Breaking in Anita Ch. 05

Chapter 5: A sexy massage

This is the fifth 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 4 first, as it gives context to the somewhat peculiar carnal relationship that will continue to unfold.

I regularly give my wife a massage, and over the years, I think I have more or less perfected my technique. It usually starts out as a therapeutic sports massage, especially after hard exercise, but invariably leads to delicious sex. About two weeks ago, and whilst giving my wife a massage, I suddenly remembered how my venture into massage sex had started, more than 30 years ago.

As with many firsts in my sex life, it started with Anita...

One Saturday morning, grocery shopping at the mall, I walked past one of tho se little shops in the middle of the aisle, this one selling different kinds of fragrant soaps, incense and oils. I had time to spare since it was a miserable cold and rainy day outside (no sports), and since Anita was only coming over for dinner that evening, I had all afternoon to buy and prepare food. I browsed the shelves at my leisure, smelling different soaps and oils. I stopped at one shelf marked "Massage Oils" and spent some time sniffing the different products on offer. I have been for therapeutic massages as part of rehabilitation after sports injuries, and found those painful, but quite effective in the long run. Quite a few times, I've had massages just to relax, and found those very enjoyable. I particularly remember one time - after a bicycle race, I went for a leg massage to soothe my aching muscles at our local sports center. A very attractive young physio was assigned to me, and although I usually ask for a deep tissue massage, that time I felt a little naughty and told her I just wanted a "relaxing massage". Maybe it was just my dirty mind, or maybe the physio was coming on to me a bit, but I found it very erotic, especially when she rubbed and kneaded my backside and upper legs, stopping just short of indecency. I could not help myself but fantasize about a "happy ending" massage with her. After the massage, I had to take my time to put my shoes on, as it took a while for my semi-erection to subside.

One label on the shelf in this little pop-up shop caught my eye: "Sensual Massage Oil - with lavender and Ylang Ylang Oil" it read. I opened a sample bottle to smell, and the sweet smell caught my olfactory nerves as somewhat erotic. Immediately, an idea sprang to mind: Anita was coming over that night, and with a bottle of massage oil and a bottle of wine, things could develop...

I made the purchase, adding a bottle of fragrant lavender bath bubbles, and rushed through the rest of my shopping in order to get home. I hit my laptop, searching for "Erotic Massage" and "Sexy Massage". I found quite a few NSFW videos and I browsed through them, picking up tips and tricks. One actress, called Sybil A. or Kailena, a girl from Ukraine, reminded me of Anita a lot, and I watched the video from beginning to end. I was so absorbed in the massage videos that I almost forgot about the food, and by 5pm I had to rush to get everything prepared and jump through the shower before Anita arrived.

As usual, she arrived promptly on the arranged hour, and the food was just about ready. It was a cold day, and Anita was dressed in a bulky puffer jacket, tight fitting leggings and short boots. Despite the bulky outfit, she looked stunning. My apartment had central heating, and she soon got rid of the jacket, revealing a tight white t-shirt which showed off her breasts perfectly. At dinner, she remarked casually "So, I received no text message with instructions for tonight?"

"No," I said, "but I do have something prepared for you however." "After dinner, I want you to take a nice hot bath, and I'll be ready in the bedroom when you're done". With a sparkle of anticipation, she said "Mmmmh, sounds promising!"

We finished our wine, and while Anita was drawing a bath, I cleared the table, and took a glass of sparkling wine to the bathroom. She was just getting into the bath filled with foam, and I handed her the glass, saying "Bubbly to go with the bubbles. Give me five minutes".

In the bedroom, I lit five candles standing in different tables around the room, spread a large beach towel on the bed in case things got messy, and thoughtfully put a large pillow under the towel to lift her backside. When Anita came out of the bathroom soon after, I was lounging on the bed, sipping on my glass of sparkling wine, wearing only a bath gown. She walked over, and gave me a kiss. I picked up the bottle of massage oil from the bedside table, and showed it to her. "Mmmh. Niice!"

I moved over, and patted on the beach towel. "On your stomach to start with" I instructed, and she dropped the towel. She draped her lithe body over the pillow, positioning herself just right, so her ass was higher than the rest of her body. I poured some oil into my hand to heat it, applying it liberally over her back. I started off innocently enough, thoroughly massaging her neck and shoulders, although it was impossible to look at her protruding buttocks to my right. She was lying with her right cheek on the pillow, eyes closed, but every now and again she would lift one eyelid to look at me with a big brown eye and a "Mmmm, yes".

Having spent a good five minutes on her back and shoulders, I took a big handful of oil, and spread it over her buttocks and upper legs. I took the bottle, and drizzled some in her cleft, knowing that the cold oil would run down to her pussy. She gave a little shiver, and I could see goosebumps on her but cheeks, but she did not complain. I spent some time massaging her upper legs, and made sure that every time, I would remove my hands just before I reached her lady bits. I then started kneading her buttocks, marveling in the softness of her smooth skin, and the lighter colour of her glutes that her bikini bottoms left in contrast to the dark tan on her back and legs. I knew by now that she had a sensitive spot right at her tail bone, just where her cleft started, and made sure I teased her properly by in turn rubbing the spot with my fingertips before scratching it lightly with my nails.

Anita moved her legs slightly more apart, and I reached my fingers into her cleft, rubbing the inside of each buttock, and lightly touching her butthole each time my fingers slid over it. I resumed my attention on her upper legs, lightly rubbing the inside of each leg from the knee upwards, but taking care now not to miss her pussy. On each stroke, I would end by turning my hand and lightly stroking her labia from the towel upwards to her perinium. She spaced her legs even wider, and arched her back, allowing her pudendum to lift slightly from the towel, and allowing my right hand to reach her clitoris. I put my left hand on her buttock, with my middle finger right on her anus, and reached down with my right hand, circling her clit a few times, and then rubbing between her pussy lips right up to the perinium.

Gradually, I increased the pressure of my left middle finger on her butt ring, and slowly slid in the first knuckle. Anita was highly aroused, and pushed her butt higher, allowing me to slide in another well-oiled knuckle. I moved down slightly on the bed, turned my right hand around, the palm of my hand facing her feet, and inserted my middle finger into the warm folds of her pussy. I reached down with my finger, and found her G-spot, well swollen already. She gave a low moan when I gave the G-spot a little rub, and pressed it lightly against her pubic bone. I pulled out my finger, and instead inserted right thumb into her pussy, and removed my left middle finger from her butthole. I instead inserted my right middle finger into her ass, as far as I could, and brought my two fingertips together like somebody grabbing a six-pack of beer. My fingers could almost touch each other, had it not been for the tissue and muscle between her vagina and rectum. I gave the separating wall a little rub and a squeeze, causing both the vagina and anus to stretch in a way it was not accustomed to, causing Anita to groan. I removed my hand, and told her "Flip over - other side".

While she was rolling over, moved back to the middle of the bed, and I wiped the fingers that explored her anus on the beach towel. I could not see any fecal matter on either, but knowing that she probably did not rinse in preparation for this unexpected intrusion, I did not want any unpleasant surprises. I put a few drops of oil on either breast, causing her areolas to contract, and the tubercles around each nipple to form goosebumps. I put a good squirt of oil on her clitoris, and gave it a good spread around. With my left hand, I massaged her breasts, and at the same time, used my right to rub up and down between her labia, stopping at the clit to give it a few good circular rubs before continuing the middle finger's traverse of the slit.

Anita opened her eyes, and put her hand around my cock, which had by now cheekily worked itself free from my gown and was pointing at the ceiling. Anita used her thumb, and rubbed the drop of pre-cum around the tip of my penis. She curled forward, and leaned in to undo the knot in the belt of my gown, twisting her body to get her mouth onto my cock. She put her warm lips around the glans, and sucked hard, getting about a third of my shaft into her mouth. Pleasurable as it was, we could not hold this position for long, as I had to twist my torso to keep my hand between her legs. I removed my right hand, and she looked up at me. I gave her a kiss on the mouth, and said "You go on top".

Anita stood on her knees, making room for me on the towel. I put my backside on the pillow in the middle and she straddled me, using her hand to guide my cock into her pussy. She slowly lowered herself onto my shaft, giving me a lovely view of her breasts glimmering with oil, and her leg muscles contracting as she slowly lifted herself up again. I reached up, and rubbed her breasts again, rolling each nipple between my thumb and forefinger and then squeezing and pulling on them, causing the oily nipples to pop out between my fingers. If pleasurable for me, it was clear that Anita enjoyed this even more. She looked at me through lowered eyelids, and each time I made a nipple go pop, her eyes appeared to roll backwards, and I could only see the whites of her eyes.

She put her hands on my shoulders, and leaned forward, kissing me. She started with little butterfly kisses, alternating between my upper and lower lips, with a little pointy tongue darting in and out of my mouth every now and again. I pulled her left leg up next to my ribcage, and wriggled my right hand in under her leg to find her clit. I used my middle finger to rub her clit, with my thumb and index finger gently massaging her buttock. Anita was stationary, allowing me to access her clit, and I resumed the fucking with little hip movements. The feeling was exquisite - her nipples were rubbing against my chest, and I could feel my rock-hard cock rubbing against my fingers as I continued the somewhat awkward massage. Anita's kisses were becoming more insistent, and she pressed her body closer to mine, causing my hand to lose contact with her little pleasure button. I removed my hand, and Anita started slithering her slippery body up and down, never letting my cock slip out.

I reached around her left buttock, and slipped my middle finger into her butthole, up to the second knuckle. Through the dividing tissue, I could feel my cock sliding inside her vagina, and twisted my hand, increasing the pressure of my cock against her vaginal wall. Two or three more strokes was all it took to push her over the edge. Her body shuddered, and she exhaled deeply, emitting her trademark low animal growl. I was close behind her, and took both hands, lifting her slightly from my pelvis, and finished with another seven or eight sharp strokes, with my hips slapping against her oiled buttocks. As I came in long spurts deep inside her, she pushed back on my cock, as though she wanted to swallow me with her lower body. Anita relaxed her slim body on top of me, and we must have laid there for a good five minutes, breathing in each other's presence. Gradually my cock went flaccid inside her, and when it plopped out, I could feel my semen running from her pussy onto my cock, down my scrotum and onto the towel.

"Niice..." Anita said before getting up to go to the bathroom.

And that, dear reader, is how it started.