Loading...“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.
“Well, it’s going to sound strange, but I know it works. Just do what I tell you.”
“Um… okay.”
“You’ll just have to trust me on this one. Now relax. You’re tense. Relax your muscles and pretend you don’t have a care in the world.”
I massaged Annie’s shoulders. She closed her eyes and let loose. I started kissing her cheek and she put her hand up and stopped me.
“This isn’t right. Did you forget about Karen, the girl you’re probably going to marry someday. Don’t you think I’d tell her if we did anything together,” Annie said.
“I’m not hitting on you. It’s all part of the massage,” I said. “I’m trying to make you feel better. Now no more questions.”
Annie didn’t know whether to stop and walk out disgusted or to listen and let me continue. She opted to let me continue.
I kept rubbing her shoulders and slowly worked my way down to her middle back. I lightly kissed her cheek and her neck. Annie just stood there, unresponsive to the massage. I wasn’t discouraged though, because I was working up to something. In a couple minutes my hands would be all over her curvaceous ass.
I kept kissing her neck and dropped my hands down to her lower back, near the line of her pajama bottoms. I worked my fingers over her skin, trying to time my move to her butt perfectly. By now Annie’s breathing was a little irregular.
I slid my hands down to the top of her ass and pushed it in with my fingers. I made little circles, which made the bottom of her ass jiggle, much to my delight. I continued kissing her cheeks, neck and forehead as I lowered my hands and groped her ass through her pajama bottoms. I had two tight orbs of flesh cupped in my hands and my dick became rock hard. It pressed up against her pussy and she tried to push away from me.
“Relax,” I ordered. “It’s okay. Don’t think, just relax.”
I stopped kissing Annie and started to fondle her ass more violently. I squeezed and let go and squeezed again, making it my mission to grope her harder than she’d ever been groped before. I alternated squeezing her bottom with rubbing it. I rubbed her ass quickly, like sandpaper on wood. She seemed a little uneasy that I was playing with her backside so much, but she didn’t say anything.
I kept rubbing her ass the same way, but now I ended every couple of strokes with a smack. I wanted to let her know who the boss of her ass was. After a few smacks I grabbed her by the arm and turned her around, so her back was facing me. I cupped her butt and started rubbing it again. My cock twitched with desire each time I ran my hands over her pajama-covered ass. Now when I spanked her I thrust my pelvis forward too. My dick pushed up against her bottom each time. Annie’s butt cheeks swallowed the tip of my dick briefly once. I thought I was going to cum in my pants.
While I fondled her, I whispered in her ear “I’m going to take your pants off.” I expected her to put up a fight, but she didn’t respond. I slid my thumbs into the waistband of her bottoms and yanked the tight pants off of her, along with her orange panties. I pulled the clothing all the way down over her feet and left the pajamas on the ground. I grabbed the panties and stuffed them into my pants pocket. Then I turned my attention to Annie’s naked ass.
I instinctively gave Annie a slap on the butt. Her buns jiggled like they were made of jello. I felt like getting down on my knees and kissing her butt cheeks while I fondled them, but I didn’t want her to forget I was in charge. Instead I sat down on the couch and pulled Annie over my knee. I felt wet heat touch against my bare knee. That surprised me because Annie didn’t seem that enthusiastic about what I was doing to her.
Once she was secure, I started lightly spanking her right ass cheek. Then I worked over the left one. The smacks didn’t seem to hurt her much.
The sight of her creamy white ass jiggling at my will got my dick rock hard. I alternated slapping her left and right ass cheeks, softly, but hard enough for her to feel it. My dick poked up between her bare legs. It was no good trying to conceal it anymore.
I squeezed Annie’s ass with both my hands and then pinched it. She flinched like she’d been stung by a bee. When she flinched she accidentally rubbed both her legs up and down the length of my penis, causing waves of pleasure to shoot through my body. At one point while I was greedily fingering her ass, I thought my fingertips were going to have an orgasm of their own. The sight of Annie’s buns, the feel of her skin and the smell of her moistening cunt was a sensory overload.
Now I felt like giving her a real spanking. I stopped slapping her ass and gave it a quick rub with both my hands. Then I pulled my right hand up and brought it down hard on her orgasmically beautiful butt cheeks.
SMACK!!!! Annie jerked up violently.
“Owww! What the fuck Tim!” I didn’t even acknowledge her.
SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!!
“Stop it!,” Annie said, trying to wiggle out of my grasp. I held her down with my left hand fairly easily.
“I’m teaching you a lesson. You’re not so high and mighty,” I told her as I continued to spank her. “You’re just a play toy. Don’t expect every guy to fall in love with you.”
Annie needed to learn this. I figured if I could make her a little less uptight and a lot more submissive I’d be doing her a favor. I knew she was submissive at heart and the reason she wasn’t finding the right kind of guys was she came off as a prude.
Annie started to concentrate on absorbing my hard spanks so much that she couldn’t respond coherently. I kept working on those reddening buns.
SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!!
Annie was now having a tough time handling the pain. She started thrashing her legs back and forth, rubbing my excited dick in the process. It felt like I was fucking her thighs. It was better than a hand job. Annie’s legs went back and forth, back and forth, back and forth. My right knee was wet with Annie’s love juices.
“Who owns your ass?” I asked Annie as she inadvertently masturbated me. She didn’t say any thing, so I decided to startle her. “WHO OWNS YOUR ASS, BITCH!” I shouted as I gave her the hardest slap of the night.
“Owww! You do! You do! You do!” Annie said quickly.
“Say it again!”
“You own my ass!”
“I can do whatever I want to your sexy little ass, can’t I? You teased me long enough with those tight shorts you wear and skimpy bathing suits. You’re lucky I’ve never spanked you before.”
SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!! SMACK!!!!
I stopped spanking Annie for a second and told her to get up. I was afraid I was going to cum in my pants with the way her thighs were jerking me off. She quickly popped up off my knee and started rubbing her ass. It was a hot sight. I even felt a little bit of pre-cum drip onto my boxer shorts while I watched her move her delicate hands over her luscious behind.
“Bend over.”
Annie rubbed her ass a little bit more and bent over. I had seen her bend over in tight jeans a million times and had a detailed mental picture of each one, but the sight of her bending over naked, with her pussy and asshole exposed was so stimulating I almost lost control of myself. I walked up behind Annie and smacked her right in the middle of her ass. I rubbed her round bottom a little bit and then slapped it again.
“Give me one good reason I shouldn’t stick my dick in your pussy,” I said.
“Because I’m a virgin,” Annie said.
“You’re lucky you are or I would be fucking the shit out of you right now.” I noticed Annie moved her head up a little to answer me, causing her ass to droop a little. “And keep your ass up!”
Annie arched her back even more. Her ass rose to the level of my dick.
“You’re lucky I have some morals or you wouldn’t be an ass virgin anymore.”
I gave Annie a few more smacks and then unbuckled my shorts. I had to pull the boxer shorts over my throbbing member. Annie heard me undo my shorts, but remained in the bent over position I assigned to her. I walked up to her and pressed my dick into her left ass cheek. She let out a gasp when she realized what was touching her, but didn’t say anything. I rubbed her right ass cheek feverishly as I pushed my meat against her flesh. I could barely take the stimulation anymore. I told Annie to get up and I grabbed her arm, dragging her to the middle of the room. I placed her near a full-length mirror, allowing me to face her, but still oggle her gorgeous butt. I pulled her shirt over her head and discovered that I was correct, she wasn’t wearing a bra.
“Suck my dick until I cum,” I commanded.
“I’m not good at it.”
“You will be, because I’m going to spank you more if you slow down.”
Annie gently clasped my penis in her right hand and stroked it. She bent her knees to bring her mouth to my cock.
“Keep your ass in the air,” I said as I reached down and spanked her. She brought her knees back up and bent her back instead. She put her mouth on my cock and bobbed up and down on it. I stared at the reflection of her naked butt. Her mouth was warm and I could feel the cum gathering in my balls. I was on the verge of an orgasm almost immediately, but her technique was such that every time I neared the point of no return, she slowed down. I stood there on the threshold of filling her 20-year-old throat with my semen for about 10 minutes. I bent forward slightly and started spanking her with my right hand and groping her tits with my left hand. She sped up as the frequency of my spanks increased. She started sucking with the confidence of a porn star and I was ready to blow my load. I had the urge to fuck something right before I came though. Her ass and pussy were out of question for now, so I put both of my hands on her head and steadied it. I then started pushing my dick in and out of her mouth, much harder than she could do it herself.
“I’m fucking your face, slut!” I said as I pumped my dick into her gorgeous mouth. I pushed hard enough to move her entire body, causing her tits and ass cheeks to wiggle. The sight of that did it for me. I felt the cum race from the base of my dick to the tip of my head and ejaculate into Annie’s warm mouth. I spanked her ass as I was cumming, which caused even the smallest drop of semen to come flying out. Annie pushed me away to try to get some air and the last bit of cum landed on her tits and face.
Annie fell to the ground and gasped for breath, swallowing my salty load in the process. She was stunned by how aggressive I was, but she didn’t seem scared. I walked over to the couch and laid down. Annie was still sitting up on the ground, with her arms clutched around her knees. My dick softened into a semi-erection. I was exhausted, but the sight of Annie naked still stimulated me enough to keep me from going limp. I laid on the couch for a couple of minutes without moving. I could see Annie’s pink pussy lips and one of her tender nipples. When Annie finally started to stir, I got up.
“Do you feel any better?” I asked her.
“I don’t know.”
“You will in a few hours.”
Annie got up and hopped into her pink pajama bottoms again. Her ass cheeks wiggled slightly when she pulled the tight fabric around her thighs. That gave me an erection again. Annie finished slipping her pants over her ass crack and looked down at my boner in disbelief, wondering if I would try to fuck her mouth again. I hovered over Annie and spoke.
“You’re not going to tell anyone about our little therapy session are you?” I asked as my naked dick pressed against the side of her hips.
“No.”
“Damn right you won’t.”
I gave her ass a hard swat with my right hand. My cock stood straight up.
“I ha… have to go to bed now. I have to be at work really early in the morning tomorrow,” Annie said, trembling slightly.
“I’ll bet you do,” I said as I rubbed her butt with both of my hands.
“I really do, so you’ll have to get going.”
I decided to let Annie go to bed. There was probably a better chance she wouldn’t tell Karen about our affair if I didn’t try to spank her and fuck her mouth a second time anyway. I carefully pulled my pants over my erect penis and zipped up. Annie pulled her shirt back on.
“Walk me out,” I commanded. Annie walked to the t.v. room doorway and waited for me to pass her. “Walk in front of me.” Annie stepped into the hallway and I lowered my eyes to her swaying hips and fuckable ass, like I did when I came in. Only this time I was less shy. I cupped both my hands on her jiggling buns, which caused her to walk quicker. I followed quickly behind her and spanked both of her butt cheeks a couple of times. We finally reached the door, just as I felt the desire to fuck her ass or pussy reach uncontrollable heights. I stood in the doorway and groped Annie’s ass violently in full view of any neighbors who might have stayed up late. I moved my left hand to her tits and rubbed my raging dick on her cotton-protected pussy.
Annie opened the storm door while I was busying myself.
“It’s time to go. Goodnight,” Annie said as she pushed me out the door. I felt like breaking back in and trying to fuck her, but even in my present state that was a little over the top, I thought. Instead I walked quickly to my car and got in. I zipped down my pants and pulled Annie’s pretty orange panties out of my pocket. I wrapped the silky fabric around my aroused dick and pumped up and down like a repressed teenager. I pictured Annie’s ass vibrating after each time I smacked it and fantasized about taking her virginity. The fabric of the panties felt good on my sensitive dick. After about 30 seconds I was shooting loads of cum onto my shirt. I wiped the cum up with Annie’s panties and drove home.
I woke up the next morning with a bad feeling. I checked my cell phone and sure enough I had two voicemails, two from Karen and one from Annie. I was sure I was busted.
I listened to the first one from Karen. All she said was “wake up sleepy head.” The second one was a bit more discouraging. “Hello jerk! Give me a call back to talk about Friday. I am soooo mad at you right now.” The third one was a surprise. It was Annie asking me to come over that night at 9 p.m. Were they going to confront me? It didn’t sound like it based on the tone of her voice, but it was certainly possible.
I called up Karen expecting the worst.
“Hey Karen, it’s Tim.”
“Hi honey. What’s up?”
“Nothing. You?”
“Nothing… Oh! Except you’re a big jerk!”
“A big jerk? Why?”
“Because you haven’t told me what you want to do Friday.”
“Friday?”
“For your birthday, silly.”
“Oh. My birthday.”
“Yeah. Of course you know I’ll let you do whatever you want to me.”
“Oooh. Sounds hot,” I said.
After work I checked my voicemail again and found Annie had called again. She was pleading with me to come over again. I smiled knowing that in four hours my hands would be all over the hottest ass I’d ever seen, while my cute girlfriend sat at home planning my birthday party. Maybe I’ll bring my condoms this time.