After the events of [Episode 2](https://www.reddit.com/r/eroticliterature/comments/ipmf3h/enter_by_the_exit_episode_2_anal_fingering/), which happened on a Sunday afternoon and evening, we went through what had become our usual Sunday evening routine. Shower separately, get dressed, order food, eat and then I leave once the evening rush of people out for their runs, walking their dogs and shopping had died down a bit. By this time we were not maintaining strict and sitcom-like secrecy, but neither of us saw any reason to give people cause to gossip more than was unavoidable.
The only difference this time is that through dinner, every now and then we’d grin at each other like a couple of schoolkids who’d just secretly made out for the first time on a field trip. As I hugged her goodbye, I said “There’s a lot more where that came from”
“There had better be!” was the gleeful response.
The next day I got a text from her while we were both at work. It was the usual text one of us would send the other on a Monday or Tuesday: “This weekend (wink emoji)?”
“For sure” I replied.
Normally that would be the end of it until Thursday or Friday, when we would confirm or cancel, and firm up time and place (which was usually always her place). We never ‘sexted’ during what I now call the vanilla-phase. But now I could see that she was typing…
“I can’t wait to try ‘that’ again…”
I started to get a hard-on immediately, and replied “I can’t wait to try more!”.
I got a smiley back from her, which told me all I needed to know since she only ever used the wink and the smiley.
By this time the memory of the sight and feel of my finger in her ass was so strong I could almost smell her again. I hurried off towards the office bathroom, got there, yanked it out and in about two minutes, came into a wad of tissue in my left hand. I washed up, and got back to work. A few minutes later I was fully flaccid again, and the ‘post-cum’ leaked out. I decided not to bother with it and just cleaned up when I got home that evening.
During the rest of that week I didn’t hear from her, and I didn’t text, but I jerked off like a 90s teen with a few hours alone at home with a borrowed, scratched porn DVD that was circulating around the school. I guess a part of me always will be that teen. In the evenings at home, I got out older hard drives from the days – only a few years ago – when I compulsively downloaded porn and never watched 90% of it. I didn’t have to look for any anal scenes because I only have anal scenes. I did look for all the MILF and mature scenes I had though, watching a few minutes of each, thinking of her as I watched Alura Jenson getting buttfucked by three impossibly well-hung black men.
On Thursday she asked if I could come over on Friday evening, which was always a sign that she was horny, though she never needed to say it. Only this time I knew we would be exploring new territory, so the next evening I was at her door practically as the clock in her living-room was striking seven. Once I was through the door, we hugged and kissed like we normally did, and headed for the sofa.
But once we were on the sofa, at the point when we’d usually have our ‘hello’ quickie, she pushed me away and said “Let’s talk”
As I’ve described before, the wall between us was down, so I knew this was going to be a discussion about possibilities rather than limitations. I settled back and said “Sure!”.
She looked at the coffee table and said “So you’re an ass-man… I always thought you were a tit-man”
And then, brothers and sisters, I talked for twenty straight minutes. I know because I was facing the clock.
I spoke of how visually I had always been a breast-guy, practically since puberty and still was. I spoke of how as the girls in my friends circle matured and developed hips and rounder asses to go with their newly grown tits I found myself fantasising about their asses in private, while still hoping for a down-blouse peek while actually in their presence. I told her about the basketball game when I was around 14 where my friend’s older sister yelled “Double dribble my ASS”, and that night, thinking about her plump, nubile ass, I realised that what I really wanted was for my skinny young dick to be in her asshole. I didn’t even know if that was physically possible, or if anyone in the world had ever tried it, I just knew it was what I wanted, and I never felt any private shame about it.
I spoke of my thrill at discovering that anal sex was a real thing. It happened during one of those awkward group porn viewing sessions that guys did in the 90s and early 00s. All of us crowded around a 14″ CRT monitor, hoping that the DVD wouldn’t be scratched too badly. How the last scene in the movie was an anal one, and how all the other guys yelled “Gross!”, made retching noises and covered their eyes. I said nothing, but I made sure I kept that DVD, which wasn’t too hard since it happened to be my house and my computer.
I spoke of how I discovered that anal fingering and analingus were things and things that I filed away in the ‘must-try’ section of my brain. Of Ass-To-Mouth and how though I realised how much preparation porn-stars put into scenes like that, I would still love to try it. Of how I didn’t find it off-putting in amateur porn if there were a few stains on the guy’s cock or in the creampie, but I had found my own ‘hard-stop’ in scat, and was not into it or willing to try it. At that point she cut me off, laughing and said “We’re on the same page there, I promise!”.
The last few minutes of my monologue were me waxing philosophical about repression and my anal fetish. Of how I felt when all but one of my exes gave me flat ‘nos’ to my suggestions or allusions to anal, and how my sexual interest in them died a rapid and natural death after that. About the butt stuff I DID get to do with my most recent ex. Eventually I realised that I had run out of things I wanted to say, and I abandoned the declamatory tone I found I had adopted, and ended with a shrug and a “Yeah… so that’s what’s up with me and asses”, and settled back into the sofa, wondering how she was going to react.
(Weeks later she told me that she had wanted to laugh at several points during my speech, but could sense how cathartic a moment it was for me. I realise now, looking back, that despite my marginally greater sexual experience, this was a sign of her greater maturity and empathy, and I thanked her for it then, and still do to this day.)
“Well I’ve always had a few butt fantasies, ever since I was first married. But you should know what noone really talked about it in the 80s, when I was a newlywed.”, she began. She told me a little about her late husband, which she never had before. How they’d had a good marriage, good sex, but were never too adventurous in the bedroom.
“Even when I thought objectively about my own anal fantasies, I knew at the time that I didn’t actually want them to become real. My husband did suggest it once, but I brushed it aside”
She told how after he died, and after she had got through her grief, she had started to masturbate more regularly. How her fantasies involved increasing amounts of anal sex and anal play. How she discovered that she enjoyed erotic fiction where rich, powerful men forced young women to have their asses plugged and fucked. But how she still felt they were fantasies that would always be better if left in the fantasy world.
“But now there’s… us”, and this time it was her turn to look at me expectantly.
I took hold of her hand, stood up and took her to the bedroom. As we passed her dressing table, she grabbed something and chucked it onto the bed. I looked at it before I turned back towards her – it was one of those small flip-top containers of Vaseline. We were both more aggressive than usual with each other. She dug her nails into my neck and back. I pulled her dress up over her hips and smacked her ass harder than I ever had before, which just made her bite down on my lower lip. Her buttcheeks jiggled from the slap, and I watched them from over her shoulder. For the first time, I saw the signs of aging in her body not as things to ‘get past’ but as attractive in their own right. How she was just a little plump, giving her small love handles and big, globular buttocks. How they were sagging just a little bit, but that only made them jiggle more from my spanking, which I was doing quite vigorously at this point. I took hold of the rear waistband of her panties and yanked up on them, so they disappeared between her cheeks, practically turning them into a thong.
By this time she had already popped her tits out of her dress and I fell on them. Sucking on her nipples while I fumbled in her crack, now trying to get behind the panties I had just bunched up in there.
“Vaseline!” she hissed at me.
I turned, found the container, managed to get the damn thing open with one hand, and plunged in a finger, getting way too much out. I didn’t care though. I finally got her panties down, smearing excess Vaseline over the backs of her thighs, and with just the briefest pause to rub some of the lube around her pucker, pushed my finger into her backdoor for the third time. She moaned, and cradled my head with one arm while I was clamped on her right nipple. Her other hand went down and she started rubbing her clit.
This was another first, she had never masturbated in front of me, and I only had in the sense of pulling out of her and finishing myself off.
I had a good idea of where we were going to go by this point. I sat down on the bed in front of her, and licked her clit for a short while. She obviously stopped fingering herself while I was doing this, and put her hands on my head. I could hear how heavily she was breathing. I pulled my finger out of her ass, and pushed her down on to the bed. She briefly struggled back up, needing to unhook her bra. I got my jeans off, not bothering with my own underwear. I just pulled out my cock and started smearing it with Vaseline.
She saw what I was doing and gave me a half-fearful smile. “Are we really doing this?” she asked.
“I think you want to as much as I do”
She looked straight at me and said “Stop if I say ‘stop’, okay?”. I held her gaze and nodded once.
I raised her legs up and rested her calves on my shoulders, but then realised that her big plump ass wasn’t opened up in that position. I spread her knees apart and told her to hold onto her legs. I got hold of my cock – I could see pre-cum had already washed away the Vaseline on the tip – and guided it towards her asshole. When it was on her anus, I moved it up and down a bit, smearing the Vaseline on and around it, and on the inner surface of her buttcheeks. I started to push, and then heard a sharp intake of breath from her. The head of my cock started to slide in, stretching her pucker, but she clenched hard involuntarily and I popped out again.
I looked at her face, she was completely still and looking straight at me. Again thanking my stars for my small amount of real world anal experience I told her “Strange as it sounds, you have to push out when I’m trying to push in… that will allow me in”
“You mean like when I’m….” She gestured with her face towards the bathroom door.
“Yes, but don’t worry. Trust me.”
I didn’t wait for a reply, because I still leaking pre-cum, and was desperate now. I placed the head against her perfect brown asshole again, and pushed. First nothing, and then she must have started to push too, because her sphincter suddenly relaxed and I was sliding in! She gasped, and then squealed a little. Inevitably, she had stopped pushing and the involuntary powerful anal contraction started. Which felt great to me but was obviously hurting her.
“Push!” I said, urgently. “Push and then try to relax slowly”. She did, and I could feel the pressure lessening, and her face relaxed too.
“No more than this today, please” she said, almost in a whisper.
“Of course” I replied. The bulge of my head was comfortably past the rim of her asshole, and I wasn’t going to pop out.
“Kiss me” she said, reaching out with one arm. I carefully lowered myself down onto her, not wanting to slip out of her tight ass that was now MINE. Lips locked together, I rocked my hips back and forth almost imperceptibly. I could feel her relaxing beneath me, and soon her sharp breaths changed to “mmmmmmms” of pleasure.
I carefully manoeuvred myself back upright, and looked down at her, with her big breasts, bruised from my suckling, her wet pussy with its short bush, and her now just barely defiled asshole.
“I want you to touch yourself” I told her.
Smiling, she put her head back, closed her eyes and began to rub her clit. At first I just watched what she was doing, half in complete horniness, half in interest, trying to see what exactly she did to her own love-button. With her free hand she was tweaking and scratching at her nipples. After a few minutes I could tell she was on her way to cumming, and I couldn’t maintain my own immobility any longer. I knew I couldn’t risk ruining her experience by actually fucking her ass right now, so I just reached down and started wanking. It was the best wank I’d ever had. When her hand hit mine for the first time she realised what I was doing and just said “oooohhhh YES”.
In real life people don’t always cum together and this was one of those times. I briefly thought of trying to hold back, but I knew I was too far gone. If I took my hand off my cock only a ruined orgasm was in store for me. I sped up instead, and had the best self induced orgasm I’ve ever had before or since. Since I wasn’t at all far up her ass my cum started leaking out around my cock immediately.
She felt it, and moaned louder, and arched her back, raising her hips off the bed. I followed with mine so I would stay in her ass. Seconds later she began her now familar shuddering, went silent, stopped her fingering and pressed her thighs together. I could feel her convulsing, and her ass clenched so tight that it popped me out, followed immediately by what had remained inside her of my load.
When she finally relaxed and lowered her hips down onto the bed again, I realised she had been holding her breath. She was now panting. She reached out to me, and I lay down beside her.
“We can’t really call that full anal sex, can we?” she asked when she had caught her breath.
I thought for a bit. “No, but I think it definitely counts as an anal creampie”, I said, grinning.
Source: reddit.com/r/eroticliterature/comments/iq2n0j/enter_by_the_exit_episode_3_anal_first_timer_anal