Adventure with Anna Pt. 01

I woke up from my nap feeling horny. She had recently made it a rule that I sleep naked, and I would consistently wake up with a raging hard-on. It was Saturday, and I had nowhere to be so I gently rubbed against the soft blanket, lingering in bed and remembering that Anna would be over in the next hour or so.

Drifting back to some half-sleep, I thought of the things Anna would do to me if she found me lying in bed touching myself. How proud she'd be that I was good and followed her instructions to always sleep naked. How she had offered to take me for a drive anytime I decided I had the courage to ride in the car naked with her... I had always imagined that the drive would happen after dark. But I woke up again and had decided that I'd ask her to take me today.

The soft blanket rubbed against me, my cock dripping precum from the excitement of the idea. My heart pounded in my ears as I heard the front door open, and then the bedroom door...

Anna saw my smile immediately, "what have you been up to?"

"Napping" I replied.

"Have you been good for me? I can see you have." as she gestured toward the tent under the fuzzy blanket. She reached under the blanket, grabbing me gently, but authoritatively at the base of my bare cock. She swung it side to side slowly, "you've been very good." as the head of my cock rubbed gently across the fuzzy blanket. She knew how sensitive this made me.

"How would you like me to reward you for being so good?"

I knew she'd do anything I asked, she'd proven this more than a few times. "Can we go for that drive you've been talking about?" My heart in my throat as I asked...

Her smile broadened, a flash of evil in her eyes. "Where should I take you?"

"Anywhere you want. I trust you."

"There's a place I know of, where I can take you into the woods. I think it'll be private, but it's Saturday so who knows?"

The place she told me about was where she had gone one day. Years before, Anna had done a few porn videos.

She described to me how, in one video, she left her clothes at home and a couple of guys walked her out to the car naked. They drove her out to a somewhat private spot in the woods where she put on a show for them, she told me about how she came over and over, touching herself for the camera and loving the attention and exposure. She saw how this story turned me on as she told it.

She took me by the hand and walked me to the kitchen table. "Touch yourself" she ordered. She watched as I rubbed my shaft... "on the tip" she commanded. Anna knew what felt best.

"Sweetie, I'll come too quick" The excitement was too much, and I could feel my orgasm quickly building.

"Come for me now." She loved the control she had over me, and held her hand out as I exploded on her. She quickly grabbed my cock from me and polished the tip as my orgasm faded. Using my cum as lube, she held the base of my shaft tight and rubbed my head quickly, gently, making me so sensitive after such an intense orgasm. She knew how I'd often ask for her not to stop, even after I cum, and how I'd scream and beg for her to stop as she'd polish the cum on my apple furiously, oftentimes using our safe word after only a few seconds of post orgasm torture.

Anna eased off this time, though. "Ready to go?" Horny quickly turned to shy, as I was handed my soft blanket. "You can take your blanket with you, so the neighbors don't have to look at your bare ass!"

I covered myself up as best I could, and she took my hand and walked me to the car. It didn't seem like such a good idea anymore in my post-orgasm clarity... but I felt brave as she asked "Do you trust me?"

"Yes". I sat down in the passenger seat of her older Mazda 6, covering myself with the fuzzy blanket.

"Put your seatbelt on, here give that to me." as she took my blanket and tossed it in the back seat. "You'll just wear the seatbelt" as she rolled the windows down. What had I gotten myself in to?

As we pulled out of the neighborhood, Anna reached over and gently held my softened cock, squeezing softly as she drove us to a nearby highway on-ramp. "Where should I take you?"

"Aren't we going to the woods, like you said?"

"I have another idea... mainly because I realize that we left without you wearing any shoes... and I wouldn't be taking good care of you if I made you do the hike without shoes on. My job is to take GOOD care of you today."

"I got a notification on my phone that a package has been delivered, and I don't want to leave it on the doorstep for long. You know how busy my neighborhood is."

Anna lived on a busy corner just south of town, and regularly had packages stolen from the porch. "We'll stop by there first." Fuck me, we're running errands now with me naked riding shotgun...

The gentle squeezing had turned to slow tugging as my cock began to fill back up. "Does it feel good? The sun and wind on your skin? I can tell he likes it!" She gave my hardening cock a gentle shake.

I stiffened even more as my heart suddenly leapt to the top of my chest... as we pulled around the corner and I could see Anna's roommate's car in the driveway.

"Stay here while I go grab the package." She left me in the car and trotted up to the porch, and into the front door. A moment later, she was back at the car grinning. "My package arrived. Want to come in and see what it is?"

I stammered...

"Don't worry. Jenny isn't here. She must be out walking the dog, because he's not here either. Come inside. You can wear your blanket if you want."

I grabbed the blanket and wrapped myself as best I could to protect me from the neighborhood's view... so many people were out on a Saturday afternoon... I walked quickly through the open front door. "Give me that" Anna took my blanket as I entered the house, "go lay down over there, on the rug".

Following her command, I laid myself down on the plush rug, just inside the front door as she closed, bud did not lock, the front door. Anna never locked the door, and what was usually just an annoying oversight now had me concerned. "What if Jenny comes home?"

"She probably won't, and if she does... well it'll be fine." I could feel the soft rug and cold air conditioning on my bare skin, and felt quite bare thinking of what might be coming next. "Oh, goody!" she exclaimed as she tore the box open and pulled out a small bottle. "Shut your eyes, I want to surprise you!"

Obedient, I waited for what seemed forever until Anna laid down beside me on the floor, I could feel her jeans rubbing against my thigh, her blouse on my shoulder, her boots poking at my bare feet. She knew how much it turned me on for her to have me naked, her completely clothed and in control. It turned her on too. "Give me your hand" she ordered, directing my hand into the front of her tight jeans. "Feel how wet you make me?" I eagerly pushed my finger, then two into her sopping wet pussy, making sure to rub right over her clit and making her body quiver. She pulled my hand back out, directing it to my mouth. "Lick my juices off of your fingers." Obedient as always, my eyes were still shut and I suddenly felt a cool drip, then another, right on the tip of my upright cock.

"I got some new lube for us to play with, love." She traced her finger over the head, then the shaft, then wrapped her hand around me and started pumping my slippery cock expertly, squeezing the tip and pushing me downward, both slippery hands taking complete control over me. She knew the power she had over me, naked on her floor, hornier than I had woken up that morning.

She knew exactly what to do with that power when she told me to open my eyes. Continuing to gently stroke me, she held up a small, black butt plug and asked "should we try the other toy that arrived today? I got it for you."

"Maybe" I said, shy all over again. We had played around a little back there over the last few months, but I had hardly had a fingertip in me. The small plug looked quite large now.

"We don't need to do anything you don't want to do." She assured me. But I did want it, so horny being so far from home naked, completely in Anna's care had me longing to have her inside me.

"I want to". "What do you want? Tell me."

She beamed as I told her "I want you to fuck my ass with the butt plug. Please be gentle."

"Oh love, I'll be so gentle!" She wrapped her thighs around me, I could feel her rough jeans rubbing on my rock hard cock as she gave me a slow, enthusiastic hug. "I'm so proud of you!"

She pushed me over to lay on my side, and I could feel the lube drip from her little finger onto my asshole. She rubbed the lube in and around as she continued stroking my cock, gently fingering my ass and helping me feel relaxed.

"You're so tight." she cooed as she pressed her finger in farther.

Rolling me on my back, she pushed her finger in farther still, and pushed my legs up with her shoulders as she continued to milk on my helpless cock.

I felt her pull her finger out and, not a moment later, felt the cool hard tip of the butt plug press into the hole where her finger had been. In a little, out a little, gentle and slow, I felt Anna slowly open me up while eagerly pulling on my dick. I moaned louder and louder as the butt plug pushed all of the way in, feeling my asshole stretch and then swallow the bulb at the base of the plug.

"You're so good for me!" I felt proud and full as she dripped some fresh lube on my already dripping cock and descended on it with both hands, tugging the shaft greedily and polishing gently on the tip coaxing me closer and closer to my second orgasm of the day.

So full of the buttplug, now Anna squeezing the base of my cock making it feel like it will burst, she switched from stroking to polishing... polishing my apple to expertly push my orgasm back in. It was a few months ago when she discovered that she could bring me back from the edge by polishing the head of my cock with the palm of her hand. The sensations from her slippery hand on my most sensitive spot, overwhelmed the overwhelm of an orgasm and would keep me from cumming. Since then, she would play with me regularly, and push me closer and closer to the edge, pulling be back over and over with her now skilled palm.

That control, in the hands of skill that can do things to me that I can't do to myself. Anna giggled as I would moan my pleasure... "I'm coming!" as I could feel it taking over, "not yet" as she'd show me the control she had. Making me want it worse and worse, pushing me over the edge and pulling me back, she suddenly released her grip on the base of my cock and pulled the butt plug out, halfway, and pushed it back in authoritatively. She pumped the full length of my cock furiously with her other hand, as she pulled and pushed on the butt plug, a little further out than before, and again. I don't remember how many times, but screamed as I shot my load high into the air. Anna made sure to jerk me the hardest as I came, and I felt my cum hit me on my chest, legs, arms, face... she really made a mess with my load, and kept fucking my ass gently as the pleasure turned too much.

Anna collected some of the cum and lubed my cock with it to milk me nearly as furiously as she had been. So sensitive, my ass now open and accepting the butt plug again and again, I screamed as I tried not to utter our safe word... "octopus!"

"Are you sure you want me to stop?"

I was sure that it was the only thing that would stop her, and hoped it still would as she chuckled at my suffering. I waited a second and said it again... octopus! OCTOPUS!"

She pushed the butt plug back in and stopped stroking me, instantly releasing me from the torture... but keeping a grip on my cock. "We should set a timer next time. And I won't stop until the alarm goes off, come what may." We had read about this as a technique to really push post orgasm torture to the next level. The torture will stop, but not until the time has elapsed. The suggestion was to start at one minute, but based on my experience with Anna's expert hands and mouth, that would be FAR too long to endure! "We could start at 10 minutes..." Anna joked, I hoped she was joking.

"10 minutes of post orgasm, that would be fun" I felt full of my butt plug as she traced over the tip of my cock casually with the tip of her finger. I was still hard, Anna horny and enjoying how hard I remained after such a strong orgasm. "No... that would be too much. Maybe 10 seconds, I'd lose my mind!"

"Well, regardless, I've got the timer app on my phone and maybe next time we play with it... you know you want to!" The thought had me stirring again, "you're a mess! Go get in the shower and I'll bring you a towel"