The Transition Team

My name is Teri. I'm a 26 year old lesbian. I'm what some people like to call a "lipstick lesbian". I live in a small town in the Midwest, so as you can imagine it wasn't easy coming out of the closet. I had my first lesbian experience in college when I was 19, and I came out of the closet a year later. When I told my male friends, almost all of them either offered to "change me back" or asked "Can I watch." All of them, except for Jason.

"Teri, I love you, and I want you to be happy. If this is what you want, then I am 100% behind you," he said. I'm pretty sure that I broke is heart that day, as I know that he had a bit of a crush on me. I've known him since we were in grade school. We have always been friends, but we became really close after I came out. He's sweet, supportive, and always there for me. He has bailed me out of more than one scrape, and I can talk to him about anything.

For years, we would cook for each other, watch movies together, and he turned me on to hockey. When we were both single, we'd hang out over at his house on Friday nights, get drunk and talk about "girl trouble."

He didn't date much. He was always shy, and I told him that all he needed some confidence. He would always say "yeah, yeah, yeah," and open another beer. He had been on a two year drought when he started to date Jane. They had met on one of his many attempts in on line dating.

At first, I was thrilled that he was dating. My excitement ended when I met her. She treated him like shit. She would put him down and crack the whip. I chose not to say anything to him at first, because he seemed happy.

After hanging out with the two of them for two months, I had had it with Jane. We had dinner at his place, and he made his specialty, chicken with a white wine sauce over penne noodles. It takes all day to make, as the meat needs to marinate in wine all day, and the red peppers are slow roasted. She turned her nose up at it, and bitched about how it was "too sweet" and how he needs to go to a cooking school, and the next time, she would cook. He tried to hide it, but I know that her reaction crushed him.

The next day, I went to his house. I felt that I had to free him from this bitch. She wasn't all that hot, and she was too self centered—there was no way that she was that good in bed.

"Hey," he said as he hugged me. "What are you doing here?"

"I have something I really need to talk to you about."

"Sure," he said as he led me into his place.

I was really nervous. Not a lot of people like to hear that you don't like his/her lover. People get defensive. Especially people who are as fiercely loyal as J. I really didn't how he was going to react.

"What's up?"

"I really need to talk to you about Jane."

"Yeah, I need to apologize for her last night. She's been under a lot of stress last night, and I know that she came off a little—" He searched for the next word.

"Bitchy."

"Yeah. I guess that's the word."

"J, it's not just last night. I haven't seen her act as a loving person since I met her."

His face tightened, getting defensive. "You just don't know her."

"No, I do know her. I just don't like her."

"Well, I'm sorry that you feel that way, because I do."

"I'm not that sure that you do." I waited for a second, waiting for him to retort. He just sat on his couch and sighed. "Am I right?"

He tightened his jaw. He took a deep breath and just shook his head. "I guess you know me well enough to know that I don't."

"Then why the hell do you put up with her?"

"I don't know."

"Yes you do."

"I don't want to say."

"Why?"

"Because you'll think less of me."

"Oh come on," I said. "Why would you think that?"

"Because it's a shallow reason."

"What is?"

He looked up at me. A tear was starting its way down his left cheek. "The only reason I'm with her is that she'll fuck me and no one else will."

I blinked. I didn't believe that believed that. "What?"

"Come on, Teri. It's not like I was getting anywhere with any of the other girls. She's the only one that would let me sleep with her."

"That can't be true."

"Well, it is. It's pathetic, I know. But that's who I am."

"So the only reason you're with her is because she's fucking you."

"Yeah, it is."

My mind was starting to turn. "So if you can find another girl to have sex with, Jane is a distant memory."

"Pretty much."

I thought about all the times that he was there for me. How much he gave for me. I couldn't believe that I was considering what I was thinking. "All right, I'll do it."

He looked at me, unsure of what I meant. "You'll do what?"

"I'll fuck you."

He studied me for a second, cracked a smile and started to laugh. "Good one, Teri. You almost had me for a second."

"I'm serious," I said. To prove my point, I took off my shirt and my bra. "See," I said. His mouth opened slightly. He just stared at my tits.

"Wait," he said. "You can't do this. You're a lesbian."

"I'm your best friend first. Lesbian second. I'll do anything to make you happy, and getting you away from that troll will make you happy. If this will do it, I will fuck you." I walked past him on the way to his bedroom. "Are you coming, or what?" He rushed after me.

I sat on his bed, and started to take my shoes off. He was standing by the door way, watching me. "Before we do this, we need to set some ground rules."

"OK."

"Rule number one, you have to dump Jane. Today."

"Done."

"Number two. I'm not your girlfriend, I'm your transition team. You still have to go out with other girls and find a suitable girl. One I approve of."

"OK."

I unbuttoned my jeans and pushed them down. "Three—you can't tell anyone about this. If word gets out, then the next girl you date will find out, and then there's that whole jealousy thing. So no public displays of affection, no kissing in front of anyone."

"Agreed."

"Four—I don't do anal."

"Fine."

"Five. I'm not going to bring any of my girlfriends over, so don't ask."

"I wouldn't think of it."

"Six—You have to wear a condom. I'm not on the pill."

"All right. And seven?"

I laid back on the bed and snapped my panties against my hips. "You have to take these off." He grinned. "You know, it's going to be hard to do this while you're dressed." Jason quickly took his clothes off and climbed into bed with me.

It was strange kissing him, but I needed to get myself ready. Judging by his six inch hard on, he was ready to party. His hands roamed all over my body, starting with my tits, and then he quickly moved his hands past the elastic band of my panties. I grabbed his wrist and pulled his hand out. He looked at me, shocked.

"Easy there, love. I'm not going anywhere. Take your time."

"OK," he said. We laid on our sides while we kissed and caressed each other for a while. After gathering up some courage, I moved my hand down and grabbed his dick. I felt him jump, and then he moved back a little, allowing me to slowly jack him off. He then moved his hand under my panties again, this time grabbing my ass. Nobody had ever grabbed it so firmly, massaging my left cheek. I gasped. It felt so good, and it made me feel so wanted.

"Oh, God." I whispered in his ear. I kissed my way down his stomach. I hadn't planned to give him a blow job, but I felt moved to do so. "Keep in mind, I haven't done this in a long time."

"No worries." I slowly started to lick the head, taking my time.

"Try not to cum in my mouth."

"OK." I took the whole it all in my mouth. J let out a long moan. His hand moved to my head. He ran his fingers through his hair. It felt so good. So loving. Nothing like what the guys I slept with in college did. Hell, it was more intimate than some of the girls I dated.

After a while, he pulled me up to him. He gave me a long kiss. "It's time to return the favor," he said. He kissed his way down my body. He bypassed my soaked panties and kissed my legs, slowly moving his tongue where my legs and crotch meet. He pushed the side of my panties over with his tongue. He slowly licked his way over to my pussy lips. I couldn't believe how good it felt.

"These need to go." He tugged on my panties as I raised my hips. He pulled them off with ease. There I was, naked in front of my best friend as he resumed eating me out. He found my clit almost immediately, and he lightly brushed his tongue across. He increased his speed, and then buried his face into my lightly trimmed bush. He relentlessly stayed, licking as if his life depended on it. He was much better than I anticipated. He was better than some of the girls that I dated. He stuck two fingers in my dripping cunt, and I came immediately. I couldn't take anymore. I closed my legs and moved away from him while I shuttered.

"Damn J. I'm going to have to make you an honorary lesbian."

"You liked that?"

"Yeah." I gasped. I sat up, and he did same. "Where are the condoms?"

"Top drawer". I reached over to his night stand and open the drawer. I grabbed a love glove and opened it.

"Allow me," I said as I rolled the condom over his throbbing dick. "So, do you love me?"

"Of course I do."

"Good," I said as I climbed on top of him. "Then fuck me." I grabbed his dick and led it into my hot slit. "GOD!" I cried out as I hit bottom. It had been eight years since I had a dick in me, and it felt so strange. I kissed him deeply as I moved my hips back and forth. He grabbed my ass again, working his fingers in between the crack. I almost stopped him, as I don't like my asshole touched, but he just brushed his finger across the opening, almost teasing me. I picked up the pace. It was the most incredible feeling, having someone I care about making me feel like a goddess. He then took his middle finger and started to push it up my ass.

"AHHHHHHHHH," I cried out. My legs started to shake, and I came, the first time I had ever done it while fucking a guy.

"I'm going to cum," he said.

"Do it. Do it now."

I could feel him stiffen and then he let out a cry. He held me close to him as we gently kiss. I could feel his cock getting softer. I reached down and grabbed the base of his dick and I got off. "You just fucked a dyke, and made her cum twice," I said. "How's that for confidence?"

He smiled and I suggested that we take a shower together. We got cleaned up, and he headed out to talk with Jane. I stayed behind and stayed naked. He came back and told me that he dumped her, and she didn't take it well. We celebrated by fucking all night long.

After that night, we spent the night together three nights out of the week. I had at least one orgasm every time we had sex. I really enjoyed the time that we had together, and I tinkered with the idea of talking him into making this a more permanent setting, but I realized that it wouldn't be fair to Jason. After about three months, he told me that he had met someone he really liked, and he thought that they had a chance. Even though it broke my heart a little, I told him that I loved him, and if that was what he wanted, I'd back him 100%. We spent one last night together, and I let him fuck me in the ass.

I met the girl a week later, and I can say that she is a sweet girl, and I love her for taking good care of my Jason. But there is a small part of me that wants her to screw it up. I'll be waiting.