An Anna Afternoon

It was the summer after graduation. As with any college-bound kid, I was trying to fit as much as I could into those two months. The preparation for going off to school was daunting enough along with working full time at the job I'd had since I turned 16. I also had a serious relationship that was in its third year. My girlfriend, Amanda and I had a solid thing going and I was truly happy about it. We were going our separate ways to different colleges but would only be about 90 minutes from each other and already had a plan to visit once per week as well as seeing each other on the weekends when we would both return home to continue working. Amanda was gorgeous, with a bob of red hair just above her shoulders, beautiful, B-cup tits that defied gravity and hips that were absolutely perfect for grabbing and holding during sex. We had a great sexual relationship and I had absolutely no complaints.

The one complication was Anna.

Anna was our mutual best friend and we both loved her to pieces. We'd all been friends for years and she dated one of my best friends, Jeff. There had long been a flirtatious nature between Anna and I and we were completely open about it. There was never any jealousy, concern, or issue with our banter. As we were getting older, however, the sexual tension had become more than palpable.

Anna was the same height as Amanda, about 5'3", and very thin. She had small hips and a tight little ass with very small breasts. Her long, blonde, hair came to halfway down her back and was perfectly straight. She had a smirk and a sass that just made me want to...well, there's no other way to put it...own her in bed. Don't get me wrong. I knew it would be a challenge and I suspected a right fun one at that.

The temptation was even greater as we only lived four blocks from one another. She lived with her mom and they had a rather fraught relationship at times. She would occasionally call and say "I need to get out of the house." and we'd spend an afternoon or evening watching a movie and just hanging out. Sometimes, this happened with Amanda and sometimes not.

One afternoon in June, I got such a call and told her to come over and we would laugh and get her mind off of things. She arrived fifteen minutes later and followed me into the kitchen. Amanda was working that entire afternoon/evening and I wouldn't see her for the rest of the day. After getting each of us a drink, I excused myself to the powder room quickly and, when I emerged, Anna was no longer in the kitchen. In fact, she wasn't downstairs at all anymore. I called out "Where'd you go?" and she quickly responded with "I'm up here." I thought that, maybe, she ran upstairs to use the other bathroom. In any case, I walked upstairs. I was surprised to find her sitting on my bed.

I should take a moment to describe her outfit that day. She was wearing tight jeans as was normally the case with her. Her shirt was a denim button-down with Mickey Mouse on the front of it. The placement of Mickey's hands was odd on this particular shirt and one of them actually wasn't visible, looking as though it was inside of her shirt. It was a running joke whenever she'd wear it and someone would always ask where, exactly, Mickey's other hand was and what it was up to.

Seeing her sitting on my bed, I wasn't really sure what to say. I managed a "What's up?" and felt like an idiot. She stood up and closed the small gap between us. There might have been three inches between the tips of our noses. Anna quietly said "Tell me what you want right in this moment." Without hesitation, I replied "I really want to kiss you."

"Then, I think you should."

I leaned in and softly pressed my lips to hers. She tilted her head slightly and parted her lips as our tongues just touched. We retreated for an instant and then resumed with an even deeper, more passionate kiss. My arms were already around her and I slowly slid my hands down to her ass; firm and small enough to fit into my palms. She stepped back and sat back down on the edge of the bed, smirking. "I think you should find out where Mickey's other hand is." I wasted no time. Kneeling on the floor, between her legs, I began unbuttoning her denim shirt from the top down. Reaching the bottom button, I pulled the tails of her shirt from within her jeans and then reached up to slide it off of her shoulders. She reached back and pulled it from her arms, tossing it to the floor. Holding her sides, I slid my thumbs across her pale, perfect skin and then moved my hands around to her back...unclasping her bra. She had the most magnificent, martini glass tits that I've ever seen. I rubbed my thumb across one hardened nipple and leaned in to take the other between my lips. Swirling my tongue around it several times, I sucked gently and garnered a gasp and an "Mmmmm" from Anna.

She reached down and began to bunch my shirt up in her hands, pulling it upwards in an effort to remove it from me. I reached up and grabbed the collar, pulling it over my head and tossing it on the floor with hers.

At this point, I had to reach down and reposition myself within my jeans as I'd become fully erect. The movement wasn't lost on her and she whispered "Stand up." I did as I was told and heard her say "Oh, damn." I laughed and said "Don't flatter me. It's average." Anna ran her hands up my thighs and then one flattened palm up my crotch, against my straining cock. She made surprisingly quick work of my belt, button and zipper and slid my jeans down my legs. At the time, I wore briefs and they were small enough that the head of my cock was protruding above the elastic band...a large drop of precum sitting atop. She immediately hooked her fingers into the elastic and slid my briefs down to join my jeans. As she did so, she gasped "Fuck." I began to reply "It's only six..." and she cut me off with a curt "It's twice as thick as Jeff's."

"Oh." was all I could answer as I smiled inwardly.

She brushed a fingertip across the tip and touched it to her tongue...tasting my precum. "It's so sweet!" she smiled and leaned toward me, flicking her tongue against the head of my cock and capturing the remaining dollop of clear, viscous liquid. She then wrapped her hand around me. "My fingertips don't even touch. Wow." She squeezed lightly and then said "I think you should lay down." I stepped out of my clothes that were around my ankles and sat on the bed before laying flat on my back. Anna stood up, undid her jeans and slid them to the ground, stepping out of them and leaving on her pair of cute and unassuming panties.

She climbed onto the bed and crawled on her hands and knees over my body and up to kiss me. She laid her lithe body atop mine and began to kiss me deeply. I ran my hands up and down her back as we made out properly. Sliding them over her skin, inside of her panties and back up to her shoulders. I could feel the warmth of her sex through the cotton of her underwear and against my cock. I felt more precum oozing from my cock with a tickling sensation as she parted lips with me and began kissing down my neck...to my chest...to my stomach. She was propped up on her hands and knees again when she stopped just over my painfully-hard cock. She leaned in and slowly ran her flattened tongue from the base to the tip, eliciting a low moan from me. As she reached the head, she took one hand and gripped me, pulling the shaft outward and closing her mouth over my cock. She stopped abruptly and said "I can barely fit it in my mouth. Am I scraping you with my teeth?" I told her that I wasn't sure and asked if I could let her know in half an hour. She laughed loudly before taking me back into her mouth and swirling her tongue around the head of my cock. I gasped and moaned words of encouragement.

She began to descend deeper, taking more and more of me into her mouth and milking more precum from me every time she would ascend. "I love how much of this sweet stuff you keep giving me. If I hadn't seen it, I'd have sworn you were cumming slowly." I replied simply "When I cum, you won't have to wonder. You'll be absolutely sure."

She looked up at me and stopped long enough to ask "That much or that hard?"

I stared back in reply.

"Both?!" she said.

"You'll have to let me know." I smirked back at her.

She shrugged with a smile and said "We'll see." as she rolled to the side of one leg, laying on the bed and against me as she propped herself up on one elbow for support. She used her other hand to grip the base of my cock and hold me as she continued working it with her warm, incredible mouth. Amanda was perfectly proficient at giving a blowjob but Anna knew how to suck cock. There is a difference that I hadn't appreciated until I was in her mouth. She wasn't afraid to keep things wet. There was a thick coating of saliva covering my shaft and pooling at the base, even covering my balls. She wasn't shy about making any noise either. She sucked and slurped shamelessly and it just made the experience that much hotter for me.

Trying to be polite, I whispered "You're going to make me cum soon."

Suck. Slurp. "That's the idea." Right back into her mouth...brushing the back of her throat.

"Do you want me to let you know just before I do?"

She pulled her mouth off of me with a pop and began stroking my well-lubricated cock as she looked up and said "You just lay there and enjoy it and I'll see if I can swallow fast enough to keep up."

I smiled as she took me back into her mouth with a renewed vigor and enthusiasm.

That was it. I couldn't hold back any longer. My hips began to buck just a bit and the first stream of cum left the tip of my cock and hit the back of her throat. I wasn't exactly in any condition to count but I had to have let at least another half dozen volleys into her mouth. It was enough that I could hear her swallow hard at one point. As my orgasm subsided and I settled my weight back onto the bed, she looked up at me and smirked...a bit of cum rolling down from the corner of her mouth. She wiped it upwards with her finger and cleaned it off, saying "Ok. Yeah. That was a lot of fucking cum. I didn't really need to worry about swallowing fast enough. You shot most of it straight down my throat."

Did I mention how amazing it felt to fill her mouth? My. Fucking. Goodness. The girl had a gift. She clearly enjoyed sucking cock, or, at least, she clearly enjoyed sucking my cock on that particular day. I don't really care either way. I just know that I've never cum so fast from oral sex and that I also had to fight the urge to fuck her mouth as I began to do so.

"Your turn." I said with my own smirk.

Anna replied "Yeah, but you don't look like you're in any shape to get up yet, so..." She stood and swiftly removed her panties to reveal a beautiful, perfectly-shaven pussy. My mouth probably fell open a bit as she smiled at my reaction. She then began to climb back onto the bed and finished her sentence with "...let's do this." as she raised herself up and straddled my face.

"Oh, it would be my pleasure." was my answer.

"It had better be my pleasure." Anna retorted.

"It will be." I said as I wrapped my hands over the backs of her thighs and slowly parted her wet, smooth lips with my tongue.

"Oh, fuck!" she said as she leaned forward a bit and braced herself on her hands, placing them on the pillow over my head.

I wasn't shy in my approach as she seemed more than ready to be pleasured. I trailed my tongue up to her clit and flicked it across the sensitive nub. She moaned in response and only got louder when I took her between my lips. I swirled my tongue. I ran it against her. I rubbed and sucked her with my lips. All the while, I gripped her hips and held her tightly to my mouth as my oral assault became more and more vigorous. I began to flutter my tongue against her clit and I thought she was going to scream. Her breathing became faster and ragged. I continued what I was doing...wanting to feel her cum against my tongue. The combination of my lips and tongue finally pushed her over the edge as she began to shake over me. I could feel her ball her fists into the pillow as she moaned and cried out in pleasure. I never once slowed my ministrations and had hoped to push her through the first orgasm and into a second. She began to whisper incoherently: "Too much...sensitive...but don't stop...oh, fuck...please." I dragged my tongue against her clit in long slow strokes and she hunched forward, her muscles starting to tighten again. I moaned an "Mmmhmm" of encouragement into her pussy. My chin and neck were soaked as she began to cum for a second time. She'd leaned further forward and was now all but hugging the pillow that I was laying on. Her hips bucked lightly against me and I held her tightly through this second, much more intense, orgasm.

I finally relented as she shook and whimpered over me. I released my grip, allowing her to put some distance between my face and her sex. I dragged my fingertips across her ass cheeks and leaned in to lightly kiss her wet pussy. She gasped a soft "Thank you."

I replied "My pleasure."

She smiled and said "No, I think it was definitely mine." and laughed softly.

She reached back behind her and wrapped her fingers around me. I had never really softened after leaving her mouth but, if my erection had abated at all, I was now fully hard again. "You're more than ready for more." she said.

She slid down and was laying on me again. She kissed me and tasted her sex from on and around my lips. She broke the kiss and looked me in the eyes. "How long are you alone today?" I told her that it would be another four or five hours until my mom got home and that Amanda was working all evening. She suddenly looked both serious and concerned.

"Can we spend all of that time here...together?" she asked.

"There's nothing I want more than that." I replied.

"Will you make love to me?" she asked.

"Are you sure?" I replied.

"Oh, yes. I'm absolutely sure. I want this so much." she answered.

"Then I'd love to make love to you." I smiled at her.

"Where are your condoms?" I gestured to my nightstand. She reached over and opened the drawer, extracting a condom from the box as well as grabbing the bottle of lube nearby.

She'd placed everything atop my nightstand. She picked up one of the condoms and climbed off of me before telling me to stand next to the bed.

She tore the package open and took the condom out, immediately popping it into her mouth to wet it. After removing it from between her lips, she placed it on the head of my cock and rolled it all the way out. Taking the bottle of lube, she then drizzled some of it onto my sheathed cock and spread it over the entire surface by giving me several strokes of her hand. She slid back on her ass and laid down on her back. Legs spread, she ran her lubed hand up and down the length of her wet slit and made slow, small circles atop her clit.

I kneeled between her legs and leaned down toward her. As she moved her hand away, I grasped the base of my cock and slowly slid the head up and down the length of her lips, the way she had just done with her hand. I moved my hand and then pressed myself against her...sliding the shaft of my cock up and down against her in a dry, but not at all dry, humping kind of movement. She moaned at the sensation of my cock sliding over her sensitive clit. I leaned back out and gripped myself again, pressing the head of my cock between her lips. "Please...go slowly." she implored. I kissed her softly on the lips and began pressing myself inside of her, fractions of an inch at a time, giving her a chance to adjust to me. As the whole head pushed inside of her, she moaned "Oh, fuck it's thick." I stopped and asked "Are you ok?" to which she quickly replied "Yes. It feels so good. Go slow but don't you dare stop!" I smiled and continued to slowly fill her.

She "Unhhhhed" and moaned the entire time I was sliding into her. As I finally felt my balls against her and she'd taken all of me in, I rocked back and forth against her...grinding a bit. With each movement of my hips, she uttered "Yes. Yes. Yes." as her fingertips began to dig into my shoulder blades. I began to kiss her softly but deeply as I withdrew a bit and pressed myself back into her. She moaned into my mouth and I did the same. Her pussy was so incredibly tight that I couldn't imagine anything feeling better. It was almost as though I was being given the tightest, wettest handjob imaginable. I continued moving inside of her...establishing a slow rhythm. I moved down and began to kiss her neck, grazing it with my teeth and then moving up to her ear and taking the lobe between my lips. She gasped more and more into my ear as I moved inside of her. I leaned back and looked her in the eyes as we moved together.

"Please don't stop." was all that she could articulate as her breathing intensified and I knew she was on the precipice. I kept my rhythm and intentionally began to bottom out more forcefully each time, finishing each thrust with a hard press of my hips. Her audible reactions were the sexiest thing I'd experienced in my life. "Yes. Oh, yes. Oh, I'm cumming!" she cried as she fully dug her nails into my ass and began to spasm beneath me. I maintained the same thrusting as she came, her fingers digging for purchase from my ass, up my back, across my shoulders, and finally to my head where she took up fists full of my hair. As she came, I felt a rush of wetness that soaked my balls and the insides of both of our thighs. She hadn't squirted but she had clearly cum very hard. As she panted and gasped for breath, I slowed my thrusting and stilled myself inside of her, sensing that she was just too sensitive to continue at the moment.

I couldn't have been more wrong.

No...really.

Anna looked me straight in the eye and said...

"There's one more thing I need to ask of you. It's serious and I'm very serious when I ask it." she said.

I gave her a concerned and imploring look.

"Will you fuck me? I mean...will you really fuck me?" she asked in all seriousness.

"Do you know what you mean? Do you know what you want?" I asked.

"I'm not asking for bondage or anything sadistic. It's just that...Jeff has sex with me. It's fine and I do enjoy it. But I want you to fuck me. I want to be owned. To be yours. Drive me like you stole me."

I had already sat back on my knees and she had sat up, leaning back on her hands. I just kind of stared at her. She laughed and said "You think I'm kidding." I smiled and said I wasn't sure what to think at the moment.

She turned and gathered the pillows, got up on her knees and leaned forward to hug them to her chest. Fully presented to me, she turned and looked over her shoulder. "How much more of an invitation do you need?"

My erection had been flagging a bit just because of the lack of activity but, now, it was full-on raging again. I grabbed a condom from the nightstand and quickly switched them out. Moving behind her, I positioned myself and easily began to push inside of her. She may have been incredibly tight but she was also incredibly wet. Partially in, I grabbed her hips and slowly slid the rest of the way inside of her. She moaned her approval. She'd gotten used to the size difference by now and I didn't have to be as careful. That was a good thing considering the request she'd given me.

I gripped her tightly and began to slam my cock into her as hard as I could. She wanted to be fucked and, dammit, I was going to fuck her. She was loud. Holy shit, was she loud. I was glad that our neighbor was never home. I reached up and grabbed her long, blond hair. Wrapping it around my hand, I pulled while still holding her hip with my other hand. She loved that and let me know with an "Oh, FUCK, yes!" After a few minutes of pounding her like this, I decided to change things up a bit.