Working Extra 04

I was lying on Shelly's large couch in her living room and she was watching me. She had insisted that I wear the undies she had bought me, and it was like she couldn't get enough of watching and touching me when I was dressed up like this. I didn't mind though, as we were having the best sex I had ever had. She was both gentle and strong at the same time, and like magic, she could read my mind, knowing what I wanted. And each time we met, she taught me new things.

"Show me your sweet butt, baby," she said. "Kneel on the couch and stick it out for me."

I quickly did as she asked. I got up on my knees and leaned against the back of the couch. With my knees a bit apart, I stuck my butt out for her and looked over my shoulder at her, smiling. I was wearing that open crotch thong, and in this position, it wasn't hiding anything.

"Like this?" I wiggled my hips a little to tease her.

"That's perfect." She walked up to me and placed her hands on my buttocks.

"I just love your ass, babe. It's so warm and soft." She continued while kneeling behind me.

She started kneading my buttocks and thighs, using her thumbs to make the outer lips gently move and rub against each other. It didn't take long before I could feel my juices lubricating my vagina.

I reached for a pillow and hugged it while still leaning against the back of the couch, closing my eyes and quietly moaning as she was teasing me. I loved how she used her thumbs, how she made me so horny without touching my sex. "I'm even speaking like her," I thought, smiling to myself.

She kept massaging me with her hands, and then I felt her warm breath and then her lips on one of the buttocks. At first, she only used her lips but soon she used her tongue as well. The sensation made me shiver and I could feel goosebumps on my arms and my buttocks.

"My baby loves what I'm doin' to her?" She asked.

"Yes. Please eat me, I want to feel your tongue."

"Good girl! You are learning to tell what you want." She gave my buttock another kiss.

Then she pulled down my thong and I did my best to help her take it off. Again, her tongue returned to my behind. This time the tip followed the cleft between my buttocks, slowly working its way down. She used her hands to pull the cheeks apart and suddenly, I felt the tip brushing over my tight rosebud. For a moment I tensed. "Oh gosh! She's gonna use her tongue there!" It felt both exciting and a little scary at the same time, but she was so gentle that I quickly relaxed again.

"Have you ever had anal sex, love?" She asked.

"Me and my ex tried it a few times, but It didn't work."

"I can imagine. Most men have no idea how to do it. Trust me, I know all about anal." She laughed. "If you do it right, it can be wild. Wanna try?"

I hesitated. My ex had kept insisting on trying anal and it was one of the main reasons we broke up. But I trusted Shelly, and her hands and tongue had felt so good that by now I was willing to give it a shot.

"Ok, let's try," I whispered.

She kissed my buttocks and then placed her tongue right on the centre of my rosebud again. She flicked her tongue against it, kissed and licked. I felt how her saliva made me wet and slippery, not only where she was using her tongue, but also further down.

"I'll use plenty of lube, sweetie."

She reached for something under the couch and then I could hear a cap pop open. A second later I felt something running down the cleft. She used her free hand to massage me. She placed the tip of her finger right at the centre of the bud and slowly started to press and wiggle.

"Now, relax babe," she whispered.

While one of her hands was working on my rear, her other hand moved down and in between my thighs. When the thumb sunk in between the folds and into my vagina I moaned loudly.

"Oh yeah!"

To my surprise, I didn't just have her thumb inside me, she had also worked one finger into my butt without me noticing.

"Relax honey, an' let your body get used to it."

I did my best. Slowly she began to move the finger inside my butt. At first, she just rotated it a little and then she started to move it in and out again. It was a strange feeling, and not unpleasant at all. In fact, it felt very erotic having her fill both my holes like this.

"You're ok, baby?" she asked.

"Oh, God, yes."

She leaned forward and placed a kiss on my buttock. She fingered me for a little while before she pulled out.

"I think you're ready for somethin' bigger."

I waited, excited about what she had in store for me, and at the same time dreading what that bigger thing would feel like. I heard her open the bottle with lubricant again and gasped when she applied a little on my rosebud.

"Here we go baby, relax."

I felt something cold poking at my rear, and I tried to relax. I could feel that it was something larger than her finger and it stretched me and suddenly it popped inside. I was so slippery that whatever it was, it slid in almost without friction.

"You're doin' fine baby, takin' that plug all the way in like that. Now, let's see how you're likin' these vibes."

Before I could ask what she was talking about, she switched on the vibrator.

"Ahhhh!" I squirmed a little when I felt the slow but powerful vibrations from the plug, spreading through my pelvis and reaching my vagina.

"It's too much?"

I shook my head "No, not at all."

It was the weirdest sensation I had ever felt, but it was good, really good. One of her hands returned to my pussy and her other played with the controls to the vibrator, and she quickly brought me to a shivering climax. I was hugging the pillow tight and moaning into it as I rode the waves of the orgasm.

Shelly turned down the vibrator but left it slowly humming and still in place. She gently stroked the sweaty skin on my back as I was calming down.

"I think baby had a good time," she chuckled.

"Oh yes. You were right, it was wild."

I was still hugging the pillow but was looking back over my shoulder at her. I could feel the soft vibrations and the effect they had on me. I'd already had an orgasm, but I wanted more.

"Please, fuck me. Fuck my ass."

"You want this she-cock in your ass, baby?"

She smiled as she showed me her stiff cock, slowly tugging on it. I could already see that there was a glimmering drop of pre-cum at the top.

"Yes. I want your cock in my ass." To show what I meant, I placed my palms on my buttocks to spread the cheeks for her.

"You are such a little slut," she laughed and reached for the plug in my butt. "And tonite love, I'm gonna make you my little anal slut."

She turned the vibrator off and gently removed it, and to my surprise it gave a sense of emptiness. I watched her as she poured some lubricant onto the shaft of her cock and then she got into the position right behind me. With my hands I again spread my cheeks for her as she let the tip of her cock poke on my bud. I took a deep breath and tried to relax.

Slowly the tip pushed inside and again I could feel my sphincter being stretched. She slowly increased the pressure and for a moment I could feel a little pain. Then my muscles relaxed, and she was inside.

The sensation of being filled up by her was amazing. If the plug had felt good, this was something extra. It felt exciting, forbidden, and having her cock inside my anus gave me a strange but exciting feeling.

"You're ok, baby?" She whispered in my ear.

I nodded and she kissed the side of my neck. I wiggled my hips a little to get a better feel for her and to make sure she was fully inside. I felt just as excited as I had been just minutes ago when the vibrating plug and her fingers had driven me to my orgasm. I hugged the pillow and mumbled.

"I'm ready. Fuck me."

She gave me another kiss and slowly started to pull out, and then in again. I gasped for breath fearing she would slip out and then sighed when she slowly but steady pushed in again.

"You're doing fine, honey," she whispered.

Then she started to move a little bit faster, and the sensation was incredible. It felt like she wasn't just fucking my rear, I could feel my pussy moving as well, moving and rubbing my clitoris. It was just amazing.

Being caught between her and the pillow increased the feeling of helplessness, being at her mercy, a sensation I had never felt before, but it excited me. I moved a hand down between my thighs and my fingers found my soaking wet pussy.

"Oh, gawd! You're the tightest ass I have fucked in ages. I'm gonna fill you with my cum!"

I could feel her intensity increasing as she neared her climax and I fingered myself almost desperately, trying to reach another orgasm.

"YEEESSS!"

With a final thrust, she buried herself as deep as she could, and I felt her body spasm as she came inside me. That was enough to push me over the top and my second orgasm exploded. It was intense. The waves made me shiver and shake, and I screamed into the pillow. If it hadn't been for her weight on top of me, and the fact that I was still hooked by her cock inside me, I would have slid down onto the floor.

I don't know for how long we lay there, me curled up on the couch, still hugging the pillow, and her resting on top of me.

"That was intense." she whispered.

"Mmm... it was. I couldn't imagine it could be like this. Thank you so much." I turned my head to kiss her.

"See? It's awesome when you do it with someone who knows what she's doing, and us she-cocks are the experts." We laughed and she hugged me tight.

"And you are the cutest li'l anal slut I've ever fucked," she whispered.

We hugged for a while before she looked at me and spoke again. "You're so cute and look so hot in those fishnets, if only I could keep you like this forever."

"You're so darn cute, let me take a picture," she continued.

"Like this? Seriously? Why?" I looked up at her.

"So that I can watch you whenever I miss you. I won't show anyone."

I watched her for a couple of seconds. It felt crazy, but I was in a bit of a daze. "You promise?"

"Of course, love," she leaned closer and gave me a soft kiss. "Just for me."

"Ok, let's do it."

She hurried off to fetch her phone and then she made me pose on the couch for her. At first, I felt a bit tense and unsure, but soon I relaxed. We'd done some modelling back in class and it quickly came back to me.

And after all, it was just for her.

*

Later, she fucked me again, slowly and gently. That night I learned that I enjoyed not only the orgasm I got while having her dick up my rear, but I also realized that I enjoyed the sensation of being pinned down under her, helpless and being her sex toy.

It made me think of that single glove that Angela had shown me when we were in the shop. I asked Shelly if she had ever played with one, but she hadn't. She wasn't into BDSM, she said. For some reason I wasn't expecting that and deep down I felt a little disappointed.