It was a quiet Sunday morning, Sherry and I lounging in bed. Sunshine poured lazily through the curtains. I was doing one of my favorite things - touching Sherry. My fingers slid over her soft, warm skin, traveling from the soles of her feet, up along her calves and the backs of her things, up over the wonderfully rounded mounds of her rear, up along her back to her shoulders and neck, and then the delightful journey back again. I hadn't applied any the scented massage oil yet. Sherry rolled her hips and her legs parted just enough for my fingers to graze along her inner thighs. I slid further down the bed and lifted one of her feet to my mouth. I kissed the sole, then nuzzled her toes with my lips. I finally ran my tongue along the underside of the foot, then repeated the process with Sherry's other foot. I heard her emit a soft purring sound in her throat. Sherry always said that her feet were a primary erogenous zone. My lips and tongue made their slow, loving way up the backs of her legs, paying especial attention to the delicate hollows behind her knees.
I kissed and licked my way to the top of her legs, then settled myself between her thighs and lifted Sherry's hips off the bed. Presented just a few inches from my face was the wonderful sight of her pussy and ass. I moved forward and pressed my lips against her, my tongue snaking out to caress the soft flesh and probe into her delicious cleft. Although oral play was a regular part of our lovemaking, it was not usually from this angle and it heightened my sense of enveloping myself into her moisture and scent. My tongue slid down to seek out her clit, nestled between the fleshy folds of her pussy lips. I brought my tongue up an inch further, slipping into her warm, wet cavern. Sherry's juices flowed over my tongue. I slid my tongue up still further, caressing all of her cunt. And up another inch along the valley between the globes of her sweet ass. And softly quickly the tip of my tongue swept over the tight pucker of her anus.
I repeated my explorations - clit, cunt, and then back to the hidden hole, probing a little more firmly, dragging the tip of my tongue across once, twice. I felt Sherry shift her hips slightly, neither withdrawing from my touch nor pressing tighter against me. "Do you mind if I do that?" I asked, emphasizing my words by again softly tonguing her anus. "I won't do it if you aren't comfortable with it."
"No, it feels good. It's just that ... no-one ever has ..."
I swirled my tongue in a circle around the clenched ring of flesh. "You've never experimented anally? Would you like to?" I slid my tongue down to caress her clit.
"Yes, but ... I'm afraid it will hurt."
"Sherry, you'll be in control. If I start to do anything that you think hurts, anything you're uncomfortable with, you just tell me to stop. I'll take everything very slowly and gently."
"Okay."
I slid two firm pillows under Sherry's hips to give her support. I had wondered if maybe it would be better for her to lie on her back so she could see what was happening, but I decided that having her butt in the air would let me be more controlled and careful in my movements. And, besides, I had to admit to myself, looking at Sherry's up thrust ass was tremendously exciting.
Alternately licking her pussy and her anus, I started again, not wanting to bring her to orgasm, but keeping her in a state of arousal. Gradually I increased the motion of my index finger around her asshole, pressing more firmly but as yet making no effort to insert it. I encouraged Sherry to relax her muscles as much as possible. When I felt the time was right, I poured a generous amount of oil on her wonderful ass and began to massage her buttocks, taking care to stroke along the cleavage between the cheeks. My index finger and her anus now glistening with oil, I resume my circling of the puckered hole, while with my other hand I massaged Sherry's pussy. Slowly, steadily I slid my finger inside the circle of muscle. There was less resistance than I had anticipated, although I did feel the ring contract slightly, then relax again. I slid my finger partially out, then back in again, setting up a slow rhythm while working more oil into her asshole. "You look sexy," I told her. My cock ached, but I restrained myself from any sudden action.. After several minutes, I replaced my index finger with my thumb. Sherry rotated her hips slightly, not with discomfort, I understood, but with a pleasured reaction to the increased sensation.
I moved my hips closer to Sherry's oil-slick buttocks and positioned my cock. "I'm going to slide into your pussy, " I told her. "I'm not going to do anything else yet." She didn't say a word, but arched her back slightly to thrust her wet groin further back towards me. I could see her pussy lips full with arousal. I slid my cock deeply into the hot moist cave, not daring to pump in and out for fear I would lose my own control. Steadily, my thumb worked in and out of Sherry's anus. The hunger to sheathe my cock in that ring of tight flesh grew stronger.
I poured another stream of scented oil into the valley between Sherry's ass-cheeks, letting it flow around my probing thumb and down to her pussy and my cock. I rubbed my index and middle fingers along the oily canyon, pressed them tightly together, slid my thumb out, and pushed my two fingers into her butt hole. Sherry moaned softly and I felt her muscles contract around my fingers. I waited a moment and then, rather than pumping them in and out, I began to slowly rotate my hand, back and forth, my two fingers together massaging the entrance to Sherry's back tunnel. The walls were slippery with oil. Slowly, very slowly I began to slide my cock in and out of her cunt, then matching the motion with my fingers. I was almost ready for the final step towards taking her anal virginity and, although I had not told her, mine own. Although I had watched absorbed on dozens of videos as pornstars fucked beautiful round asses, I had never had opportunity to taste these fruits before.
I slipped my two fingers out, made a triad with them and my ring finger and with hardly a break in the rhythm, I pushed the tips of my three fingers into Sherry's anus. She gasped sharply and I felt her muscles contract about my fingers. But she didn't ask me to stop. Leaving my fingers motionless, I lowered my hips a few inches so that my cock shaft pressed firmly against Sherry's clit, thoroughly wet with the oil and her own abundant juices. I rocked my cock in and out of her pussy steadily, my cock stroking along her clit with each thrust. Gradually her anus muscles relaxed so that I could again rotate my hand, preparing the opening for my cock. "Sherry," I whispered hoarsely, "can you reach under to play with your pussy?" She didn't answer, but I could see her push her right hand under herself and in a few seconds I could feel her fingers brush against my cock as she stroked her clit. Now was the time. I pulled my cock out of her pussy, slid it two inches upwards, removed my fingers from her anus, and slid my cockhead into the waiting tunnel. At the first sign of resistance from the encircling ring, I stopped moving but maintained a firm, gently pressure. Well lubricated, my cock slowly slipped in deeper. With nearly half my seven inches buried in Sherry's hot, slippery ass, I stopped. "Are you okay?" I asked her.
"Yes."
"What would you like me to do?"
"Fuck me," Sherry said. "Fuck me in my ass." I was sure then that Sherry, despite her initial worry, was doing fine. She knew how turned I got when she "talked dirty" to me during sex, something she usually did when especially aroused. I slowly pulled my cock back an inch and pushed it back in, Out again and in again, slowly thrusting deeper until about two-thirds of my oil-slickened shaft was being buried in Sherry's gorgeous butt. "Fuck me, fuck me," she continued to murmur. I could sense her fingers working rapidly at her pussy.
A fire raged within me, demanding to be released. "Should I cum in you? Should I cum in your ass?" I panted.
"Cum in my ass! Fucking fill up my ass with your cum!" Sherry said. I could no longer hold back and, with a final thrust that buried me even deeper in her back tunnel, I let myself go, shooting inside her. I felt as if a quart of cum must have poured out from me.
Spent, I pulled my cock, scarcely softened, out of Sherry's anus. As the hole contracted, gobs of thick cum slid out and ooze downwards to her pussy, flowing into the half-open cleft and on to her urgent fingers. A new hunger replaced the one just expended in her ass. I quickly bent down and pressed my face into her messy, wet crotch. I greedily licked at the warm, sticky flesh, my nose pressed into her cunt, and I pushed a thumb back into her hot, tight ass. My tongue raced over Sherry's swollen clit, sending her into spasms, moaning and thrashing uncontrollably. I lifted myself up and kneeled behind her, holding her body in my arms, my head resting on her back. This was our first anal experience, but I was certain it would not be the last.
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goodguyguitarist
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