Sex and Fun in San Francisco Ch. 03bystatestreet©
Chapter 3: Saturday Night
I was extremely excited! I knew from looking in Charlotte's bag of goodies from the drugstore as well as the twinkle in her eyes and the sultriness of her voice that we were in store for lots of anal fun. While Charlotte enjoys vaginal stimulation as much as any other highly sexed woman, she has a particular fondness for anything involving her thighs, especially her inner thighs, and her bountiful buttocks. She has had orgasms just from having her bottom lightly stroked!
Charlotte had said it would be about an hour before she emerged from the bath. Time passed very slowly. To make the most of it, I bought an adult film and watched it on the room's TV. The movie was actually better than I expected. The lead actress, a good-looking brunette in her 30's or maybe 40's, did not look to me to be acting at all. She seemed to genuinely enjoy all the sex acts she performed, whether giving a blowjob, straight fucking, being DP'ed, or engaging in a lesbian encounter. It helped that she appeared to be totally natural and that her use of makeup was sparse. I got so into the movie I stripped off my clothes and began to masturbate. I became very hard and was nearing the moment of ejaculation.
That's when Charlotte came into the sleeping quarters totally nude. She had shaved off her pubic hair and her slit was quite prominent. She saw me beating off and noticed what I was watching and asked if I was doing it because of her or that slut on the TV. I nodded my head "Yes" and let it go at that. Charlotte walked toward me in a sensuous way that made sure my eyes stayed locked on her hairless cunny. She asked if I wanted to help her "have fun" or if I preferred the movie. I turned off the TV.
Charlotte lay face down on the bed. She put a pillow under her crotch and asked me to massage her. I began with her feet. I worked the tops and bottoms of her feet, using a grip that was firm but wouldn't hurt her. She sighed in enjoyment. I then spent some time on each toe, ending by sucking each one into my mouth. Charlotte likes that a lot! After the feet were done, I began massaging her calves. I used long strokes, just the way she prefers. Then I spent a minute working the area behind her knees. Charlotte cooed with pleasure. She opened her legs wide so that I could have access to the insides of her thighs. I peeked toward the tops of her legs and noted her pussy was plump with excitement and it had begun leaking woman juice onto the pillow.
I spent considerable time rubbing and stroking her thighs. I ran my dry tongue over her flesh, feeling all the tiny bumps on the backs of her thighs and the hot silky softness of the inner areas. Charlotte was now leaking a goodly volume of pussy nectar onto the pillow. The smell of her arousal was powerful and I was very tempted to go down on her and then fuck her until we both came. But, much as I wanted to, I didn't.
I got on my knees between her legs and began working on her buttocks. She was very relaxed as I kneaded those fleshy globes. It was a lot of fun for both of us. After about 15 minutes I sensed she was ready for the main event. I got off the bed and grabbed the bottle of lubricant and a surgical glove from the drugstore bag. I snapped on the glove and opened the lube. Charlotte turned her head to watch. I soon got back in position between her legs. I squeezed out a large dollop of lube onto my gloved forefinger and asked her if she was ready.
"Yes, do my asshole, please do my asshole!" she cried.
I spread the lube over the length of my finger and bent down to get closer to her asshole. I just barely touched her brown hole with my finger. Charlotte's reaction was more than I anticipated; she actually came! Woman slime was almost gushing from her vagina onto the pillow beneath her hips. I touched her anus again and began pushing my finger in. I very slowly pushed in and pulled out, then pushed in just a bit more. After several cycles, my forefinger was in past the second knuckle. Charlotte was moving her hips in all directions trying to get as much stimulation as she could. I pulled out my finger and reapplied the lubricant, only now to the fore and middle fingers. I repeated my actions except with two fingers instead of one. Charlotte was alternately hissing and sighing. She was enjoying this quite a lot. Before long a third finger had entered her heinie and I began a corkscrewing motion that got Charlotte's attention.
"Do that! It feels so good! Don't stop!"
Well, I figured if three fingers felt that good, then four would feel even better! I pulled out of her butt, much to Charlotte's protestations. I gave her slap on the rear and told her to quiet down and that I had some surprises in store for her. Charlotte stopped complaining and impatiently waited for what was to come. I lubed all the fingers except for my thumb. The forefinger went in first, quickly followed by the middle, ring and pinky fingers. It was a very tight fit, but Charlotte was up to the task and soon her anal area had stretched enough to make my fingers feel comfortable inside her. She was hyper-stimulated and I'm certain she came at least a couple of times. I rotated the mass of fingers in her butt and she responded by violently thrusting her hips up and down. With each upward thrust my fingers were buried as far as they could go into her bowels, while each downward thrust was almost far enough for my fingers to come out. She did this at least a dozen times before I purposely allowed my fingers to be freed of her hot butt. Once again she complained and again I gave her a swat on the ass to quiet her down.
It was the moment of truth. All five fingers were thickly coated with lubricant. I told Charlotte her big surprise was in store. She mewled in anticipation. I did the best I could to form my hand into a wedge shape, with my thumb tucked into the palm. I started pushing in. It was not an easy journey so I took things very slow. After several false starts four fingers were in up to the second knuckle and the tip of my thumb was touching Charlotte's anus. I asked if she wanted me to continue. Charlotte slightly lifted her hips in answer. I squirted some more lube onto her asshole and my fingers and started pushing in again, very, very slowly. My thumb entered her hole. Soon it was in past the first knuckle and before long I had reached the widest part of my hand. I took a deep breath and made one final push. My hand was now completely in Charlotte's ass, buried up to the wrist. I asked Charlotte how she liked it.
She was almost breathless in her reply, "It feels like a really hard gigantic cock. I feel very full, but in a nice way. Move around a little and I'll tell you what it's like."
I wiggled my fingers a bit and rotated my wrist. The way she described the sensations left no doubt she was enjoying this to the utmost! My hand was in there maybe 2 or 3 minutes before I told her I was going to pull out. She asked if I really had to and I answered yes. I slowly began withdrawing my hand. The wide part was a bit of an effort to pull out, but once it was free, the rest of my hand slid out very easily. I took a look at Charlotte's asshole. It was very wide and I could actually see some of the internal structure. I pulled off the glove and fell onto the bed. I was covered in sweat. Charlotte rolled over and told me that was the best gift I'd ever given her.
She was still horny and asked if I wanted to fuck. I looked at her and said "Sure", or some similar clever remark. She got a condom from the bag and rolled it onto my throbbing cock. She positioned herself in a reverse cowboy and let my prick slide into her loosened asshole. She controlled all the motion and was soon moving up and down with wild abandon. By the time I was ready to come, her asshole had regained some of its tightness. I let loose a large quantity of sperm into the condom. After a few seconds, Charlotte got off my cock and rolled off the used rubber. There was quite a bit of cum filling the reservoir. She tipped the rubber upside down and let my still-warm spunk dribble onto my chest. She tossed the empty rubber to the side and proceeded to lick the cooling cum off my torso. As she finished, she moved up to my face and kissed me on the lips. Charlotte's tongue wormed its way into my mouth, transferring some of the sperm back to me. I don't especially like the taste of cum, but sometimes it pays to let Charlotte do what she wants.
She thanked me for the best sex she'd ever had and said she'd have a surprise for me tomorrow. She only hoped it would be as nice as mine was for her. I was sure it would be!