"I just don't' know what to do anymore. She doesn't return any of my calls," my girlfriend Karen lamented as we talked on the phone. "We used to call each other every five minutes. Now all she wants to do is sleep."
"Give her time," I responded, in my usual comforting, but unhelpful way.
Karen was complaining about her best friend Annie, who'd been depressed ever since her boyfriend Rick broke up with her three weeks ago. Apparently Karen missed the good old days when they wasted every moment of their spare time giggling on the phone together.
"I'm gonna get going honey. I love you," I said.
"Awww. I love you too. Goodnight."
Karen was probably the best girlfriend a guy could hope for. She had a gorgeous face and beautiful blonde hair that hung down past her shoulders. She was barely five feet tall and she allowed me to smack her on the ass whenever I felt like it. She liked the feeling of my hand on her behind as much as I did. I could guarantee getting plenty of action by just slapping and groping her ass a little bit, even when she wasn't in the mood. Sooner or later she would rip my pants off and go down on me.
I'd been with seven girls before Karen, but she gave the first good blowjob that I ever had. She was a natural cocksucker. To top it all off, Karen was a very supportive, nice person who was wild for me.
But as much as I loved Karen, I could barely control my lust for other women. I am 24, the tail end of the age where a man feels he should be ejaculating 12 times a day, but at the beginning of the age where he's in control enough to get a lot of women to sleep with him. Lately I've been staring at every pair of tits and every short skirt that walks by. Some of the women are offended when they see me staring, but many of them take it as a compliment. I've been offered a few phone numbers, but I never accepted because I don't want to cheat on Karen. I never cheated on anyone and I always told myself I never would.
I hung up the phone and laid back on my bed, letting the conversation seep into my brain. Poor Annie was too depressed to get out of bed anymore. Annie was dating my best friend Rick, who dumped her for some big-titted secretary at his office, who is actually 10 years older than him. Annie didn't know about the secretary. She thought Rick just wanted some space.
I have fantasized about Annie for a long time. She is a daddy's-girl who dresses conservatively from the waist up, but routinely wears bottoms that accentuate her eye-popping ass. It's the kind of ass that causes involuntary erections. Every time she, Rick, Karen and I would walk through the mall together the men who were coming toward us just saw a normal 20-year-old girl on a shopping trip, which is what Annie looked like from the front. The guys who followed behind us invariably had their eyes glued on Annie's swaying buns and they were all trying to conceal their boners. There always seemed to be a lot more guys walking behind us than there were in front of us.
Rick never seemed to think much of Annie's butt, except for that she had a "nice ass." That's the understatement of the century. The only reason her ass was attainable for him was because she was only an above average looking girl from the front and she spent her whole life in an all-girls boarding school, so she didn't know that with an ass like hers, she could probably hold out for a rich oil billionaire.
As I laid on my bed I thought about what a shame it would be when Annie gets over Rick and tests the dating market. She'll never be available again. I don't know if I could ever cum hard again without having the sight of Annie's round butt swaying seductively back and forth to work me up. There were times I would think of Annie while Karen was sucking me off, especially if Annie was walking in front of me earlier. It was quite a show.
Last summer, Annie got drunk at a party and Rick put her to bed in a room upstairs. Rick came back down to party and Karen and I slipped upstairs to fool around. Annie was lying on the bed on her side, with her ass facing the door. She had only a purple thong and bra on. Rick must've undressed her and put her under the covers. The covers had apparently come off when she rolled onto her side. Karen was horny and didn't care that her passed-out friend was in the room. We fooled around for 20 minutes and soon she was sucking my dick. I stared at Annie's beautiful butt crack while Karen pumped her lips on my shaft. I wanted to reach out and slap that thong-clad ass while Karen worked my balls, but I knew Karen would get upset. Instead I leaned forward, as if I wanted Karen to approach things from a different angle, and put my face less than a foot away from Annie's ass. I almost lost control and started rubbing my face on it, but instead I casually rested my palm on her cheeks. I was cumming in seconds. I was so excited I forgot to tell Karen I was cumming, and I shot loads of jizz all over her face. It was the hardest I'd ever cummed in my life.
A really immoral thought came to my mind. I picked up the phone and dialed Annie's number. Maybe I could find a way to satisfy my craving for Annie's ass without Karen knowing about it. Annie wasn't stupid, but she could easily be talked into something. Annie answered the phone.
"Hello."
"Uh Annie, it's Tim."
"Oh. Hi," she said monotonously. I think she wanted to stay as far as possible from me, Karen or anyone else that reminded her of Rick. That was probably why she wasn't talking to Karen much.
"How are you feeling?"
"Fine," she said. An obvious lie.
"I know you're not feeling fine, Annie. I know what it's like to go through a bad breakup. I've been through six of them."
Annie remained silent on the other end of the phone. It wasn't an angry silence. It was a "I don't know what to say or what to do with myself" silence.
"Is there anything I can do for you?" I asked her.
"No. No thank you."
"Do you want some company. It's not healthy for you to just lay around by yourself in that empty house all day. Do you want me to have Karen come over?"
"I think I'd just rather be by myself."
"Why don't you talk to Karen anymore?"
"I just talked to her Tuesday."
"That was three days ago. You guys used to talk all the time." I paused. "Look, I'm gonna come over there and check up on you. I think I know something that can make you feel a little better."
"No don't. I'm in my pajamas already."
"That's okay. I'll be over in 20 minutes."
I hung up the phone. Annie was renting a room from a family for the summer and they were away on a month-long vacation. She was working two days a week and the rest of the time she sulked.
I hopped in the car and made the 15-mile drive to Annie's house. The porch lights were on when I got there.
I knocked on the door and Annie opened it in her pink pajamas. She opened the door and gave me a fake smile as she whisked me in. I asked her how she was doing and she said "good" without pondering the question. Her ass grazed my leg as she turned around and locked the door. I watched her and then followed her into the living room.
I almost developed an erection instantly, but I tried to calm down as I walked behind her. That was almost impossible because she was wearing the tightest pair of pajama bottoms I'd ever seen. They were see-through if you looked hard enough. I could see her panty line. It formed a frame around her wiggling ass as she strutted in front of me. Her top wasn't revealing, but her B-cup breasts stretched the fabric slightly. Her tits bounced slightly as she walked, which they didn't usually do, so I guessed she didn't have a bra on.
My eyes were fixated on her butt. I watched the panty line bend, straighten and then bend again repeatedly. She turned her head when she reached the living room and caught me staring at her ass. I casually looked up and slipped my hands into my pockets in a desperate attempt to hide my boner. She'd caught me looking at her ass before and she never made a big deal about it. We'd make awkward eye contact and then let it go. I didn't want her to catch me with an erection though. She might freak out, and that would ruin my plan.
"Um. Nice pajamas," I stammered.
"Thanks."
"So you're really doing okay?"
"Yeah," she said with a half-frown.
"Doesn't look like you are."
"I don't know"
"This is your first break up isn't it."
"It is," she said. She let out a laugh and a tear at the same time. "I didn't think it would be this hard."
She started crying quietly. I tried to comfort her with some cliches about dating, but I got no response. Rick was her first boyfriend and the first guy she'd done anything more than kissing with. She was still a virgin, although she'd done everything short of having sex with Rick.
Even though she was sexually naïve, Annie was used to attention. She was her father's little angel back at home. When she got to college, a few guys paid attention to her and Rick was very attentive to her needs. My guess was her current pissy mood was due more to lack of attention than genuine heartache. If someone out of the ordinary showed her some attention, I thought she'd snap out of her depression. I was out of the ordinary, but someone she was comfortable with. I had an idea that would make her feel better and make me feel like I was in heaven, but I had to be assertive.
I wrapped my arms around her and gave her a hug. She continued crying, but I could tell she welcomed the contact. She eventually stopped sobbing and tried to dry her tears while I hugged her. I snuck a peek at her voluptuous ass when I looked over her shoulder. It looked like she had a little "fuck me" sign planted in the middle.
"You're depressed. Nothing seems happy or interesting when you're depressed, but I know a way for you to get over it," I said.
"What?" she asked, still in my arms, but not hugging back.
