Sandy's Story - No Longer an Anal Virgin!

I've been helping a young couple, Sandy and Tom, with coaching on how to get vanilla Tom to satisfy spanko Sandy's cravings. Sandy had requested I provide the couple with some coaching on how to get Sandy fucked in the bum by Tom, something they had not tried before. After some good-natured teasing, I was only too happy to help.

I sent the couple an email that I reproduced in Sandy's Story - Anal Sex, giving them some step-by-step instructions on how to prepare and how to do it. Tom and Sandy did that, and sent me their reply. Here it is.

Hi Julie,

I'm no longer a bum virgin. Yay. Tom stuffed his cock deep in there and pumped away until he splooged right up inside of me. It hurt, but in a good, spanko, sort of way. He now has another addition to his "toolset" for when I'm a "bad girlfriend" 😉.

From your shopping list, we already had vaseline and lube and some mild natural liquid soap. I also had a smaller-sized dildo, but not a realistic Tom-sized one. Unfortunately, my local drugstore did not have the enema bag 🙁 so we ordered it off Amazon, and since we were doing that we ordered everything else off there as well. Tom was not comfortable taking me to a sex shop and discussing having anal sex with me that openly with a live stranger.

I've attached screenshots of the stuff we bought. All one-day delivery. It was kind of exciting ordering it and then getting the brown boxes from Amazon dropped off on our doorstep, knowing what was in them, bringing them in, opening them up, examining them, cleaning them, and storing them away. It's all going up my butt, and then Tom is going up my butt. Scary but exciting, sort of like a hard spanking.

We had something planned for Saturday already, so we waited until Sunday afternoon to play.

We started with the enemas. Never done that before.

I figured it was more on me, so I got everything ready to go, including filling up the enema bag with a squirt of soap and warm water. I filled it up to as much as the bag would take, knowing I would regret it. I tested the flow and everything, and hung it in the bathroom on the shower curtain rod with a bent wire coat hangar. I put some pillows on the floor and covered them with towels. Then I went to get Tom. Pretty daringly, I thought, I got completely undressed and then went to get him where he was sitting, and told him I was ready for my soap-water enema. I hoped it would turn him on when he saw me naked and submissive like that. [Tom says: it definitely does].

He smiled at how naughty I was and took me by the hand to the bathroom. I pulled back a bit and told him I had changed my mind. He smacked my bare bum and said that was tough, because I was getting it one way or the other. He made me face the bathroom mirror, he held me there with one hand, and he smacked my bum with the other over and over again telling me that this was going to happen whether I liked it or not (I told him in advance I was going to act reluctant, which was not much of an act, even though I ultimately wanted it, and that he should "make me").

He made me get on all fours over the pillows. I put my head down on the ground and my bum up in the air for him. He had studied your email, Julie, so knew exactly what to do every step of the way. He loosened me up with lube and a finger. So embarrassing. My girl parts all out on display as he did that, and I felt myself getting excited (I was already excited, truth be told). He then vaselined the bit around my anus and a bit inside as well. He tested the flow for himself, used the lube on the enema nozzle, and then gently put it inside of me. It got stuck a bit halfway in, and I reached behind myself to get just the right angle and pushed it all the way in.

Tom then started the flow. At first it felt like nothing was happening at all. But then, not too long into it, I started cramping a little and told Tom. He stopped the flow and gave me a little belly and pussy rub. Then it was better, but I for sure felt something in there, and started to feel a bit like I needed to go, but not really. He started up the flow again, and this time I felt it a bit sooner, but also held on for a bit longer before asking him to stop. We did this several times. Each time afterwards the cramping subsided pretty quickly. The pussy rub was a good idea. It took my mind off it. I could also feel my low belly starting to distend. Both feel it internally, and feel it by touching it on the outside. Towards the end I felt like I really, really needed to go, and felt I had to clamp my bottom hole tightly around the enema nozzle to stop from spurting out my back hole. Tom announced I had taken the whole bag. I measured it afterwards. It's about 2 liters.

By this time I felt a lot of pressure at my backdoor wanting to get out. Tom lubed up the small butt plug. He pulled out the nozzle and pushed in the plug. I felt a sharp pain as he pushed it in that soon subsided. In between, I squirted a bit of dirty water out my bumhole. Tom scolded me for that and swatted my bum. Even with the plug in, I got the feeling it would shoot out and right across the room like a champagne cork, so I put my hand back there to keep it pressed in. Tom had me stand. I was directly facing the toilet. I needed to go so bad. "Five minutes," he declared. I swore to Tom I couldn't make five minutes and begged him to let me go now. He was adamant, though.

[Tom says: Couldn't care less. It's what she wanted.]

I felt ridiculous holding it like that for the full five minutes. I was literally doing the potty dance, just like you said I would. I kept begging Tom but he kept denying me, giving me a countdown of the time left. When I was at the four minute mark I knew I could last the five, so just gritted my teeth and went for it.

"Time's up," Tom said. "you can go now."

"You're going to leave now, right?" I asked him. That was what we had decided.

"Nah, I changed my mind," he said.

[Tom: I had always intended to "change my mind" - was wondering if I would get the safeword and kicked out. Nope. I don't get grossed out. It was fine.]

I begged him to leave, but didn't use my safeword. But I couldn't wait any longer, so I sat on the toilet, kind of on my arm, pulled the plug out and then just GUSHED. It was such a relief. But so embarrassing. But such a relief. It got real smelly real quickly and I flushed as soon as that happened. But it just kept spurting and spurting out. Just when I thought I was done, another big extended spurt came out. I was moaning at the feeling like, really bad diarrhea.

Meanwhile Tom had taken the plug and was washing it in the sink. He also rinsed out the enema bag, cleaned up the nozzle, and refilled it with just warm water. I was just collapsed on the toilet seat, dreading the next one. Little spurts coming out in 10 second intervals. Tom lost patience with me and said, "Let's get you rinsed out."

I was ass up again for the second time. Tom repeated everything he did the first time, and emptied the full bag into me. Based on your email, we weren't sure if you intended for him to keep me standing for another five minutes afterwards, but Tom decided I should regardless, despite my complaints, and so he did. We did that twice in a row, and the second enema was pretty clear but still had bits of stuff, so Tom gave me another half enema, like you said, and didn't make me stand for that one, and that one came out completely clear with no smell at all.

As you said I would be, I felt completely rung out after all that. It's like you've done this before 😊. We had me rest on some towels on the bed for the next 30 minutes. Tom left me in peace. At first, I had zero interest in doing anything sexy. I just felt, well, rung out is the best word for it. A little exhausted from the experience. But over the course of the 30 minutes, I sort of re-lived the excitement and the embarrassment of what had just been done to me, and my pussy started coming alive again. I had read stories online about girls being punished with enemas, and I felt like that.

Tom came in and caught me rubbing myself, so he declared that I must be fully recovered. I agreed. He took me to the bathroom for a final wash up "back there". He had me kneel with my head down in the tub, and used the spritzer and soap and a washcloth to give me an extremely thorough scrubbing of my bumhole and my pussy. I complained because he was a bit rough with me with the washcloth and he just didn't care, which sort of thrilled me. I felt a bit like a baby being cleaned like that. He rinsed me with a final hot water spritz which felt absolutely delicious. I remember pushing my pussy up to better direct the stream of hot water where it would do the most good. Tom indulged me for quite some time like that. He then took me out of the bath, helped me to dry off, and took me back to the bedroom where the deed was going to take place.

First we were going to use the small and medium plugs from this set:

It's the "naughty 1 trainer" from Doc Johnson.

The three plugs are 3/4" wide, 1" wide, and 1 1/4" wide.

He decided to sit on the side of the bed and take me across his knee, which was exciting. He had the lube and the plugs. He started with the smallest plug, which was 3/4" and got that one in. I had already had that one in me, and it was not so challenging to take. It still hurt a bit going in. He fucked me a bit with it, including pulling it all the way out and all the way back in again. After a couple of those it no longer hurt going in at all. He then let it sit while he gave me a spanking. I wasn't expecting a spanking. But it was nice to get it. Getting spanked with a plug inside is a new sensation. Every spank seems to jiggle it around in there. He even lightly spanked the base of the dildo, which I definitely felt as well.

He then swapped it for the medium plug, which was 1" wide. That one was a bit of a struggle getting in. I needed to push as if I was going to the toilet, which was a weirdly hard thing to do at first, but I got used to it. Just when I thought I was going to rip open it popped right in. Once it was in, it was very bearable. But the going in was rough. Tom fucked me with that one a bit. I begged him not to take it out, but he did, which was painful, and then re-inserted it, which was painful again, but nothing like the first time. He let that one sit inside of me and gave me another spanking.

Before moving on to the largest butt plug, Tom was going to give me the vibrating butt plug. This is it:

It was about the same size across as the medium plug.

It has various vibration modes. Tom put that one into me next and switched it on. The plan was to keep that in me for a more extended period of time to loosen me up, as you suggested, Julie.

The new Tom-sized cock was out and sitting there on the bedside table. This is it:

When we were shopping online this one really caught my eye. I instantly felt super embarrassed just seeing it pictured there. Tom is about 6" or so and about the same width around. And the "dual density" promised to be soft on the outside and hard on the inside. It was "Molded Directly from an Actual Erect Penis". I'd really literally be taking some other guy's cock inside of me. It was "Hand-Detailed to Capture Every Vein, Bulge, and Crease of a Real Erect Cock." I felt so embarrassed choosing that, especially when Tom asked, "is that really what you want?".

When we got it, it was not quite as realistic as the photo made it out to be, and a slightly different colour, but it was pretty close. We're calling it "The Doctor".

These are its dimensions.

With the suction cup I imagined doing timeout with my mouth around it up against the wall. Julie, you recently posted a pic suggesting that on your Thoughts on Sexy Images post (when you post this, can you please include that pic?).

Can you even imagine having to do timeout like that? It's like killing two birds with one stone. You're both being punished, and you're learning to get even more comfortable giving deep head.

I asked Tom in advance if I could do timeout with the cock in my mouth. He declared me a very bad girl but allowed it. He decided I'd be kneeling this time. So there I was, kneeling on the ground going down on the big dildo suction cupped onto the table, while the butt plug was vibrating. He sentenced me to 15 minutes! I raised up and started saying "noooooo", but he pushed my head back down onto the dildo and said "I don't care."

So there I was getting buzzed in the butt for fifteen full minutes with my mouth stretched around the big dildo. It amused Tom to have me practice giving head to the dildo. "Let's see how deep you can go. Good girl. Now lick it, all the way up and down. Lick the balls. Ok, suck it now. Bob on it like a little porn star. 'Atta girl." Tom said all of this sort of absentmindedly as he surfed on his tablet. Julie, I must say, you've done a great job on Tom.

Tom declared my timeout up. The muscles around my mouth felt a bit sore. It turns out my bumhole had gotten quite loose, though.

So next came the big butt plug. It's 1.25". Surprisingly, I took that one relatively easily. I pushed like going potty. I felt as if I was tearing a bit (but knew I wasn't), and in it popped. Tom insisted on removing and re-inserting even this one, which I thought was a bit unfair of him.

Next you said Tom should use my thinner didlo. He did. It was super easy going in, barely felt it. But it was a bit longer, and I felt it in deeper. There was a very sharp pain when it pushed in a bit too deep. But together we coaxed it back in deeper and deeper until it was comfortably all the way in.

Next was "The Doctor". The new dildo that my mouth had become so comfortable with. It's kind of an close resemblance to Tom in size and shape. The texture is nice. Kind of squishy on the outside, harder core on the inside. For this, Tom had me across the pillows on the bed. He put back in the medium plug, gave it a few ins and outs, and then put in the large butt plug and did likewise. Then came The Doctor. I felt the tip pushing against my bumhole, and it seemed like there was no way that was going in. But he just kept gently pressuring it. And me, I kept breathing and pushing as if going to the potty, and then all of a sudden, bang, and the tip was all the way in, which sort of took my breath away and made my eyes go wide. I imagine it was just like that girl you had the final gif of in your Sexy Images post. Put that just here when you post this.

That was me. As in, "oh my!". I just kept breathing as Tom slowly worked it in and out and in and out.

I thought it was getting to be a bit much by now, and I would rather have Tom inside of me rather than doing this, so I told him, "now you". Tom was already really hard. I guess he liked the idea of ass fucking me. [Tom: I did]. We got on my side with my knees up, and Tom spooned me as you suggested. Put that drawing here.

And I did reach back and part my own butt cheek as you said. Tom added lots of lube into both me and onto him, and then he pushed the head of his cock up against my butthole. It was just like the big dildo, but better. More squishy. More warm. Hotter in the sexy sense. And just way, way, more submissive.

"Please push it in," I begged him.

"Are you ready?" he asked.

"Yes".

He applied a bit more pressure and I breathed and tried to open myself up by pushing into him and dilating my bumhole muscles, and then he was in.

"Oh God. Oh I love your big dick in my ass," I told him.

He started pumping and I dove for my clitty and started rubbing. I kept up the talking, telling him how much I loved him fucking me in the ass. I even asked him to fuck me harder. I was excited. I actually orgasmed with his cock inside of me as I rubbed myself. And then it was, hang on, because Tom upped the pace and pretty soon after came into my backdoor. He pulled out with a pop and I was no longer an ass virgin.

I was so goopy back there, and around front as well, but Tom "made me" put my panties right back on, and I got to feel the squishiness right up until bedtime, at which point Tom had mercy on me and said I could take my panties off and wipe myself. He gave me a pretty good bedtime spanking after I came back so I had to go to sleep with a sore red bottom. He's been giving me bedtime spankings out of the blue. I love you Tom. [Tom: I love you too.]

The bum sex and all the prep was really fun. I thought it was going to hurt more. Sure it hurt, but a good hurt, like a spanking. And so naughty, just the whole thing. And I was so clean back there that there was no mess on anything at all. Being that clean back there gave me a lot of confidence to just go for it, so thank you for understanding that. I think I'll be comfortable doing a bit less in that regard next time (more along the lines you previously indicated), but Tom now has the "punishment enema" for me as well, which will be a nice addition to roleplay every now and then.

Thank you for this, Julie, and for all your help along the way. Tom is feeling very comfortable in his new role, as am I. Been noticing a few "everyday" dominant tendencies in him as well lately. In addition to bedtime spankings, been threatened with a disciplinary spanking more than once already. [Tom says: fringe benefit].

Tom and I are going to make up a roleplay of our own for next time, and I'll write to you as to how it goes.

Thank you thank you thank you thank you!

Sandy (with Tom)

Aw shucks, that my pleasure you fun kids you!