Chronicles of the Special Stretch

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My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn’t know if we’d ever be able to have anal sex unless I went through some “anal training” first and I didn’t know if I really wanted to do that or not. He has never been pushy about anything sexually and said it didn’t matter, and that he loved me just the same, with or without anal sex.

After reading up on the subject, I realized that some of my “getting too stretched out” concerns were unfounded and that it really was a little like yoga in that you have to work at stretching a muscle to get it to comply with your wishes—whether it be to do a downward dog or a doggie style—it takes consistent stretching.

I decided that I might even like it and that I loved him enough to at least try. After all, I always loved it when we are fucking doggy style and he stuck a finger up my ass while I used my vibrator on my clit. That would always send me over the top—to the moon and back! So, my “special yoga” stretching sessions began.

This is the true-life diary of my two month ass-training for the man I love.

Day 1, Stretching session

(About September 15th)

I opted for coconut oil instead of KY because I had found it to be superior as a lube. Plus–bonus, he can eat it, it tastes good, and it makes your skin soft! I laid on my back on our bed—hours before he would be home. I think to myself that if I am able to accomplish a wide enough stretch to actually have anal sex with him, he’s going to be ecstatic! I wanted it to be a surprise.

I clipped my nails short and found my tiny little ass opening with a lubed up finger. I gently pulled aside the rim of my ass and softly worked the finger in. Ooo…it felt really good and I got an immediate tingling up through my pussy and clit.

The opening was so terribly tight, I could hardly move my finger, but I pushed it in as far as I could. I wondered how deep the cavity went and if my lover could get in “balls deep,” as he says. I try not to rub my clit, as I’m not here to pleasure myself, but to “workout” for my man. I can hear the conversation now, “Mongo, my love, I’ve taken up yoga.”

“You have, Angel? How far can you stretch?”

I would bend over, pull my panties to the side, and open my ass cheeks and say,

“Just far enough for you to fuck my tight little ass, my love.”

As I brought myself back to reality, I used my finger to pull the impossibly tight muscle to the left and to the right. The pulling was a little uncomfortable, but not to the point of pain. I thought back to the some of the porn movies I’ve seen where the woman doesn’t even blink when her the gigantic dick is shoved deep in her ass. Apparently this is achievable, just not without some ass training, I mused. I had read that if you clench down with the ass muscles over and over you essentially wear it out and then pull and stretch side to side. I did this for about 30 minutes with minimal discomfort. My clit liked the occasional attention I gave it too.


—I lubed up a few fingers because I wanted to try going further each time. After gently inserting, clenching, pulling for a few minutes, I was able to pull with my index finger wide enough to feel air, and I gently slid another finger in alongside the first. I had made progress in only two sessions. I can imagine the sight, me laying on my back, both hands under my back and buttocks.

My asshole was impossibly tiny and tight, and the fingers felt as if they would go numb from the tightness. I gently pulled and tugged in opposite directions, while my clit began to charge up. I considered inserting a butt plug and jumping my man when he comes home, but reconsidered, as my little tiny asshole was tired by the end of this session.

Session —I started on my back with two fingers, and my left thumb accidentally brushed up against my clit—-ohhhhh this felt so divine. I pulled my knees up to my ears and felt how the opening of my ass gets tighter around my two fingers with my legs in this position. I can’t wait to surprise my lover—and knowing what the feeling is like from the inside, I know he is going to go crazy over this super-tight feeling.

I wiggled off the bed and sat kneeling on the floor, knees far apart and fingers still up my ass. My pussy was so wet I decided that my thumb could do a good job of plugging that hole. The wetness was practically dripping onto the floor and the kneeling position with my legs spread wide, forced my lips open wide which made me even more randy. I doubled over and leaned my forehead on the floor, quietly moaning to myself with pleasure.

I took the thumb out of my pussy and stroked my clit from side to side with the soaking wet thumb. I momentarily stopped the rubbing to inserted a third and fourth finger in my ass. So tight. Such a strong and willful muscle. I consider that this felt so desperately good that if I make myself cum, I may cum so hard that I may be spent bursa escort for the rest of the night. I decided against it, so I can save myself for my lover. But I continue to stroke my clit….it throbed with desire, I could not stop.

I decided not to stop. I felt the hotness burning inside my femme parts…fingers in my ass, finger up my pussy, another stroking my clit. Within moments, I came…. and I came so hard that my stomach knots into an uncontrollable kink, paralyzing me from taking in air, which intensified my climax even more. I remained in this state for nearly a minute, as my orgasms typically last a minute or two or three. I released my stronghold on my clit and I rolled to my side in a heap, gasping for air and needing to stretch that kinked muscle in my abdomen. What an intense orgasm. I felt guilty, but luckily that night my lover was grumpy, tired and preoccupied with work and wasn’t interested in sex. Lucky break for me.

Session — My man had half jokingly quizzed me a few days ago about my afternoon showers. While it’s not unusual for me to take them, their frequency may have increased since my “yoga” stretching has started. Today was a cold day, I got home and hopped in the shower to warm up before I realized I hadn’t done my ass stretching. I only remained in the shower about 5 minutes, dried off and kept my pink, warm fuzzy robe around me for warmth. I didn’t know if the warm shower helped or if things are just stretching well, but I reached a new level today.

I laid across the bed sideways and pulled my knees up to my face, exposing my freshly showered girl parts. My pale feet naturally rested on the wall at the head of the bed. I had oiled up 2 fingers on both hands—not knowing how much I could take. As before, the first and second of the right hand easily slipped into my ass. As I had noted before, having both hands down there can be a difficult feat, so I decided to see if I could get my ring finger of the same hand in. It did, though noting I need to cut finger nails again.

The three fingers in my ass, forming a sort of a triangle. I knew my lover’s member is much larger than my little triangle, but all will be well with time. This passage is so tight—he is going to love this. In this position, a second hand might have been too difficult, so I decided to add my thumb! The thumb slid in after being lubed properly. I tried to open them and my ass absolutely would not allow it. I continued with the clenching and releasing exercises and with my other hand, stroked my clit from side to side.

My thoughts drifted to wondering why my lover has never stroked me this way…I suppose the natural thought is to go along the folds of the lips up and down, but this way feels divine! With my knees near my ears, I stroked my clit slowly and methodically…I softly groaned to myself. Then I used my left hand to insert two fingers into the middle of the right handed triangle. They easily went in, but it was tight—very, very tight—and I used them to spread the others apart, as tiny of progress as was possible, I held that for a few minutes.

I decided that my man most certainly will want to do some stroking himself when he has me in this position. And by that, I mean in and out of this tight little ass of mine. I decided to try a little in and out action without completely pulling out. It was fine…actually felt –possibly– a little good, and I continued to stroke my clit. I wanted to cum so badly, but I knew that today I would be saving that orgasm for my lover.

Every stroke of my clit made my ass muscles clench a little—if my lover even lasted five minutes in my tight ass, I would be surprised. I saved my orgasm, showered, and donned some purple Jack skellington over-the-knee socks, a thin, tight white shirt, skipped the panties, and hoped to ravage him when he got home. I sat in bed with my book and waited for my lover.


Today is Friday and I have worker men in my house replacing the old heating system. They have no idea what I’m doing upstairs in my bedroom. Today, I decided I was going to see how far I could take my “yoga.” I lubed up all five fingers on both hands (just in case) and then in an afterthought, decided to lube up my purple vibrator as well. I started with one and then two fingers and again, my little asshole still seemed impossibly tight. After about 5 minutes, my two fingers were practically numb. I worked the fingers around, side to side, front and back…my clit pulsated with expectation.

I decided I could probably handle my sleek purple vibrator, which probably isn’t much wider than 3-4 small fingers put together. I know my man is much thicker than it, but things are “cuming” along. I inserted the vibe slowly—it fills the impossibly small ass cavity and I feel full, but my pussy is so empty—a very new sensation.

I rolled onto the floor on my knees again, forehead on the floor, knees apart. I had a hand towel and wondered if my lover has been noticing how many rags and towels I’ve been going through. I used the towel around the base of the vibe to prop it upright and sit up on my heels, with the vibrator jammed into my little bursa escort bayan space. I played with my clit until my pussy was dripping wet with pussy juices and decided to see if my little ass could handle some movement. I slowly raised up and down on the stationary, propped up dildo…still stroking my wanting clit. I bobbed up and down on the dildo, this time in a slow rhythm… I became proud of myself because today I was ass-fucking my vibrator! My lover is going to be so surprised!

He had a conversation with me lately about not telling each other things right away, and I hope he doesn’t get mad at me about this, but I wanted to see if I could even do it first (so I didn’t disappoint him if I couldn’t). And second, I wanted to give this to him as a sort of gift. A surprise gift. I hope he loves it. My mind wandered off wondering if he will end up liking my ass more than my pussy—it is afterall, far tighter than my pussy! I ponder this question for a while.

As I returned to the task at hand, I again wanted so badly to cum…it wouldn’t have taken even one more stroke of my clit to send me over the edge, but I decide to save myself for my Lover. We took a walk that night and worked out a spat we had had and by Saturday morning I was so incredibly horny that within minutes of him fingering my wanton pussy, I came so hard I almost passed out. The day was filled with teasing, tasting, licking and screwing—he even ate my pussy in his car sitting in the parking lot of the grocery store! I love my man. One moment while he was licking my pussy in the bedroom, he licked it side to side! OMfsm—has he been reading my chronicles?! This put me completely over the top within a minute! Sunday morning was good as well….but Sunday night, oh, Sunday night! My kinky man emailed me a video of something new and fun he wanted to do, which, in part, involved ass-training on him! Imagine my delight to get to show of some of my newly learned skills in training HIS tight ass! Won’t he be surprised when he finds out what I’ve been up to!

Session—next. I met a woman today—when I left the business meeting, I immediately texted my lover that I was hot for this woman. I think he got a little turned on by the message… He and I have been talking a lot lately about strap-ons and double-sided strap-ons. Now another woman to fantasize about…I’m not getting much work done today. It’s been 2 days (all weekend) since my last “special yoga” session.

This time I go straight for the purple dildo. I insert one one finger first to guide the vibe in, slide the finger out, and push the dildo as far as I can. I have measured my vibrator—it is 6 ½ inches tip to end (6″ plus the base where the batteries screw in). I have only gotten it comfortable in about 3-3 ½ inches. My man measures a full six

+ inches. Still lots of work to do. I relaxed a few moments to let my body adjust to its thickness. I attempted my clinching exercises but my little asshole feels so full. As I jiggled it a little in and out it started to feel good elsewhere. As I knelt, I propped this mechanical shaft between my toes and began to stroke my clit. The tightening of my little asshole tried to push out the sleek vibe.

I thrust probing fingers into my pussy and realized how incredibly wet it is and draw some of those pussy fluids out onto my eager clit. The anal stimulation does not seem to gratify me by itself, but paired with the other simulations it causes a wonderful combination of sensations. My mind wanders to the woman I met today…wondering if she and her husband have ever done anything like this. Wondering also, if she has ever had a female lover outside of her marriage. I could not tell if she is just friendly or if she felt the electricity like I did today—I turned on my vibrator while it remained secure in my tight little ass. Fast forward to the evening…I did a second ass training on my man. Hopefully mine will be “ready” before his is!

Next session—I only had a short amount of time before he got home, so I went straight for the purple vibe. I pulled open my little hole with my finger and slid the oily vibe directly in. It went in with ease and I decided that next time I will be ready for a larger size.

Next session—This day, I found an old, sleek, jelly-like anal plug in my “toolbox.” It was slightly smaller in circumference than my hard purple vibe, but I figured since I had a time constraint, I could lube it up, insert it, and attend to my day. In the meantime, I looked up what others are saying about how deep one can penetrate the ass and prepared some literature for my lover. I’ve decided that since I will have company in the house for the next 12 days, I will stop by the “toy store” on the way to the airport and pick out some butt plugs that are increasing in size. By the time my company leaves, I might be almost ready! I hope my lover will be pleased.

Next session—I stopped by the toy store today. I bought a 2-pc kit of two jelly-like ass-trainer plugs. One is about the size of a plug I have now, but I will give it to my lover. The other is the next size bigger—I think I can start with that one. They are in a graduated-bubble-like escort bursa shape. The top is a small bubble and the bubbles get larger toward the base. The longer one is probably a full 5″ long. Additionally, I bought one more size up from that. I call it the “big black bubble butt” haha. It too is the graduating bubble shape, but really fat (and not as long).

When I got home I lubed up the middle size five-incher. It seemed almost impossible getting it into my small hole, and took about 5 minutes…BUT it didn’t hurt and I got it in. All 5 inches. I wore it around the house under my clothes for a few hours. I will send my literature to my lover tonight. I will also need to tell him that we will need to use a condom based on some of the info I found. I can’t wait to deliver my surprise to him.

Next session—Again the 5-incher. Actually, I think it may be 6, but unsure. It only took about a minute to get it all the way in today. The part closest to the base is the fattest part—it might be fairly close to the circumference of my lover. My tight ass isn’t ready yet. I want to be fully able to accommodate him with no pain—and maybe even….pleasure. I sat today with the 5-incher ass trainer in my little hole for about an hour. The longer time wore on, the hornier I became. My man was supposed to be home early today—I do hope he hurries up, Angel is randy. I thought to myself, “Maybe I’ll just use the vibrator for a few short moments until her gets here.” A few minutes inded.

Next sessions (Oct 4th–5th + 6th)—It was the weekend + and I didn’t want my man to know what I was up to, so I didn’t take up the trainer I bought. However, I slipped one of my tiny older butt plugs in my ass before we had a planned “rough” sex session. Well, probably not really rough by porn standards, but he fucked me hard. On all fours in the family room and then on the stairs. He fucked me so hard the plug popped right out of me!

The next day there were promises of face sitting—so while my lover played video games with our company, I sat upstairs with my new 5-incher shoved in my ass. Having it there made me good and randy, and eager for the face-sitting later in the evening. I stealthily removed it before he knew anything. Monday I had plenty of time to train my little ass. This 5-incher plug is proving to be a bit of a challenge—it has 5 bubbles, the tip being the smallest, and the 5th at the base being larger and out of proportion (thicker and longer) near the base. It is still difficult it get it in and out over that 5th fat bubble. I’m going to slyly measure the circumference of my lover’s manhood tonight with my hand. I’d like to see how much bigger he is than this trainer plug. I hope I’m getting close to being able to handle his fat cock, but I know it is going to be at least another week or two. I took a few pictures and will send them to him when the time is right.

Session next—My lover and I had been having a little grumpiness between us the last few days. I won’t stop my ass training though because I am doing this because I love him very much and despite feeling negative toward him temporarily, I know that he will be ecstatic the day he finds out I am ready for him to fuck me in the ass. I continue on because of my love for him.

I have been a little frustrated because it seems like I haven’t been able to move up from the 5-bubble-5 incher. I had limited time this day and was just going to keep the plug in my little ass for about a half hour while my man was driving home. I was frustrated with my stall in progress and knew I probably wasn’t going to get laid that night either and decided to see what I could do to speed up this process.

I went into my bathroom and knelt on the floor. I pulled the plug out only part of the way, just enough so that the fattest part of the 5th bubble was expanding the tightest part of my opening. I was angry. Angry at my lack of progress, angry at my lover, angry that I haven’t been laid in four days, angry at the internet, angry at the world. I kept it there and angrily took to doing my squeezing exercises. I was determined to get past this fat bubble this week!

I put my hand mirror under my ass to see what I was doing and decided that I was going to fuck my ass with the fattest part of this dildo and get this show on the road. I fucked myself with it for several minutes with no issues and decided that next time—next time–I’m going for the Big Black Bubble Butt (BBBB) that I bought. I’m going to get that fat plug in my ass even if it kills me.

Next session—This evening, I broke out the BBBB. It mused that it looks like a chess piece. It is about half as long as 5-incher, and has only three bubbles—but they are FAT. After lubing up, the first and second bubble went in somewhat easily, but the third bubble just wouldn’t budge! I tried on my knees, using a mirror, but I could not even force it over the third bubble. I tried for about ten minutes and gave in to failure. I realized however, that this second bubble is about the same size as the largest part of the last plug, so at least I have that. Giving in to the failure, I donned a tightly fitting thong to hold it in, and went about my evening. My lover had better fuck me tonight, or I’m going to have to deal with it myself. I haven’t even held his cock in my hand in five days! I have become very grumpy in this state.

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