Breaking in Anita Ch. 04

Chapter 4: ANAL

This is the fourth chapter in this series, and although it is a stand-alone story that can be enjoyed on its own, you may want to read Chapters 1 to 3 first, as it gives context to the somewhat peculiar carnal relationship that will continue to unfold.

Given the weekend's very satisfactory (and satisfying) exchange of cunnilingus and fellatio, I decided that I should not let things go cold, and that it was time for the next step. Before our previous liaison ended (see Chapter 2), I would often put a finger up Anita' ass while she was riding me astride. She never complained or resisted this, and in fact seemed to quite enjoy it, but given her resistance to giving or receiving head, I never thought to go all the way to proper anal sex, and from experience with previous girlfriends, I realised that this would be a big hurdle to get over.

Now, with her unconditional "Yes"-promise, I thought that it should be a natural progression of this new phase of our friends with benefits relationship. Even so, I was concerned that it could be too much too soon, and kept putting off the suggestion.

I celebrated my twenty-ninth birthday on the Wednesday after the weekend, but apart from a few drinks after work with colleagues, I did not have anything planned. I did not think that Anita knew when my birthday was, and did not plan to tell her, because I wanted our relationship to be purely platonic, although sexual, and did not want to risk any emotions creeping into this. I'm not anti-birthday as such, but twenty-nine really did not mean much to me, and I was quite happy to let it glide by, at least as far as Anita was concerned.

However, I had forgotten about Anita's friendship with my tattle-tale sister Amy (see Chapter 1). When I came into the office after lunch on Wednesday to find a bunch of assorted flowers on my secretary's desk, I teased Tania by saying "Aah, new boyfriend?" as I walked past, but she surprised me by telling me, "No, these are for you!" There was a little plastic fork in the middle of the flowers with a plain white cardboard that read: "Happy Twenty-ninth, Brian! Can't wait for the next yes. Yours, YFWB". This was Tania's turn to tease and ask who "A" is, and whether "YFWB" meant what she thought it did. I played dumb, as I really did not want this relationship with Anita become public knowledge. Although we live in a big city, the legal fraternity is quite small, and the story of the stunner that I have been seen with has already made its rounds amongst my ever-gossiping colleagues.

I took the flowers into my office, and sat at my desk, in turn looking at the flowers and re-reading the card. I've never received flowers from a girl in my life, and have never heard of any woman giving a man flowers. This girl was clearly cut from a different cloth, but she obviously tried to do something out of the ordinary whilst respecting the borders we had both agreed to. Had she given me a bunch of red roses or carnations, I may have been disturbed because that could have signaled the forbidden L-word, but a bunch of assorted flowers is just a nice (if unusual) gift between two friends with benefits. The card was clear however: she was looking forward to the next yes, and it was up to me to ask.

By Thursday morning, I made up my mind. I decided to go for blow, and sent a text to Anita, this time not as formal and legalistic as my previous note (I thought a personal touch might be more appropriate, given the next level of intimacy I had in mind): "Hi, thanks for the flowers! I look forward to the next yes too. I know you have a free weekend. Friday night is anal night. Be ready. See you at 7; same place, same time. We can order pizza after. YFWB".

I did not receive the same "Yes" text as before, and was a little anxious - had I gone too far now, and has the pony bolted in fright? Even so, I was quietly confident that things may come together. During lunchtime on Friday, I went to a pharmacy, and bought an enema because I knew from my healthy interest in pornography that anal could be messy if the girl was not properly cleaned. Fortunately, the pharmacist is a friend of mine, and when I told him why I needed the syringe, he gave me sound advice - three rinses should be enough, and a teaspoon of unscented coconut oil in the water will help with lubrication as well.

I was a little worried that the rinsing procedure before actual anal sex might put Anita off the whole thing, but with my analytic legal mind, I made a list of pros: 1) she seemed to like a finger in her butt before, 2) she gave me an unconditional promise of "Yes", not only when she wanted to come back to me, but again on my birthday card, and 3) she knew what is coming, and if she's at my apartment, it will be one small step ...

I took a shower and changed my clothes before leaving work, and drove home with a good dose of anticipation, mixed with a little trepidation. I arrived just after seven, only to find my apartment engulfed in darkness. "Shit" I thought, "she's gotten cold feet". I switched on the passage light and put my car keys in the crystal ice bucket on the hallway table. There was a little white card in the bottom of the bucket that simply read "Bedroom" in neat cursive female handwriting. I turned off the light and proceeded to the bedroom, chucking my suit jacket on the chair in the little hallway between the bedrooms. I could see candle light flickering in the bedroom, and when I turned the corner, there was Anita: completely naked, on all fours in the middle of the bed, with her backside sticking up in the air. She turned around, looked at me, and with a sultry voice whispered "It's 'yes'".

I smiled like a cat looking at a bowl of cream, but realised that we still had the rinsing bit to attend to. I sat down on the bed and said "I'm really pleased, but there is a little technical detail - would you mind if we cleaned you up first?". I held up the paper bag from the pharmacy. She gave me a sly smile and asked "Enema with a little oil?". When I confirmed that this is what I had in mind, she said "Done. Four times - you said I should be prepared, and I told you I knew how to Google!"

To say that I was impressed, would not be an exaggeration; not only was this girl willing to submit, but she was fully prepared and ready for action! In two seconds, I was out of my clothes and sitting cross-legged behind her, a butt-cheek in each hand. I marveled again at the smoothness of her skin and gave the inside of each silky buttock a long lick to show my appreciation. Beneath her little butthole, the pussy lips stretched downwards. Although anal was to be the course du jour, I could not resist giving her slit a long luscious lick, and put my right hand between her legs to give her clit a little firm massage where it was still hidden under its hood. I edged in closer put my left hand around her left thigh to continue the clit massage, and bent closer to breathe in the smell of her protruding backside.

There was a distinct smell of coconut oil between her butt cheeks, and from the glistening skin around her anus, I could tell that she was properly lubricated. I gave her butthole a little flick of the tongue, just for good measure. She arched her back, and put the left side of her face down on the bed, pushing her butt even higher. I decided that it was time to introduce a finger, but the angle of my left arm around her left thigh made it uncomfortable, so I told her "Take one hand and play with your pussy". She obliged by taking her right arm from underneath her head to start her own pussy pleasure, leaving me free to put the first digit of my middle finger in her asshole. It went in very smoothly, and with the lubing she did before, I could have slid in the whole finger at once.

Slowly, Brian, slowly, I admonished myself as I gently pushed the first digit in and out of her anus. Her butthole was not only as tight as I remembered, but as I slowly moved my finger in and out, the muscle clenched and unclenched, gripping and releasing my finger in turn. I slid in the second digit, and moved the tip of my finger around her sphincter, exploring the folds inside. I could hear Anita groaning into the mattress, whether from the anal stimulation, or her own hand on her pussy, I did not know, and did not really care. All I knew was that I had a gorgeous young woman on my bed, allowing me to do what I want, and enjoying herself while doing so.

My cock is a little bigger than normal, and I knew I had to get her tight little butthole a little wider to accommodate me. I slid in my index finger as well, and to my surprise it went in fairly easily. The butthole was as tight around my fingers as it was before, but I could move my fingers in and out with relative ease. I could sense Anita's little hand busy with her pussy, and her moans growing even louder. My cock was as hard as it has ever been, and I could feel the precum running down my tummy where the tip was pressing. When I asked whether she was ready, Anita replied with what was by now my favorite word: "Yes".

I positioned myself behind her, and taking my shaft in my right hand, intending to slide it up and down between her wet pussy lips a few times to get the lubrication going properly, but could not resist putting it in her vagina for a few strokes. All the time, I could feel Anita's hand rubbing her clit, and her moans becoming longer and more husky. I positioned the tip of my cock against the butthole which a minute ago swallowed two fingers, and pushed forward, but found that it was closed shut.

I felt that we needed more lube, but realised that I would have to get off the bed, look for the pharmacist's bag in the half-darkened room, open it and find the coconut oil. I did not even know what the oil looked like or whether it would be in a box that needed to be opened again, and sighed "I need lube!" before withdrawing from the enticing target that was on full display. Ever the prepared little minx, Anita said "Here" before reaching under the pillow and handing me a tube of coconut oil. With a little squeeze in and around her butthole, and another squeeze on the head of my cock, we were ready for the second take. I pressed my cock against the knotted little muscle, and felt Anita push back in turn. As if by magic, the head slipped in, and we gave a simultaneous groan. I could feel her anus gripping and loosening around my cock as I slowly pushed in and out in little strokes. I knew that this had to advance slowly, but Anita was having none of this. I could feel her nails against my smooth scrotum as she was pleasuring her pussy, and she kept pushing back harder and harder, swallowing my cock in her tight butthole little by little.

Waves of pleasure ripped through my body, and I realised that I would not last long before coming. The stimulation caused by the tight little butthole was four, five or six times more intense than any vagina. Most of my cock was inside her, and the clenching and unclenching of her butthole was becoming unbearable. I started moving in and out of her anus, slowly at first, but then at ever increasing speed, with Anita meeting my strokes by pushing back in perfect rhythm. My hips slapped against her firm buttocks and this sound, together with Anita's moans tipped me over the edge. I pushed forward with one final hard stroke, pushing her off her knees, and we both tumbled face down into the pillows with me squirting like a fountain inside her. As I was coming, I could feel her butthole clenching and unclenching around the shaft as if she wanted to milk it to the last drop, causing my cock to twitch inside her and donate the last bit of semen deep inside her.

Afterwards, eating pizza and drinking wine by candlelight, Anita told me that she did not achieve one great orgasm as she usually did, but a series of small ones (or as she called it "little shweez shweezes"). She assured me, however, that with practice, we will get it right.

Always something to look forward to with this one!