Part 9
I turned my head and I could barely see Caitlin out of the corner of my eye. She took her right hand and put it under my hip and pulled it up slightly. I raised my hips just a bit so that most of my torso was still on the mattress but there was now a slight distance between my hips and the bed.
I felt the cold of the lube as she squirted some into the crack of my ass. I then felt her finger massage the lube around the outer opening of my anus and then she began to push a little. She worked her finger in a couple of times and then withdraw it.
I then heard the squirt of the lube one more time and I could see her struggling the dildo jutting out from her crotch. Then I feel her move forward on the bed and I feel the tip of her dildo press up against my anus.
“Relax” She said “It will make it easier.”
I took a deep breath and she pushed. I could feel the dildo enter my ass. It was bigger than her finger, but about the same size as the prostate massager I had used. It wasn’t comfortable, but it didn’t hurt either. Once she was all the way in she said “Down” as she pushed her hips against my butt. I lowered my hips back to the mattress.
Without moving her hips, she reached up for my arms. She grabbed my wrists in turn and pulled them so they were behind my lower back. She then placed her right hand over both of my wrists and shifted a good deal of her body weight on them so that they were effectively pinned. I might have been able to struggle against her and free them, but I didn’t try. She then placed her other hand at the back of my neck.
Then Caitlin began to move her hips. She didn’t take more than two strokes before she picked up a vigorous pace.
“Oh, god…” I trailed off.
“Feels good, doesn’t it?” She asked. “You’re doing really well for your first time.”
“Oh… Oh… Oh… ” was all I could manage with each thrust she made.
I could feel the bed rocking. It hadn’t rocked like that since TiffAny put the device on me. I then started to think about Tiffany and how she held my key. Then I pictured that it was her back there instead of Caitlin. I could feel my arousal growth and it began to pinch.
Caitlin kept pumping me. I have no idea for how long. I definitely feel arousal, but nothing like an orgasm or even ejaculation. Eventually, she stopped and pulled out.
“Okay, that is enough for now. I have to get running to work. Turn over.” She said.
I rolled onto my side and looked down. I could see that I had leaked a large amount of precum onto the towel, but there wasn’t any cum there.
“Just as I thought, it didn’t work this time.” She said looking at the towel. “It’s okay, I’m off during the day tomorrow. We can try again then.”
” Again? I thought you could help me…” I started.
“I will help you. Just relax. Sometimes it doesn’t happen the first time. I would stay and try longer, but I really have to go.” She interrupted as she got off the bed, removed her harness and began dressing for work.
“I’m out of work at 10 am tomorrow. If you’re available, I can stop by around noon.” She stated.
A little stunned, I responded “yeah, sure… I should be around.”
“It’s a date then.” She said with a chuckle. “I’ll leave the harness here. Be a dear and clean it up.”
“Okay.” I walked her to the door.
I cleaned up everything from her visit and got into bed. I felt even more frustrated than before Caitlin had shown up. Sleep did not come easily.
Part 10
The next morning I woke to a text from Tiffany: “How’s it going? Have you used the Christmas present I gave you? Called Caitlin yet?”
I responded “I did use your present, but couldn’t get it to work. Saw Caitlin last night.”
She sent back: “I’m sorry the present didn’t work. Caitlin is great, isn’t she?”
I sent back: “yeah”
I really didn’t want to get into the details of my encounter with Caitlin. As it was, I was concerned about her visit this afternoon. I really wasn’t sure that I wanted her to fuck me in the ass again. It didn’t work in the first place and it was uncomfortable and humiliating. That being said, I was about to crawl out of my skin in frustration. My whole groin hurt from the pent up sexual energy and I just couldn’t bear the thought of waiting until Tiffany returned for that feeling to go away.
I decided to try the prostate massager again. I figured if I could get it to work I could just tell Caitlin to skip our meeting. Unfortunately, nothing came of my second attempt to use the toy.
So, I waited and around noon there was a buzz from downstairs. It was Caitlin. I buzzed her up. Again, when I opened the door, she greeted me with a full body hug. I just couldn’t control myself and my penis strained against the device.
“Hey there! How are you doing today?” She started.
“Okay, but I’m more frustrated than yesterday.” I answered.
“I’m sorry about that. I’ve beenthinking about you and I think I know what the problem was.” She said.
“ha ha, I hope so.” I responded trying to keep myself in a light mood.
“Okay, lets got started. Go lay out the towel, put the harness on the nightstand and get into position.” I’ll be in in a second.
“Okay.” I said and left to do as she said.
When she walked in I was laying face down on the towel. She came of the side of the bed wearing nothing but her panties carrying her large purse. She stood near the nightstand, put down her purse, and picked up the harness. She just held it and looked at me and said, “That doesn’t look like the position you’re supposed to be in.”
I was slightly confused… and then it hit me. I lifted my hips up so that my butt was a bit in the air.
“Better. not quite right.” She responded.
Again, I paused a little confused.
“Arms.” She stated.
Without saying a word, I put my arms behind my back.
“Very good.” She said. ” So, I think the problem last time was one of size. I stopped by a shop on my way over and bought one that should work better.”
As she spoke I watched her removed the dildo that had been in the harness and saw her pull a much larger, realistic looking dildo out of her pursuit. The thing was about my size, maybe a little narrower. I immediately reacted. I turned to my side and sat up.
“Woah, woah. that thing is way too big. I can’t do that!” I objected.
Without stopping the installation of the new, larger dildo, she spoke to me, “I can understand your concern, but you shouldn’t worry. Women and gay men all over the world can accommodate something like this in their anus. You can too. Plus, I’m a nurse, I will be gentle and I won’t hurt you, I promise.”
By this point she had the new dildo in the harness and was putting it around her waist.
I remained sitting, and said “Caitlin, can’t we please just try it again with the smaller one?”
“It didn’t work. I know a bit about the internal male anatomy and the other one just wasn’t big enough to stimulate your prostate. This one SHOULD do it.” She said.
I still hadn’t budgeted, and said “I really don’t think I can.”
“Okay, okay. First of all, you can. But if you need a moment to relax, we can go in the other room and relax for a bit. Come with me.” She said as she reached out to take my hand. I let her lead me back in the living room.
She sat on my couch, still with that plastic cock jutting out from her crotch.
“I don’t have to work tonight, so I’ll have a beer. Get one for yourself too. Or something stronger if you think that will help.” She said.
I brought her a beer and I had one for myself. I sat down on the couch next to her.
Before, I could say anything, she said, “Tiffany told me you give great foot massages. I would love one.”
I feel myself moving to the floor in front of Caitlin. I set my beer next to me and took one of her feet in my hands and started rubbing it. The instant I held her foot in my hands and looked up at her almost nude body, those beautiful breasts and that dildo sticking up from her crotch, I began to strain against the device.
“So, tell me why you’re so nervous about this.” She started.
“Um… well, I guess I don’t relish the idea of being fucked in the ass at all. And that thing is big. And it looks, so… so…” I started
“Real.” She finished. “Yeah, a lot of them look like this. It isn’t really a big deal. Are you worried that it somehow makes you gay?”
“um… not really, but straight guys don’t do this” I answered.
“Actually, some do. More than you might think. Let’s try an experiment, stop rubbing and lean forward.”
I did as she asked and she scooted forward on the couch. The tip of the dildo was now just a couple of inches from my face.
“Kiss it.” She said. “It isn’t going to bite. It is just a piece of plastic.”
She just stared at me, waiting. I sawed. Then I learned forward and gave it the slightest little brush with my lips and made a kissing sound. My cock throbbed in its prison. At that she smiled and sat back and put her foot back in my lap.
“Now, let me ask. Do you feel like dating men?” She inquired.
“No.” I answered.
“I didn’t think so. You’re fine. You’re still a straight man. And I will be gentle with you. You have nothing to worry about. She assured me.
I continued to rub her feet and we drank our beers. She actually told me something that had happened during her night shift at the hospital. It was an ordinary conversation if you ignore the fact that I was on the floor in a chatity device rubbing the feet of a nearly naked woman wearing a realistic strapon dildo.
When we were both done with our beers, she pulled her foot away and stood and extended her hand. Without a word, I took her hand and stood. She led me back into the bedroom. She just stood by the side of the bed and I took “the position.”
“Good boy.” She said.
She got behind me and applied the lube. She went really slow when she began to insert the dildo. A couple of times I took a sharp breath and she would pause and encourage me to relax. Then she would continue pushing. When she was all the way in, she said “Down” and I lowered my hips.
This time she just laid on my back for a few minutes whispering in my ear. She told me how well I was doing; to get used to the fullness; that while it was a cock in my ass, it was attached to a woman and I was still straight.
After a little bit, she raised herself up and used her hands to pin my arms and shoulders down. Then she began thrusting. In a short time, she was thrusting with a fast pace. Because the new dildo was much longer each stroke was longer but each one ended with her pelvis slamming my ass. I could hear her breathing hard. I think I was moaning.
“That’s right. Be a good boy and take that dick.” She exclaimed.
I’m ashamed to admit it, but the dirty talk made me feel like I was going to burst out of the device.
After a bit, I could feel her start to shake and her breathing became heavier. Her pace increased. Then with one final slam into my ass she shuddered, moaned, and remained buried slightly rocking her hips.
“Oh, god that was hot. I just came.” She explained.
She remained on top of me for a couple of minutes and then pulled out and told me to roll to my side. I did and we both looked at the towel beneath me. I actually was so focused on her and the feeling in my ass that I had no idea what was happening except for the strain of my penis against its cage. As it turned out I still hadn’t cum. There was nothing but a spot of precum.
She looked up at me and said, “It’s okay, we’ll get it next time. Practice makes perfect after all.” And then she smiled.
I dropped my head to mattress. She stroked my hair and said, “You should be proud. Not many can take a pounding like that. I don’t think I could take it in the ass half as well as you just did. And you made me cum.”
“Thanks.” I said in as since a voice as I could muster.
“Your a sweet boy.” She said. “Take this off of me and clean it. I haven’t had a chance to sleep since my shift. I’m going to take a little nap here.”
I did as I was told and left her to sleep on my bed.
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