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Nis 9, 2021 // By:analsex // No Comment

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Given the semi-vast extent of my sexual experience people are often shocked to learn that for quite some time I remained an anal virgin. Then in the fall of 2003 when I started college I met Tom Friedlander who was on the swim team and was the first boy to whom I got engaged.

I need to clarify something here. As I say, I started college in the fall of 2003. Later on I speak of finishing my first year in college in 2004 at age eighteen. Like the vast majority of people in the USA you start a year in the fall and finish next spring, almost always in May. That is what I did. I then say I got engaged a month later on my birthday. So I would have turned nineteen a month after finishing my first year of college in the Spring of 2004 when I was eighteen. Therefore one can figure I finished my last year of high school in the Spring of 2003 when I was seventeen and turned eighteen a month after that. Therefore when I met Tom in the fall of 2003 I was already eighteen.

It probably would have been easier to say I was born on June 21, 1985.

Anyway, Tom and I hit it right off. No doubt Tom was first attracted to my puppy brown post-summer body. I know because when he kissed me, he in those little swim suits the boys wear and me with the front of my tank suit pulled down, I could feel his boner against my leg almost like it was in me. And two Saturdays later it was. In me, I mean. The regular way, of course, in my vagina, because at the time that’s the only way I did it.

Anyway our relationship progressed swimmingly and we spent lots of time together doing all sorts of things including making love, me on top, me on the bottom, me tied to the bed, me dressed as a French maid (okay, I made that up) cowgirl and reverse cowgirl. I did everything he asked me to do (well, within reason). But I wouldn’t let him do me in the bum. It wasn’t personal, after all he was very good to my bum, admiring it, patting it, putting lotion on it. But I wouldn’t let him stick his dick in it. Then we decided we’d get engaged and I knew if we were getting married I had to. Let him stick his dick in it I mean. At least after I got my ring.

We decided we’d get engaged on my birthday in June so I had time to plan things out. By June my body was always white as snow. I purposely stayed out of the sun all year long except for the summer to encourage my body to become white as snow because that’s the way my photographer Harry and the members of The Little Sketching Group wanted me and after all they paid me to get naked so they did have certain rights. Each year a number of boys would also see me naked but once I took my clothes off none of them really cared whether I was white or brown. Anyway, the thought of Tom sticking his dick in my soft white bottom filled me with apprehension.

Fortunately I have female friends who had faced the same situation, or something close to it, and emerged smiling, if indeed they walked a little funny. I immediately went to see Kristie. She worked and lived on the Harrington’s estate next door to our house training their horses. She also functioned as a kind of majordomo for The Wenches whereas she had access to various facilities we needed to carry out our activities. Going back to the days when she had started working there mucking stalls part time she had maintained a personal relationship with Jonathan Harrington whose family owned the estate. And going back to the days when she had started working there, Jonathan had been doing her in the bum. And she could still ride a horse so that was encouraging.

Anyway Kristie understood my dilemma and proved of infinite help. She had had scant time herself to prepare for the pleasures of anal love making given Jonathan’s insistence and not having had the support of The Wenches who didn’t organize till later. But she had helped my friend Claudia and also Brittany who was the first of us to marry. Brittany wanted to learn about bum fucking in order to please her prospective husband. Who Claudia wanted to please must remain a topic of speculation.

At any rate Kristie discussed her experiences and imparted to me much wisdom on the subject. It might be pushing things to say she enjoyed taking it up the ass but she acquiesced and I figured that with preparation I could too. And Tom had kind of a small penis which I figured in this case was a plus, though in other respects it might not be. Jonathan had a small dick too. I know, he has shown it to me on several occasions. I never got any information on Brittany’s husband’s assets but she smiles a lot.

Anyway, secure in the knowledge that Kristie would help me I went to see Brittany. Kristie had implemented a program for her, facilitated by The Wenches, which prepared her nicely to accommodate her new husband’s desires, as well as his penis, with no ill effects. On a number of successive visits to Kristie’s she expanded the ability of her rectum to accommodate objects of gradually increasing girth and length and of her mind to accept the idea that her rectum should be thus employed. canlı bahis

In the relative privacy of an upstairs room in Kristie’s house Britt would strip completely naked (this was a Wench project, after all), have her wrists bound tightly behind her (Wenches) and be tied even more tightly (common sense) bent over a table. Then, with Brittany unable to resist, over a period of days, Britt having been generously lubed, Kristie would gently insert objects of increasing size into the critical orifice while interested parties watched. Brittany would do her best to relax and breathe deeply, kind of like she did in yoga, which she enjoyed. Happily, everything worked out fine, and Britt now also happily takes it in the ass when ever asked (by her husband) and enjoys it.

So we were set. We began my conditioning program at the end of my first year in college, 2004, with me still a daisy fresh girl of eighteen. We had a month until my birthday upon which I was to get my ring and thus presumably begin to enjoy the pleasures of anal love. Each session proceeded about the same. I would show up at Kristie’s and repair to an upstairs room. There I would find Kristie, Brittany and whatever spectators cared to appear. This being a Wench activity, spectators who were boys had to pay. I would strip bareass naked and Brittany would tie my wrists behind my back, my hair in a ponytail, blindfold me, stuff my panties in my mouth and secure them with a length of rope.

I would lean over a table designed for a lamp but customarily used for spankings. It was about two feet wide and two feet in length and was bolted to the floor in case the object of the exercise struggled. The table top was thankfully padded so my boobs, such as they were, would lie in relative comfort. Britt would tie me firmly to the table, and I do mean firmly. I could not move my upper body. Then she would tie each of my ankles and my legs, just above the knees, to the table legs. Now I couldn’t move at all and my lily white bottom was perfectly positioned for what was to be done.

First time I went was relatively easy. I washed myself before hand and wore just a short dress, panties and my running shoes. There were four paying spectators, all of whom I knew and all of whom had seen me naked before but not for at least a year. Having completed my first year of a university swimming program I flatter myself I was looking fine. I was white as a sheet except for my nipples and both sets of lips. I was shaved bald as a cue ball. My tummy was flat as a board, my bum and my thighs suitably firm. My boobs were, well, my boobs. I pulled my dress over my head, untied and removed my running shoes and slipped off my panties, leaving them on the table to facilitate their soon to be placement in my mouth.

Brittany started doing her bit. She used hemp, I think just to tweak me, the roughness just barely irritating against my skin. I crossed my wrists behind me and she tied them tightly together. It hurt. Then she tied my elbows together too, an easy feat with a swimmer. That hurt. Then a rope around my belly to secure my hands to my body which didn’t really hurt and another rope around my body just under my boobs to secure my arms. That DID hurt. She left my hair in the ponytail it had arrived in and blindfolded me with our standard black cloth.


She stuck my folded up panties in my mouth and I obediently left them there while she rigged a rope through my mouth and around the back of my head to hold the panties in there. They were tasteless but the hemp hurt my mouth at the corners.

With me now sightless she pushed me up to the table and bent me over it. She passed one rope between my arms and body at my armpits and another over my back at the level of my bellybutton and tied each tightly under the table. Then she cinched each rope tighter still with another rope passed under me and pulling the first two ropes tighter to my body. I couldn’t move anything above my by now thoroughly wet pink twat. It hurt but my body purred nicely. I didn’t even think about what Kristie was going to do to me. Britt finished tieing my ankles and then my knees to the table and we were ready for the next part. Bent over as I was, my asshole and my hot wet pussy lips must have presented the boys a welcome view. Well, they HAD paid.

Kristie stepped to the plate, as it were. I couldn’t see but presumably she had donned a glove and had opened a tube of lube.

“Now just relax.” Sure. I felt her finger at my bum hole, cool with the lube, gently just kind of stroking outside of me, once, twice, maybe six times, an upstroke, then removing her finger, then another and another.

“Okay, relax.” Then softly she inserted just the first joint of one finger into me. I cringed just a bit when I felt her enter me just the way I cringed a bit the first time a boy put his dick into my girlhood four years earlier. I could hardly move but I could kind of roll my hips a tad and I did. I couldn’t talk but I could take a breath. She did it again and then bahis siteleri again and again just sticking her finger in there.

“Okay.” Then a little further, just a bit more finger up me and I tried to resist and I tried to protest but I couldn’t much and she didn’t stop and then a little more and after a few minutes she had her whole middle finger up me and every so often she stopped for more lube and I knew it meant it would go up me a little further when she put it back in me and it did and then her whole middle finger was in me, slippery as could be and it didn’t really hurt but it felt really weird and I can’t really describe it.

“Okay?” This time it was a question and I tried to murmur okay and in any case she took her finger out of me and gave me a minute. And when my minute was up she put her finger back in me and when she got it in there she began to turn it slightly and I quivered again and now I could really feel it strangely inside of me and it wasn’t really unpleasant just weird and she kept turning her finger one way then the other for what seemed like ages but probably was only two minutes and finally she took it out.

We waited a few minutes and Britt stroked the back of my neck gently and I felt hot both temperature wise and sex wise knowing something was being done to me sexually though it was new and knowing I couldn’t do anything to prevent it and I could hear the boys giggle like girls no doubt staring at my asshole but I couldn’t prevent that either.

“Okay.” This time it was a statement and I could feel Kristie at my bum again and feel the coolness of the lube and feel her at my bum hole and slowly entering me again only this time it was wider. This time it was two fingers and this time I could feel myself being spread more than maybe it hurt and I tried to move but I could only roll my hips but she pressed a little harder and she was in me this time with the two fingers. She moved them in and out maybe just halfway and then in and out some more and then further in and out and I was beginning to get a bit of a feeling of being fucked in the ass.

How much wider is a guy’s dick than two of a girl’s fingers? Maybe some but it’s only wide in one direction and it felt really uncomfortable but good at the same time and finally her fingers were all the way in me and going in and out and then she’d take them out and put them back in. I started to move my hips a bit like I was on top of a guy and I could actually maybe see how you could cum that way and she kept doing it and kept doing it and by the time she stopped I swear I was halfway there.

So we stopped again and I was breathing kind of hard and Kristie laughed and told me “Good for you!” and they left me there and just let me relax which is what she had been telling me all along and then Kristie said that was enough and Brittany began to untie me. It took five minutes to get the rope off me and as she took it off it reminded me how tight she had done it and how much it had hurt but we were Wenches so I just said “Bitch!” to myself and figured I’d have a chance to get back at her some time. The boys were still there so I just stood there stark naked and let them look at me because after all they did pay for it.

Kristie brought out the hardware we’d be using in subsequent sessions. The Wenches had all sorts of cool stuff. There were these butt plugs that looked for all the world like little Christmas trees, maybe skinny ones, of gradually increasing sizes. Butt plugs, of course, can be left in you but the idea for us was just to get something thicker and longer into me over a period of time until I was ready to receive a guy’s dick. I think I mentioned that the dick in question was not all that large so that helped though I would have preferred it were bigger when we did the deed in a more conventional fashion.

Beside the Christmas trees there were similar things that were wider which Kristie said I would need to be able to accommodate. These had handles on the end, like rings, so I guess they couldn’t get stuck in there. Then there were longer ones that were ribbed and that looked more like penises except penises aren’t ribbed but I’d need to be able to take the increased length. Finally there were things that were shaped like dicks with heads on them just like a guy. These were still longer and of a good thickness and that was the final exam, if I could take the longest and fattest of those I would be ready. So that was it for the day, we knew what we had to do. Kristie said plenty of lube and I’d do just fine. We were done so I got dressed and as soon as I wasn’t naked anymore the boys left and I walked out with Britt.

So two days later we went at it again. This time Jonathan Harrington came, which was a surprise to no one. He knew someone would be naked and probably hoped for Brittany but got me. The routine was the same as before except we skipped the blindfold and they gave me a bit to wear in my mouth, after all it’s a horse farm. Britt tied me just as tight as before, the bitch, but bahis şirketleri it was probably good I couldn’t move. This time Kristie used the butt plugs that looked like Christmas trees. She started with the smallest one, well lubed and I could feel the coolness of the lube on my asshole and then the point of it going in and then she was pushing it and it got wider as she pushed and I could feel it and there was just a bit of a stretching feeling and then it was in me and she just left it sitting there inside me for a few minutes. Then slowly she started pulling it out and it didn’t really come out as easy as I thought because I kind of closed in on it and I squirmed and kind of shook my head.



A few minutes later she started with the second one. The coolness of the lube and the point at my asshole and her pushing and even though there was plenty of lube I could feel a stretching but it didn’t really hurt it just felt uncomfortable and it took a bit but finally it was in there and in a weird way it felt good. Time to come out and again it was a bit hard and my body seemed to want to keep it in there and I squirmed and finally it was out.

Third one wasn’t much different except it was wider but it never really hurt and when she got it out after its five minutes in me I felt good. We talked for a minute with me still tied there and she suggested I wear the small plug home and I said okay so she re-inserted it. Then the same routine as last time, Britt untied me and I stood there naked, especially since Jonathan was there, just tempting him, hoping he’d get turned on and stay after and fuck Kristie’s brains out. Then I got dressed and the other guys left because I wasn’t naked anymore and then Britt and I left. I don’t know if he fucked her, but her brains were still intact next time we went over.

I wore the butt plug home and ate dinner with it in me with my Dad sitting next to me and he asked me what was new but I didn’t think I should tell him I had this thing up my ass. Later I told my sisters but I never told them it was part of my training to let Tom do me in the bum. I took it out before I went to bed but wore it around the house the next two days till we went back to Kristie’s.

We did two more sessions, first with the dildos with the ribs and lastly the longer ones that looked like real dicks. Kristie did a real good job, plenty of lube. I was going to insist Tom do the same. Just because I let him tie to the bed face down didn’t mean I wasn’t going to get my way. Kristie always put the things in gently, another thing I’d insist on. I tried to concentrate on relaxing, breathing and bearing down to get it in there. The first dildo session was just to see how far I could get it in me. There was no pain but it was uncomfortable and I never really felt like I could get off doing it. Even when Kristie started moving it in and out I couldn’t really get that turned on.

In our last session with the dildos that looked like real dicks we wanted to try to get them all the way in and I did for the first two but not the third and longest one but no matter it was two inches longer than Tom. Best thing was Kristie started getting up a head of steam with faster and faster strokes and it felt good and introduced the possibility that if I could get relaxed and concentrate on my feelings I might be able to come but maybe not.

When I was untied after the last session the three of us talked about how to do this with a guy. After all the two of them had plenty of experience with real guys and were happy. Lube you needed, of course, and going gently. It sounds trite but the girl needs communication with her partner. You need to talk about it before and during. No slam, bam, thank you ma’am stuff. Before you get penetrated you need to make it clear what you like and you need to get comfortable and turned on. I thanked them, they wished me luck and Britt and I headed home.

So my birthday came and I got my ring and we had an engagement bash and next day he and I headed up to Bar Harbor. Because of the occasion we stayed at the Bluenose which is viciously expensive. I looked at the four poster in our room and knew what was going to go down on it. We spent the day at Sand Beach because it was warm for there for mid-June. I wore my littlest bikini so he’d be really horny. We ate dinner afterward at Rose Eden and went back to the Bluenose. He had me strip for him, tied me to the bed on my back and did me the regular way. I wanted that because I knew he’d be softer second time around.

When he was done fucking me as God intended he got off me and left me tied there so he could get it back up. We talked about how I wanted it done. We had lube and he promised to use it and I told him to go slow and gentle. He came back to the bed and untied me and told me to turn over on my tummy. I spread my arms and legs out to the four corners and he tied my wrists to the headboard posts. He put a pillow under my hips to raise my ass up and tied my feet to the footboard posts. He did as I had asked and lubed my asshole liberally, gave himself a few quick strokes to get harder and lubed his dick. The softness of my bare bum stared helplessly up at him and he moved to take advantage the situation.

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