Annas First Time

I have a girl that works for me in my law office every Saturday. Her name is Anna. She’s such a delight, a sweet innocent young girl. Saturday is the day I’m always there alone catching up from the week while Anna does all my filing for me. Anna is really quite a cute little girl; at least that’s the way I see her. She’s about 5′ 7″ tall and very, very slender. I figure she only weighs about 100 pounds. Anna just turned eighteen a few weeks ago, but you’d never guess that. She looks like she’s only 14 or 15 years old. Maybe that’s what makes her so exciting to me. She’s got a great body with small breasts maybe only a 30 or 32 inch chest. Her waist is very thin perhaps 22 inches if that, and hips matching her attractive figure. But then there’s Anna’s rear end. Yes, her ass. Her ass is what always catches my attention. Many Saturday afternoons I’ve stared at her while she was filing and just gazed at her well-proportioned bottom.

I always loved those days when Anna would wear a blouse and a short skirt, especially her pleated skirt. When she wears that, she looks like she’s ready for cheerleading practice. Needless to say I have a hard time concentrating on my work those days. I would spend most of my time watching Anna and those smooth slender legs. Every time she bent down and her skirt rode up higher, I’d catch a glimpse of her soft supple thighs.

“My God,” I would think. “Look at those gorgeous legs.” You talk about driving a man nuts; well this is what was happening to me. Sometimes when she sat at the table next to my desk her legs would be apart a bit and I would get a peek up underneath her skirt. One day she inadvertently had her legs spread allot and I could see everything. “Pink panties,’ I said to myself. “What a fucking cute kid.” It took allot of willpower to keep from grabbing her and feeling her up.

Anna is a very proper young lady always being quite polite and appreciative of having a job and working for me. Although I’ve daydreamed many times of having a go at her petite gorgeous body, I never really thought anything more of it or that anything could happen because she always acted so professional. She did her work, went home and that was that.

Well this one Saturday everything was normal. Anna was filing some papers bending down to the bottom drawer and I was staring at her cute ass as I usually did. And she had on that pleated skirt. I must have been daydreaming more than usual looking up her dress, because the next thing I realized was Anna staring right back at me. At first I was a little embarrassed for being caught staring at her, but she just smiled and looked back at me. However, what started out as a simple glance at each other soon became a long inviting stare. I was wondering what she was thinking and I was convinced she was thinking about my nasty thoughts.

So there we were just looking and looking at each other. She was only a few feet from me, so to break the moment I stood up and moved right in front of her. “Sorry, Anna. I didn’t mean to stare.” Well, that was a lie, but I didn’t know what else to say.

“You think I’m pretty?” She asked.

That was a silly question, I thought to myself. But I answered, “of course I do. You’re very pretty.”

“Don’t you think I’m a little skinny?” She replied back.

“Not at all,” I replied. “You’re very pretty, Anna.” I slowly brushed my fingers down the length of her arm in a reassuring way. “Very pretty.” She just stood there listening and watching me. I ran my hand down her arm a second time with more pressure. Actually I wanted to get a better feel of her.

“What were you thinking?” She asked.

“What do you mean? When…” I asked.

“When you were looking at me.” She answered back.

This was getting a little uncomfortable. So I answered her honestly.

“I was admiring how pretty you are. And…I don’t think you want to know what else.”

“Well what else were you thinking about?” She inquired looking a bit puzzled. There was just a slight moment of silence before Anna figured it out. “Ohh.. I think I know.”

“You think I’m that pretty.” Anna reached out touching my arm with a big smile on her face. I don’t know how I got so bold but I reached out to her and touched her thigh through her skirt. She closed her eyes momentarily and sighed a whisper, “that feels so nice touching me like that.” I almost couldn’t believe what was happening. Did she want me to keep touching her? I caressed softly across her cute ass. She didn’t stop me. She just kept her eyes closed. I sensed she didn’t want me to stop. So I continued feeling up her tight rear end. “You’re so pretty, Anna.” I whispered. She opened her eyes and just smiled again.

I know I was twice her age and she was really just an innocent young girl, but after having gone this far I wasn’t about to stop. This was like a dream come true. I fantasized this moment many times watching Anna work in my office.

Her tiny ass felt so soft as I caressed and squeezed her. Then I got a little bolder and pushed my hand up underneath her skirt. I felt her legs and ran my hand up her silky soft thighs. Oh how they felt so smooth and tender. I gradually worked my fingers between her legs and inched them higher and higher. With her legs together I first had to gently squeeze my hand between her thighs. Her flesh was so soft and warm in there. But after a short moment she actually spread her legs apart a little without me asking. She was letting me in there. Anna was letting me have access between her legs.

I rubbed and massaged her firmly right across her cunt through her panties. I wanted her to know I wasn’t just teasing her but that I meant business. There was no stopping now. I had every intention of getting her turned on like she’s never been before. She took a deep breath and sighed, “oh that feels so good.” I moved back to my desk sitting down in the chair with Anna standing right in front of me. She just stood there letting me feel her body.

After a couple minutes she closed her eyes and was just enjoying the feeling. Obviously, she liked my touch quite allot. I continued using my fingers between her legs feeling her slit through her soaked panties. And they were really getting wet. This sweet young girl was responding to my touch. I rubbed her softly and gently stroking my fingers between her legs feeling her through the thin silky material. She began making really soft moans through her breath. I knew that I was getting her quite aroused. She became wetter and wetter. She widened her stance allowing me a better access between her legs. I pushed her short skirt up around her waist and she held it up. She sure was beautiful with those silky dainty panties clad around that cute body. Using my middle finger I started rubbing across her panties feeling her slit once more. Back and forth I kept feeling her as her panties continued to fill up with wetness seeping from her delicate young cunt.

“Ohh, God, that’s feels so good.” She moaned out. I kept massaging her soaked panties. She was getting weak in the knees. I wondered if she ever experienced anything like this?

I used a little more pressure as I stroked between her legs. I could feel her clit getting harder. Then with one finger I pushed the silky material between the folds of her cunt. Her moans became a little louder. “Ouuuuu, Ohhhhhh.” I kept massaging her between the folds of her cunt playing with her. I could feel her clit harden more as she became more and more aroused.

Then I gently began pulling her panties down her slim smooth legs until I had them completely off. I unsnapped her skirt too and let it drop to the floor. Anna had unbuttoned her blouse so I helped her off with that and her bra followed. She stood there totally naked now. Her cute little tits were gorgeous with these full soft nipples. As Anna stood there with legs apart allowing me access to her wet cunt, I started stroking her again while at the same time kissing and sucking on her soft tender nipples. They felt so nice in my mouth. The combination of feeling her young wet cunt and sucking those nipples was making me so horny. I wanted my cock inside her so bad, but I knew how much she was enjoying my touch and I didn’t want to lose the moment. She was so wet my fingers immediately were soaked in her juices. For a few minutes I just played with her clit and rubbed her just inside her delicate pink cunt. Then I let a finger enter her, sliding it slowly through her tiny slit and pushed up into her young body. “Ohhhhhhhhhhhhhhh Ohhhhhhhhhhhhhhh” was the only response she made.

I sat her up on my desk spreading her legs. She watched me as I finger fucked her hole. She watched it disappear deeper and deeper up inside her body and each time whimpering out a moan of enjoyment. When I leaned down and licked her tasting her sweet juices, she squirmed so much she nearly fell off my desk.

After repositioning her back on the desk, I pulled my finger out then moved my hand further back to allow my thumb to massage her clit while my middle finger found her asshole. Anna let out a quick “Ohhh Ohhh” as my middle finger teased her virgin anus. I really loved feeling the tightness and resistance of her tight puckered hole. There were so many times I thought of this cute ass and now here I was fingering her little butt hole. I was sure this was the first time she’s ever felt anything like this.

After applying pressure a few times on her asshole I pushed a little harder and let it ease inside her. That brought an immediate response, “Ouuuu, Ohhhhhh. You like that, Anna?” I asked. I knew she did. She was hardly trying to stop me. At the same time I kept my thumb massaging her clit keeping Anna very aroused. I knew there was no way this sweet little thing had ever experienced anything like what I was doing to her. Her excitement was growing rapidly and I knew I could take more liberties with her. I began pushing my middle finger into her ass deeper. Her tight anal sphincter had an incredibly tight hold on my finger as I slowly entered deeper into her body. I was enjoying this so much that my cock was completely stiff and rock hard. I wiggled my finger a little letting her get a good feel of how far I was inside her asshole. I pushed deeper and deeper, probing into her rectum and she moaned louder and longer. “Ohhhhhhhhhhhhhhhh, Ohhhhhhhhhhhhhhhhhh, Ouuuuuuuuuuuuuuuu. Yessssssssssss, Yesssssssssssssss.”

She was really enjoying this. I kept inserting my finger slowly up her ass, deeper and deeper until my middle finger was fully buried inside her rectum. “How’s that feel, Anna? Are you enjoying my finger up your ass?”

She just kept moaning. So I started wiggling my finger around, sort of in circles inside her and she just went wild.

“Does that feel good, Anna?”

“Ohhhhhhh God, Yessssssssssssssssss, Yesssssssssssssss.” “Ohhhhhhhhhhhhhhhh.””Ouuuuuuuuuuuuuuuuu!”

Seeing her so turned on was had my cock bulging. Not to mention how horny I was from all that fingering of her cunt and asshole. I removed my fingers from her and moved in close between her legs. I dropped my trousers and underwear to the floor and grabbed my stiff cock. I placed it at the entrance to her sweet wet pussy. This was it. I just had to fuck her. Anna put her arms around my neck knowing what I was going to do to her. I inched forward slowly and eased my hard cock into her. “Oh, Anna, you’re so tight.” I pushed deeper into her tight young cunt while she held me moaning, “Ohh, ohhh that’s so good.” I kissed her deeply and she returned the passion with her hot tongue in my mouth.

I fucked her slow and deep as we stayed lock in an endless kiss. We were devouring each other’s lips. Our tongues were entwined, as our sexual appetite for each other grew stronger and stronger. I kept thinking to myself how this was so unbelievable. I was fucking this young kid. My cock was inside her delicate body. She was so wet. She was moaning to me. My cock was so warm surrounded by her burning hot cunt.

I ripped off my shirt so I could feel her young naked body next to mine. I reached down taking hold of my hard cock as I eased it from her cunt. I slipped it down rubbing my cockhead over her asshole. I wanted to be in her ass. I daydreamed so many times about her ass that I had to have it. I positioned it right on her puckered little hole as I broke momentarily from our kiss to tell her, “I want to put it in your ass, Anna.” She looked at me with a smile then kissed me so deeply again while wrapping her arms tightly around my neck and shoulders. It was as if she transformed in this the young teenage woman and by her actions she was saying, “okay, fuck my ass. I’ll hold on tight, go ahead and do me.”

I pushed forward exerting pressure on her anal hole. I maintained pushing harder until I could feel her asshole give way and my cock enter her ass. Her kisses intensified sucking my tongue into her mouth while at the same time she softly grunted,”Ummm!” as her asshole spread open for me. I drove into her with my hard cock penetrating a little deeper up her young teenage anal hole. She held on so tight as I started penetrating her ass more. She kissed and kissed me while I fucked her ass. This was no longer the young girl that worked for me. This was a beautiful young woman experiencing and enjoying a sexual encounter that she never realized existed before.

My cock was so hard and stiff buried up her ass. I began fucking her slow at first sliding my cock in and out of her asshole letting her anal sphincter get used to my cock. Then as she loosened up a bit I picked up the pace fucking her hard, in and out, driving my cock deep inside her rectum, over and over. I knew this was a first for her, but she was doing real good taking this anal fucking.

She let out a loud whimper through our kissing, sort of a half cry and half moan of pleasure when I hit bottom all the way inside her ass. “Oooooohhhhhhhhhuuuuuuuuiiiiiiiieeeeeeeeee!” She took a couple deep breaths. Then again, “Ohhhhh, Ohhhhhh, Ahhhhhhhh, Yessssssss Ohhhhh, yesss Ohhhhhh. yessssss ” Then her lips clamped on mine again. She was cumming. She was having an orgasm with my cock in her ass.

After a few minutes of my cock sliding in and out of her tight rear hole, and seeing Anna’s intense orgasm, I just couldn’t take anymore. I pulled from her and helped her off the desk. She was breathing heavily. She reached for my cock grasping it in her dainty hands and feeling it as if to say, “my God this thing was in my ass?” I placed my hands on her shoulders I started pushing downward. She knew what to do. She obediently kneeled down in front me. Looking down seeing her there was such a hot sight. There was cute little Anna, naked, holding my stiff cock. I asked, “have you ever sucked a cock?” She responded, “No.” Then she put her lips to my cock. She opened her mouth delicately sucking me in.

“Oh, Anna, suck me.” I moaned to her.

She was incredible. Her lips were so soft and warm. When her tongue touched the tip of my cock I thought I would lose it right then. I moved forward slightly so she would know I wanted her to take more into her mouth. “Take it, Anna. Take me in your mouth.” She was so willing. As I pushed forward, she let my hard cock through her lips and into her mouth. My stiffness slid across her tongue. My God what a sexy hot mouth she has. Her tongue began licking me, swirling around my hard cock as it traveled back to the entrance of her throat. Her tongue was amazing what she was doing to me.

Then as I wondered what she was thinking tasting my cock. Afterall I had just fucked her ass. She didn’t seem to mind or have any reaction. She just slurped away licking my shaft.

Then it happened so quickly. The sexual feeling building within me climaxed, and my cock just burst, flooding her mouth with cum. First one big spurt shooting through her lips into her mouth. Then another and another coating her tongue completely. I had three more short spasms that ejaculated more little globs of sperm into her. When I was finished Anna’s mouth was loaded with my cum. I knelt beside her caressing her soft cheek and looking at the full load in her mouth.

“Go ahead, Anna, eat it. Swallow my cum.” I watched her as she looked at me. I cradled her face in my hands delicately to show her how much I loved what she just did. I looked at her with an expression of complete gratification as I whispered tenderly to her. “Oh, swallow it. Swallow my cum, Anna.” Then her lips closed and I saw her throat move. She swallowed. My warm creamy sperm was now flowing down her throat. What a turn on seeing this cute little angel eat my cum. Then she softly took the tip of my cock between her lips and gently sucked the last little bit out of me.

After that Saturday everything changed. No longer did I see my cute Anna as a little nice sweet innocent girl. Every weekend now we fuck and suck. Saturday has become my favorite day to work.