Anna's First Time

 

I have a girl that works for me in my law office every Saturday. Her name is Anna. She's such a sweet innocent young girl. Saturday is the day I'm always there alone catching up from the week, while Anna does all the 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. She just turned eighteen a few weeks ago too. 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 her curvy hips are well formed to match her attractive figure. 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 dress, especially her pleated skirt. She looks like she's ready for cheerleading practice in that attire. 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 parted a bit and I would get a peek up underneath her skirt. One day she inadvertently had her legs spread a lot and I could see everything. "Pink panties," I said to myself. "What a fucking cute kid." It took a lot 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. 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 from 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 that she was reading my nasty thoughts.

So there we were just looking and staring into each other's eyes. 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." I responded breaking the silence. 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 answered. "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 sexy body even if it was just her arm.

"What were you thinking?" She asked.

"What do you mean? When?"... I questioned.

"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 suddenly 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 just sighed. I almost couldn't believe what was happening. Did she want me to keep feeling her up? I took another gamble and caressed softly across her cute ass. She didn't stop me. She just kept her eyes closed. I sensed she wanted me to continue. So I started squeezing 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 about this moment many times while watching Anna work in my office.

Her tiny rear end felt so soft as I caressed and squeezed it. Then I got a little bolder and slid my hand up underneath her skirt. Her naked legs and silky soft thighs felt incredible. They were so smooth and tender. I gradually worked my fingers between her legs and inched them higher and higher, until I was literally squeezing my hand between her inner thighs. Her flesh was so soft and warm in there too. After a short moment she responded and actually spread her legs apart without me asking. She was letting me in there. Anna was allowing me access to her pussy.

I rubbed and massaged firmly right across her cunt through her panties. I wanted her to know I wasn't just teasing and that I meant business. There was no stopping now. I had every intention of getting her turned on like I imagined 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 play with her body.

After a couple minutes of fondling her body, Anna closed her eyes and was just enjoying the feeling. Obviously, she liked my touch quite a lot. I continued stroking my fingers gently between her legs, feeling her slit through the silky material of wet panties. And they were really becoming soaked. This sweet young girl was responding to my touch.

She began making really soft moans through her breath, so I knew that I was getting her quite aroused. She became wetter and wetter. She then widened her stance to allow me a better access. I pushed her short skirt up around her waist and she held it. She sure was beautiful with those dainty sheer panties clad around that cute bottom. Then using my middle finger I started rubbing harder across the crotch of her panties to feel her slit some more. I kept stroking back and forth and her panties continued to fill up with the wetness that seeped 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 too. I wondered if she had ever experienced anything like this?

I used a little more pressure as I stroked between her legs. I could feel her clit getting harder too. Then with one finger I pushed the silky material between the folds of her cunt. Her moans became a little louder. "Ouuuuu..., Ohhhhhhhhhh." I kept massaging within the folds of her pussy and playing with her. Her clit was hardening more, as her excitement level was increasing and she was obviously getting very aroused.

Then I figured why not, let's just do it. 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, in the meantime, had unbuttoned her blouse, which amazed me that she was so willing to be naked in front of me. I helped her off with the top and then her bra, which quickly followed. She now stood there totally nude. Her cute little tits were gorgeous. "My God, I thought to myself staring at her soft full nipples jutting out from her young developing breasts. "This sexy little teen is one hot looking piece of ass."

Anna continued to stand there with her legs apart, allowing me access to her wet exposed 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 dripping pussy and sucking those nipples was making me incredibly 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 that my fingers were covered with her juices. For a few more minutes I just played with her clit and rubbed just inside her delicate pink hole.

Then I let a finger enter her, sliding it slowly through her tiny opening and up into her young body. "Ohhhhhhhhhhhhhhh!! Ohhhhhhhhhhhhhhh!!" was the only response she moaned out.

I sat Anna up on my desk and spread 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 whimpered out her enjoyment of how good it felt. When I leaned down and licked her, to taste her sweet juices, she squirmed so much that she nearly fell off the desk.

After repositioning her back on the edge, I pulled my finger out. Then I moved my hand back further, so my thumb could massage her clit, while my middle finger found her tiny little asshole. Anna let out a quick "Ohhh... Ohhh...," as my finger teased her tight virgin anus. I really enjoyed feeling the tightness and resistance of her incredibly tight puckered hole. There were so many times that I had thought of this cute ass and now here I was fingering her little butt hole. I was sure that this was the first time she's ever had anyone touching her this way.

After applying pressure a few times on her amazing back hole, I pushed a little harder and let it ease inside. That brought an immediate response from Anna. "Ouuuu..., Ohhhhhh...."

"Do you like that, Anna?" I asked.

I knew she did because she was hardly trying to stop me. At the same time I kept my thumb massaging her clit, keeping her very aroused. I knew there was no way that this sweet little thing had ever experienced anything like what I was doing to her. Her excitement was growing rapidly and I knew that I could probably take more liberties with her.

I began pushing my middle finger deeper into her ass. Her tight anal sphincter had an incredibly tight hold on my finger, as I slowly shoved it deeper into her body. I was enjoying this so much that my cock was completely erect and rock hard.

I wiggled my finger a little, letting her get a good feel of how far I was buried inside her ass. She whimpered, but made no attempt to stop me.

I pushed deeper and deeper, probing into her rectum. Anna moaned louder and longer. "Ohhhhhhhhhhhhhhhh..., Ohhhhhhhhhhhhhhhhhh..., Ouuuuuuuuuuuuuuuu..., Yessssssssssss..., Yesssssssssssssss!!!"

She was really enjoying this. I kept inserting my finger slowly into her ass, until my middle finger was fully buried inside her rectum.

"How's that feel, Anna?" I asked. "Are you enjoying my finger in there?"

She just kept moaning, so I took that as a positive response.

Then I started wiggling my finger around, sort of in circles inside her rectal cavity and she just went wild.

"Ohhhhhhh God..., Yessssssssssssssssss..., Yesssssssssssssss.... Ohhhhhhhhhhhhhhhh..."

"Does that feel good, Anna?" I asked.

Seeing her so turned on had my cock bulging, not to mention how horny I had become from all the fingering of her cunt and asshole. I removed my finger from her cute bottom and stepped in close between her legs. I dropped my trousers and underwear to the floor and grabbed my stiff cock. Then 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. I inched forward slowly and eased my stiff meat into her pussy. "Oh Anna, you're so tight," I groaned.

I pushed deeper into her tight young cunt while she held me and moaned. "Ohh..., Ohhh that's so good."

I kissed her deeply and she returned the passion with her hot tongue. She probed into my mouth like an experienced woman who knew exactly what she wanted; yet I knew she was nothing more than an inexperienced naive teenager. Needless to say though, she sure knew how to kiss.

I fucked her slow and deep, while our lips remained locked for what seemed an endless amount of time. We were devouring each other's lips and 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 young body and she was so wet. She was moaning to me constantly too.

My cock felt as though it were on fire, surrounded by her burning hot cunt. It was making me so crazy that I ripped off my shirt, so I could feel her young naked body next to mine. I reached down taking hold of my rigid shaft and eased it from her pussy. I then slipped it down and rubbed my cockhead over her asshole. I wanted to be in her ass so badly. I had daydreamed so many times about her ass that I had to have it.

I positioned my cockhead right on her puckered little hole, while at the same time breaking momentarily from our kiss. I softly whispered. "I want to put it in your ass, Anna."

She looked at me with a smile and then kissed me deeply again, while wrapping her arms tightly around my neck and shoulders. It was as if she had instantly transformed in this the young experienced teenaged woman. She didn't utter a word, but her actions were saying, "Okay, fuck my ass. I'll hold on tight. Go ahead and do me."

I pushed forward exerting pressure on her anal hole, knowing that this was her first time. I maintained an easy forward thrust, until I could feel her sphincter give way. Then it happened so quickly. My cockhead stretched her little butt hole open and I entered her ass. Her kisses intensified almost tenfold, sucking my tongue into her mouth while at the same time grunting, "Uhhh..., Uhhh..., Uhhh...,!" as her asshole spread apart for me. I drove into her with my stiff meat penetrating just a bit. She knew I wasn't going to stop there. Anna could sense that I was going to bury myself all the way up her young teenage anal channel.

She held on tight, as I started penetrating her rear orifice more. She kissed and kissed me, while I fucked into her ass. This was no longer the young girl that worked for me. This was a beautiful young teen experiencing and enjoying a sexual encounter that she had never realized existed before.

I began fucking her slow at first, sliding my engorged shaft in and out of her asshole and letting her sphincter get used to having it spread open. My cock felt so hard and stiff buried in her lovely behind.

Then as she loosened up a bit, I picked up the pace and started fucking her hard, in and out, driving my cock as deep inside her rectum as I could. I knew this was a first for her. Amazingly enough though, she was doing extremely well for her first anal fuck.

She let out a loud whimper during our deep kissing, sort of a half cry and half moan of pleasure when I hit bottom all the way inside her ass. "Oooooohhhhhhhhhuuuuuuuu,... Oouuuuuuu!"

She took a couple deep breaths. Then again, "Ohhhhh..., Ohhhhhh..., Ahhhhhhhh..., Yessssssss... Ohhhhh, Yesss..., Ohhhhhh..., Yessssss " Then her lips clamped back 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 Anna's tight rear end and seeing her intense orgasm, I just couldn't take anymore. I pulled from her cute sexy bum and helped her off the desk. She was breathing heavily. She reached for my cock, grasping it in her dainty hands and jerking it, as if to say, "My God, this thing was in my ass?"

I placed my hands on her shoulders and started pushing downward. She knew what to do. She obediently kneeled down in front me, knowing what I wanted. Looking down and seeing her gorgeous body there was such a hot sight. There was cute little Anna, naked, holding my stiff dirty cock.

I asked. "Have you ever sucked a cock?"