Trolling Craigslist, Part Three

I could not tear my eyes away from it. I knew what it was, but I was having a hard time processing it. Tammy was amazing and I could not remember the last time I had enjoyed a date so much, but being confronted with who she really was had thrown me for a loop.

“Ed?” Tammy asked.

I looked up at her and her cheeks were flushed red. “I’m sorry,” I stammered. “I didn’t mean to stare.”

“It’s okay,” she said. She bit her bottom lip and knelt down in front of me. “What do you think?”

“I’m not sure honestly. I’ve never been…” My words trailed off. I wasn’t sure what the right words were.

“With a girl who has a dick?” Tammy finished for me.  I nodded dumbly. “Its okay. If you want to leave. I would understand, and if you want to stay we can continue where we left off.”

I was a little unsure about all of it, but I knew I didn’t want to leave. “I want to stay,” I said, “but I am not sure what to do.”

She smiled and put her hands on my knees. “Its okay. I’m just like any other girl, but some of the options are different. I’m not going to force my cock on you,” she said, “but I’m not going to hide it away either. How much you want to play is up to you.”

“Sounds reasonable,” I said after wetting my lips. “Why don’t you take off those panties. And let me have a look at you.”

Tammy looked at me and cocked an eyebrow. “Are you sure?”

“This is all new to me and I would rather wade right in than tiptoe around it,” I said.

She looked into my eyes and must have liked what she saw, because she whispered, “Okay, Ed, if that is what you want.” Tammy stood up and took a step back. I could see her in all of her glory, but I kept my eyes locked on hers. She put her fingers into the waistband of her panties and pushed them down until they fell to her ankles. Tammy stood before me, naked except for the stockings and garter belt, and she was magnificent. She held herself tall and proud, and waited for my reaction.

I looked at her semi-stiff member and was a little pleased to see that even hard it was unlikely to be as long as my own, but it would be close when compared side by side. She was completely shaven, circumsized, and not quite as thick as me, but by all standards it was a nice cock. I was not normally in the habit of comparing myself with others, but for some reason i found it oddly important this time. Perhaps it was because being bigger made me feel more manly, but it really didn’t matter, at least not to me in that moment.

“Well, what do you think?” Tammy asked.

In response, I stood, stepped close to her and grabbed hold of her dick. “It’s very nice,” I said before kissing her. Tammy moaned into my mouth and within seconds her cock was every bit as hard as my own.

Tammy pulled away and pushed me onto the couch. “I believe there was a little something going on before we took that little break,” she said before she crawled onto the couch beside me. She was on all fours and moved into position so that she could once more take my cock into her mouth. She was slow and deliberate in her motions as she teased me to the point of complete exstacey.

I was lost in the pleasures of Tammy’s mouth when I felt something touch my arm. I knew exactly what it was. I grabbed onto her cock and stroked it from base to tip, just the way i like it, and when I foundit precum collecting on the tip I ran my thumb across it, smearing it all over her tip. She moaned and ran her hand up and down my thighs before cupping my balls. I stroked her cock faster until she pulled up from my dick and said, “Stop, Ed. I don’t want to cum yet.” I stopped stroking and she went back to sucking my cock, but I was not done playing with her just yet.

I leaned over so that I had more reach before I ran my hand up her thigh. I carressed her balls briefly before moving further up and running my fingertip against her ass. She arched her back in response so I continued for a moment or two longer before I pushed the tip of my finger inside.

“Damnit, Ed,” Tammy said, “I am trying to focus here.”

“Good luck with that.” I laughed and pushed my finger a little further in.

Tammy sat up and slid all the way onto my finger. She moaned and rocked her hips back and forth as I finger fucked her ass. Her tits bounced with the rhythm of her motion, but her cock swayed like a cobra and I found myself mesmerized by it. I leaned over and licked the underside of the tip and Tammy moaned. I hesitated for only a moment. I had come this far. Why should I hold back now?

I opened my mouth and held Tammy’s cock between my lips. I tried to remember all of the things I liked when receiving a blowjob and proceeded to use those very techniques on her. I licked and sucked on her dick the best I could, and though I am sure my attempts were awkward, Tammy seemed to be enjoying herself.

“God damn,” she mumbled before extracting herself from my mouth and finger. “Are you sure you’ve never done that before?” she asked.

“This has definitely been a first for me, ” I said.

“I had planned on going at this a little different, but I need more than just your finger right now,” she said.

“What the lady wants, the lady gets,” I said as I sat back on the couch. I took her hand and pulled her a over so that she stood between my legs. I turned her around, grabbed her by by the hips, and pulled her down. My cock was still slippery with Tammy’s saliva, so when i pressed the tip against her rosebud it slipped right inside.


Tammy leaned back against my chest and I started fucking her with long slow strokes. Her ass was tight around me, but my cock slid in and out of her with ease. I wrapped my arms around her and grabbed her tits. I pinched her nipples hard and she cried out. “Fuck me harder. Fill me with your cum.”

I had been on edge since the restaurant, so I did not need much encouragement. I fucked her harder and faster until I could no longer contain it. I cried out as pumped load after load of cum deep inside her ass. Tammy collapsed against me and road out my final thrusts.

Once I finished , she stood up and turned around. She bent over and kissed me. She grabbed my cock and stroked me slowly. Tammy broke our kiss and asked, “Have you ever been fucked in the ass?”

“Once,” I said, “with a strap on, but it was nowhere near as big as you are.”

“Strap ons are nice, but they are no substitute for the real thing,” she said with a smile. “Would you like to give it a try? I’ll be very gentle.”

“Yeah, why not?”

“Mmmm good,” Tammy said as she stood up. “Wait right here,” she said before turning and walking away.

“I don’t think I could leave even if I wanted to,” I called out to her as she turned down a hall.

A few seconds later she returned carrying a bottle of lubricant. “I suspect you’ll be a bit tighter than me,” she said. She knelt between my legs and set the bottle on the floor. She took my cock back into her mouth and sucked me clean. I could hardly believe that she was able to get me hard again so soon after one of the most intense orgasms I had ever experienced. Once she was satisfied, Tammy spread my legs apart and told me to raise them up and keep them there. I did as she asked, hooking my hands behind me knees so the I could keep my legs where she wanted them.

Tammy poured some of the lubricant on my cock and used one hand to stroke me. Each time her hand passed over the tip I twitched and nearly dropped my legs, but I managed to keep it together. While she distracted me with her hand she moved into position and rammed her tongue into my ass. I moaned and held my legs a little higher, wanting more. She fucked me with her tongue for a couple of minutes before replacing it with a pair of well lubricated fingers. She took her time and slowly stretched me out. Once she thought I was ready, she stood up and said, “Look at me, Ed.” I pried my eyes open and looked her in the eyes. “Are you sure you want this, because you don’t have to you know?”

I was so turned on in that moment that I would have agreed to just about anything. “Yes, I’m sure,” I managed to say between breaths.

“Good.” She squirted some of the lube into her hand and worked it over the length of her dick. “You tell me if you need to stop.”

I nodded and tried to relax. I knew it was going to hurt at first, but clenching up would only make it worse.

Tammy guided the head of her cock to my anus and slowly pushed forward. I gasped as the head entered and moaned as she slid the rest of her length into me. It did not hurt as much as I remembered, but that might have been because I was nearly delerious with ecstacy at that point in the evening. She grabbed my cock and stroked me in time with her thrusts as she fucked my ass.

I don’t know when she started fucking me as hard as she could, but by the time she called out that she was coming I was lost to the universe. My whole existence was alight with pleasure and when I felt her cum inside my ass my world exploded. My back arched uncontrollably and I came for the second time that night. Thick streams of my cum splashed against my chest as I cried out.
When I finally came down from the orgasmic high I found Tammy lying against my chest and her cock still inside me. I ran my fingers through her hair and she made little pleased noises.

“Tammy,” I said.


“I don’t want to be presumptive, but what do say about you and I heading to bed and cleaning up in the morning?”

She lifted her head and smiled at me. “I think that would be a great idea.”

We got up from the couch and she lead me to her room. We got into bed and she snuggled up to me, her back to my chest. “I am so glad I answered that add,” I whispered and kissed her neck.

“Me too.”

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