It was a rare Friday morning for me. I had the house all to myself. Jake was off on a bike ride, Mom was out doing whatever she did with her days and I was naked (because I like being nude) busy packing for our weekend tip, the first we'd been able to go on in nine months... to a nudist resort.
I was nervous about it. My naked time around other people was still pretty limited. I'd been skinny dipping in some of the lakes and streams with Jake and his friend Maddie when I'd tagged along on their bike rides. We'd been nude at Steph and Maddies quite a few times; I'd even been daring and drove home naked the last few times.
That was a huge turn on.
I was headed for the kitchen when the doorbell rang. While grabbing my door answering robe, I caught my reflection in the mirror and I liked what I saw.
Bicycle rides with Jake combined with morning and evening yoga with Mom, had done wonders for my body. I was never going to be in danger of blowing away in a strong wind, but I'd lost a few dress sizes, my tummy was far less doughy and my butt had slimmed and tightened too.
Even though being as enthralled as I was with my progress, I still donned the robe and answered the door.
The UPS drivers face flashed a slightly disappointed look when I answered the door. Being the package didn't actually need a signature and could have been left on the porch, it didn't take a genius to figure out why.
"Sorry, Irina's out today, so you're stuck with me," I told him.
"No, she's just such a nice lady, I enjoy seeing her," he replied. "Not that you're not a nice lady."
Even at seventy two years old, my mother had an incredible body and liked flaunting it. As she spent all of her time at home nude, she saw no reason to cover up when she was doing trivial things like answering the door for strangers, the pool guy or anyone working on the house.
I'm not sure what came over me at that moment...
"Yes I'm sure you've seen a lot of her," I smiled. "I hate to disappoint, why don't we try this again?"
I shut the door, took off my robe, held my breath and waited.
The doorbell rang.
I answered the door.
"Hello, I see you have something for me," I said, actually feeling more naked than I did the Saturday I surprised Jake in my office.
My pussy started getting moist as his eyes travelled from my face to my boobs then over my blonde muff, right down to my toes.
"Yes ma'am," he said to my boobs as he handed me the package.
"Do I need to sign?"
"No ma'am, I just wanted to make sure you got it."
"How very kind of you," I gushed and so did my pussy.
We stood at the doorway awkwardly for a few seconds while I let his eyes roam up and down my body. The bulge in his shorts told me he liked what he saw.
"Umm, I'm not sure what Irina does for you at this point, but this is as far as things go with me," I told him, breaking the silence.
"No ma'am nothing like that," he stammered. "I..just..you're really beautiful."
He made my day!
We said our goodbyes and I stayed in the doorway until he got in his truck and drove off.
I was dripping. I briefly considered fingering and getting myself off right there on my porch. While I desperately needed some relief, being caught naked outside was one thing, getting caught naked and masturbating was one of those things people went to jail for.
Reluctantly I went inside and closed the door.
With the door against my back, I squatted, spread my legs and ran my fingers over my wet slit. I was very wet, my fingers slipped effortlessly over my lips, my clit and inside of me. I smeared my juices over my pussy, even letting them drift a bit to tease my ass.
Two fingers from my right hand gliding in and out of my pussy, while two fingers of my left hand ground my clit felt great, but I just couldn't push it over the edge.
Forcing myself to get up, I headed towards my bedroom and dug into my suitcase. A moan escaped my lips as my hand found the soft velvet bag. My pussy quivered as I dropped the jeweled, stainless steel plug into my hand. Another quick search in my bag for a bottle of lube and I was ready to go or cum, as it were.
It started out as a joke. The first time the subject of anal sex came up, or rather I asked Jake to, as they say, do me in the butthole, he joked that he'd like to save that for our wedding night.
In his defense, the situation in which I brought it up would have been inconvenient. We'd snuck away for an in the bushes quickie at a friends party. I was bent at the waist and Jake had his hands on his hip as he was pounding me from behind. My boobs were out of my dress, bouncing with every thrust. The situation had me just as turned on as the actual sex....I was in Hannah porn mode.
"Fuck my ass," I pleaded when he ran his fingers over my butthole.
As I said, he was right at that moment. We didn't have any lube with us and clean up would have been problematic.
I did like hearing 'not until our wedding night' much better than an outright 'No' and for the record, I rubbed my clit until I came on his cock. Then turned around, dropped to my knees, took his Hannah gooey cock in my mouth until he filled it with cum, tucked my boobs back in my dress and we got back to the party in time for dessert.
The wedding night comment became a running joke between us. While I liked it that he was thinking along the lines of our relationship becoming permanent, I really wanted to experience anal sex and so far....How can I put this in a lady like fashion?... My butt remained un-fucked.
I promise, I'll get back to the main story in a minute, just one more loose end to tie up.
In the course of my sexual research if I was to put it in academic terms, or in lay terms, watching porn and masturbating, I got interested in butt plugs. The thought of wearing one was daring and exciting. I liked Jakes and on occasion my fingers there and don't get me started about when he licks me...
My interest soon turned into an obsession. I wanted to know what a butt plug felt like inside of me, while Jakes cock slid in and out of my pussy. I wanted to have my special dirty secret while I wore one while I was out shopping. On the practical side, I wanted to use it to get used to things going in back there for the night when I finally talked Jake into taking my butt-ginity.
When the obsession finally got to great, I got on Amazon and ordered a matching pair. Two days later, the package arrived on an evening when Jake was at Maddies playing with bicycles and Mom was out doing whatever Irinas do when they're out in the wild.
Porn knowledge over road common sense when I lubed up the tapered ball of my purple jeweled beauty and slid into my butthole in one motion, just like I'd seen in the movies.
FUCK MY ASS! That hurt.
If I'd been standing, my knees would have buckled. Thankfully I was on my side. A part of me wanted to pull it out, but common sense finally kicked in when that little voice in my head told me it would hurt as much coming out as it did going in. I wiped the tear that formed in the corner of my eye, did a few deep breaths and started rubbing my pussy.
After a few minutes, the pain started easing. In fact, that feeling of fullness was downright pleasant. The more I vigorously I rubbed myself, the more it moved inside of me, making the inside of my butt and my pussy tingle in delightful ways.
Once I got going, it didn't take me long to climax the first time, or the second or the third for that matter.
The fourth time, hung there. I wanted to cum, I was close to cumming, I just couldn't get over that hump.
Hump? I thought. I liked humping things...and people (well, Jake). Grinding my wet pussy against his pubic bone while his rock hard cock was deep inside me, was a form of humping. Pressing myself against his leg while we kissed was kind of like humping. Rubbing my pussy on his thigh, out by the pool, while it was covered in suntan oil and climaxing like a crazy woman....was definitely humping.
Unfortunately Jakes leg was probably straddling a bicycle at that moment, when I wanted mine straddling his, so he was no help.
Looking around the room, my eyes fell on a cylindrical bolster pillow that I'd bought years before and pretty much hated once I got it home.
I sent up an apology to the pillow Gods as I reached for it.
Throwing my leg over and dropping down on it...I was in heaven. It was perfect, just the right height and a wonderful firmness. Rocking my hips back and forth, my clit dragging across the soft material while the plug moved in my butt had me well into my fourth climax in record time. I loved the way my butthole clenched the plug and sent vibrations through my pussy. With a little help from my mouth, biting and licking my own nipples, climaxes five and six occurred one right after another, which left me spent.
