First time with an anal plug

I've always enjoyed ‘first time’ stories, so I thought for my first story I would tell one about one of my best first time experiences.
This isn't my first anal experience though… that happened long before (and I may tell that story someday too if this gets a good response from people). I had tried other anal toys before this, some of them were my own creation, but they were all fairly thin and small mainly just to get to my prostate for direct stimulation and that was it. This short story is about my first time with a thick plug and also the first time that my girl was involved. So I’ll start from the beginning…


I'm sure you've all had this experience… walking through a sex shop with your partner, looking and giggling at all the toys and products. Well my girlfriend Jenn and I were doing just that one random Saturday evening and stopped to look at some nice glass products we saw. I picked up a few dildos and suggested she get one to enjoy for days I wasn't around and she felt the urge. She thought about it for a sec and kind of shrugged off the idea. Then I saw the anal plug and picked it up. I looked at her with a grin and said “If you’re going to do ‘this’, you’re going to need practice”. See, we’d talked about doing anal a few times already and when I used my fingers there she seemed to enjoy it, but she was very hesitant to take me on since I'm fairly thick and just the thought made her nervous. So when I saw the toy I figured a little practising could stretch her out and get her feeling comfortable with the idea.

Jenn looked at the plug and said “No way! Look at the size of that!”
“Huh?? I think it's kinda small” I replied.

She took it from me and attempted to wrap her fingers around it, which was difficult with the type of packaging it had. “Look at the thickest part here” she said. “It says it's 1.5 inches thick. How much do you think I stretch down there?” What she didn't know is that I was secretly wanting it for myself as well, because I'd never tried something so thick and just holding it in my hand was turning me on.

“I don't know.” I laughed. “It says it's a medium size, I mean look at that one over there.” I said pointing to the far end of the wall where a massive 4 inch-wide cone was hanging.

“Well that's just disturbing. I don't know who could ever use that.” She replied. As she tried again to wrap her fingers around the plug she was holding she sighed “I don't know if I can do this one.”

I looked at Jenn's face while she imagined squeezing the hard, smooth glass into her anus and shivered a bit. I was picturing it too and felt determined to make it happen, for both her and myself. Our relationship was fairly young so at this point she was unaware that I had already began to explore my own sexual anal desires so I didn't know how to breach the topic. I had no idea how she might respond. She could think I was a freak or even think I was gay which would clearly be a problem for our relationship.

We stood in silence for a minute, both staring at it, contemplating the idea of this little glass wonder until I mustered up the courage to make my suggestion. I took a deep breath and said “How about this… I'll do it if you do it.”
She looked up instantly and replied “What do you mean, you’ll do it? Like… you'll use it too?”

“Yeah” I answered, “In fact I'll use it first. And if I can't take it then you don't have to try.” Obviously I had a secret agenda, since I'd wanted to try it all along. So I saw this proposal as the perfect opportunity to covertly suggest what I was secretly craving. But I was nervous as hell about what she might think and how she would react. Like I said, our relationship was still young and I really liked this girl, I didn't want to scare her away, but at the same time this could lead to some amazing experiences if she agreed.

Her eyes were wide with surprise as she looked back down at the toy. My heart was pounding with anxiety and fear. After only a few seconds she said “Okay!” Still looking down “If you can do it, I can do it” she supposed. Inside, I sighed in relief and then suddenly excitement started to grow for the night to come.

We kept the glass toy with us as we continued to walk around the shop, looking at other products we might be interested in and realizing we'd need a bottle of lube to ease the experience we were going to have. My anticipation grew quickly and I couldn't take it any more, so I suggested we just pay and go home. Only a ten minute walk away, home seemed too far… for me anyway. I think she was much more nervous than excited. But along the way we were both fairly quiet, which was rare for us. Anxiousness and nervousness will do that to you I suppose.

When we got in the door, we both immediately opened the bag and took out our new toy. She actually gasped when she was finally able to get the packaging off and fully wrap her fingers around the thickest part. “Babe” she started “It's as thick as you! I don’t know if I can do this.” She continued, echoing her initial thoughts in the store.

I took it from her and wrapped my thumb and index finger around it as she had. Just from touch, I could tell she was right, it was almost the same girth as my penis when it's hard. I've measured myself a few times, so I know I'm precisely six inches in circumference, which is apparently fairly large (if you believe the internet). In fact my penis is almost an identical length as well, so I'm 6 x 6, which I always thought was kinda funny. I'd always wished for a bigger one, but which man doesn't right? I suppose I have no problems with average length. I know my girlfriend doesn't, so that's really what matters. At least our new butt plug was only 4-1/2 inches tall, so that part didn't scare either of us. It was just the thickness.

We took out a measuring tape and wrapped it around the widest part of the glass. It measured 5-3/8 inches, so we were actually both wrong. It's thinner than my penis, but still thicker than the average. I looked at her and said “Well, it's our now. We can't return it, so we might as well just give it a shot!”

“Okay, but you're first.” She replied “That's the deal!”
I simply replied with a “Mhmm” and turned to walk towards the bed with a smirk on my face.

As we reached the bed, we both stripped down quickly and climbed under the sheets. This was certainly a different experience than any previous sex we'd had. We only kissed a little as my anticipation was growing through the roof. She tossed the sheets off us and saw I was already hard. Instinctively, she leaned down to put my cock in her mouth, since that was always her favourite thing to do, and realized after a few licks that there were other matters to attend to. She propped herself up on her elbow and asked me quietly “Do you want me to do it for you, or do you want control?”
“I think I'd better handle it myself.” I answered. “At least at first anyway.” I added.

She rolled over to reach the nightstand and grabbed the bottle of anal lube we'd also purchased. Shaking it in her hand, she popped it open and squeezed some onto her middle finger. Clicking the cap closed, so tossed it back on the nightstand and rolled back over to me. She positioned herself upright, sitting with her legs crossed.

“You'll need to open wide.” She said as she coaxed my legs open with her free hand. I was nervous and excited and hard as a rock. As she spread my legs I slid my hand across her thigh and lightly touched her clit with my thumb. That's when I realized how excited she was too when my thumb glided over her slick pussy. I'd never felt her so wet so quickly before, and it just made it all the better. Knowing that she was into it and totally willing to see and help this happen really let me relax and all my inhibitions started to leave my mind.

She touched the lubed finger to my anus and I took a quick breath from the cold sensation. With a smile she started to circle the hole, sliding around it ever so gently. She took her time and pushed slightly, breaching my opening just barely with her finger tip. My head back and my eyes closed, I couldn’t help but let out a warm “Mmmmm”.

“I had no idea you'd be into this.” She said quietly. I opened my eyes to see her smiling and staring at my ass with concentration. “But it's so hot!” she continued. That was it. All my worries were now gone completely, knowing that she was enjoying what we were experiencing together.

As my thumb continued to slide around her clit, her middle finger continued to probe further into my ass. Firmly now, she had begun inserting more and more. She curled her finger slightly and started pumping in and out. Then suddenly without warning she stopped. She slowly removed her finger and continued circling the hole as she had done in the beginning. With her free hand she took my hand off her body and moved it over to the toy we had lying on the bed between us. Without words, I looked in her eyes and she gave me a slight nod with a smile. I took the glass plug in my hand and shuffled my legs open even wider. I noticed her move briefly, I suppose to wipe her finger clean with a Kleenex from the nightstand. But I was far too engrossed in what I was now doing to say for sure what she was doing at this point. She laid down beside me now and caressed my chest while I kissing my neck and cheek. It felt amazing in tandem with the glass now circling my anus.

I moved it slowly at first and somewhat copied what she'd done with her finger. As I started to push, I realized even the tip was thicker than her finger and when it breached my hole I closed my eyes and sighed. It actually slipped in quickly for a moment since the glass was frictionless with the lube. I removed it and repeated the motion. Slower this time it started to slide in. Bit by bit, I was pushing up towards my stomach. As it got wider and wider I could actually feel my anus stretching. Trying my best to relax I kept pushing ever so slowly. It was only half-way in when I stopped and had a moment when I felt I had to ‘reset’. So I squeezed my ass tight and pulled it out completely. By this time Jenn was now kissing my chest, licking my nipples and stroking my hard penis, but still quiet and supportive. I still had my eyes closed, but I heard her whisper “Please don't hurt yourself babe.” After a few hard squeezes of my empty anus, I was ready to continue.

With a quick breath, I pushed on my opening with the toy again and it made a much smoother entrance this time. I started gradually getting it further and further and now I could really feel the stretching. I had to start slowly pumping it in and back out slightly, then further in and back out slightly. I continued like that as it got closer to the thick base. There were a few moments where I had to hold it in place and take a breath. It was starting to become a really intense feeling as I tried different motions to easy the stretching. I twisted it in my fingers while I lightly pumped it in and out. Then I figured I had to just go for it, so I took one last breath and firmly but slowly pushed for the goal. It was an odd combination of pain and pleasure when I felt my anus expand to what seemed to be its limit. Then suddenly, the toy got past its widest part and just popped in completely. It happened so quickly that the tip of the glass hit my prostate and I gasped loudly. My eyes shot open and I looked at Jenn. “It’s in.” were the only words that could come out of my mouth.

“No way!" She said as she jumped up on her elbow and looked for herself. Her eyes wide, she looked back up at my face with a big smile and then turned back to quickly swallow as much of my cock as she could. With my rock hard member deep in Jenn’s mouth and a solid glass plug deep in my ass, I was in complete heaven.

As she moved her mouth around my cock she motioned to take control of the toy. I removed my hand and she began to gently twist it with her fingers. It was no longer touching my prostate (it only did that at the initial entry), so I whispered for her to push and she did. The toy seemed to be just barely too short to touch the prostate while sitting in naturally, but as soon as she added some slight pressure I could feel my insides rejoicing. I couldn't believe the experience, the pleasure. As she continued to twist and push and pump the toy I began squirming in ecstasy. All that and at the same time she had me in her mouth. It was unlike any blowjob she had given me before however. It had always been her specialty in my opinion, but this time she must have been concentrating more on my ass than my cock as she was simply holding me deep in her throat for the majority of the time. Since she had no free hand to use she would pull her mouth up the entire length of my cock and then immediate slide it back down again, practically swallowing it entirely. She is an absolute expert and it was absolute bliss.

While I continually felt the pressure on my prostate and the mouth around my cock I started to lose all control. My body was sweating and I started writhing from the sensations. I heard her moaning as she could tell I was clearly close to orgasm. I'm sure it was only minutes, but it felt like an eternity of paradise. Then it came to an abrupt end when I simply had to let go and erupted in her mouth. As I was letting go, pumping spurt after spurt in her throat, Jenn was pushing hard on the toy giving my ass all it could take and applying the greatest pressure my prostate had ever had. I could hear her moaning again as she tried her best to keep my cock in deep in her mouth with my hips bucking and my cum flowing in her throat.

When it was over, she released the pressure on the plug, but kept my penis in her mouth a while longer. She continued to moan while her head slowly bobbed on my shaft, waiting for it to soften slightly. When she was ready, she slowly slid her mouth up my penis, careful not to spill any cum along the way and kept her lips tightly closed around the tip as she swallowed twice. At this point I had my eyes open, watching the master at work. And in the aftermath, I concluded that it had been by far the most intense and amazing orgasm I had ever had in my life to that point.

Of course there was still the matter of the plug in my ass. As hard as it was to get in, I thought it could be just as hard to get out. Contrary to that however, it popped out quite easily after a short push of my muscles and a slight tug on the base. While it did stretch my anus to its max again on the way out, it was far less painful this time and by this point felt quite relieving to get it out.
I simply reached over and put it aside on the nightstand and then lied back in complete relaxation. Jenn was again lying beside me caressing my chest as she did earlier, and she kissed my chin and said “Thank you for sharing that with me.”

I looked in her eyes, amazed at this wonderful woman and said “No, thank you!”

I started to glide my hands over her body and ended up between her legs (of course), where I discovered just how much she had enjoyed the experience. She was literally dripping down her legs from her own excitement. I pulled my glistening fingers back up to my mouth and licked them clean. She gave me a coy smile and grabbed my face to kiss me deeply. I rolled on top of her and started grinning.

“Well I did it.” I said. “So you know what that means… now it’s your turn.”





The End.
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Categories: AnalFirst Time
Posted by FearlessAddict
2 years ago    Views: 1,021
Comments (10)
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10 months ago
reread it with a boner in my hand. would have been better if she was watching your ass and the plug going in. otherwise, terrific
1 year ago
excellent, as your other stories are.
1 year ago
Nice story.
njguy2008
retired
1 year ago
great story! made me cum
2 years ago
great story
2 years ago
Beautiful erotic story!
2 years ago
Great story. I like that she was really into it. I believe that a lot of women are into it, but they are afraid to broach with their men. I believe it is also the same for men. Well, at least you weren't afraid to bring it up - and look at the reward.
2 years ago
Thanks for the comments.
Yea she let me do it not long after that, but only a few times since then because she says it hurts too much. Ahh well.. not much I can do about that.
2 years ago
Great story! It was well written and really capture the experience. I wish all women were this excited about exploring like this.
2 years ago
Nice, Tell us more of you bouts with her, did she finally relent and allow you to pleasure her anal orfice?