of passion. He winked at me then turned his eyes to Reggie's huge erection which was slick with saliva. Then he looked back at me and I understood his unspoken language.

I released Doug's cock from my mouth leaving a long wet trail of saliva. I greedily licked it all up and ate it as I stared at my new objective. Like a cat, I crawled up on all fours to where Doug had his face in Reggie's crotch. I breathed in the deep smell of cock and smiled. Then I kissed my brother on the mouth, hard and fierce. We exchanged a loving embrace before I turned my head to the giant black monolith in front of me. I turned my head and kissed it with respect. Reggie quickly pulled his pants all the way off then repositioned himself back in the same place.

Doug sat up to watch me work. He giggled and pronounced, "Look out Reggie. You're in for it now. Here comes Marty, the best cock sucker this side of Montreal." As he hyped me, I teased Reggie's meat with my tongue, taking long slow licks up and down the shaft. Reggie moaned and began running his fingers through my long hair.

Doug maneuvered down a bit and began loosening my pants. I didn't fight him as he slid my trousers right off. I kicked my own shoes and socks off to help. After my pants hit the floor, Doug went behind me and started licking my swollen balls. That got me hotter and I started to really work Reggie's huge cock as I tried to live up to my hype. I sucked hard on the meaty head as I swilled my tongue around the cap. As I did that, I started pumping the enormous shaft with my left hand as I fondled his balls with the other. Reggie seemed to really be enjoying it. He kept encouraging me, telling me what a great cock sucker I was.