Two Firsts for Jill

It was my opinion, as I'm sure it is for most women my age that after you're in your forties the days of new sexual adventures are over. Other than maybe a new fantasy taken from a romance novel most of my sex life was in a rut. Don't get me wrong my husband is great and I knew he loved me but after so many years of married life, the thrill was gone. To make matters worse my vagina was so stretched from childbirth I could no longer even feel my Joe inside me. I also knew if I couldn't feel Joe, he couldn't feel me. We carried on with our usual bouts of sex not loveless, but joyless. It was the 'elephant in the room' we dared not talk about; I mean anything I said to Joe would sound like a slight to his manhood. Joe was too much a gentleman to say I was too big.

It all came to a head one night as I sat astride Joe silently wishing he would cum so I could go take a bath. I increased my tempo and whispered something in his ear like 'cum baby'. I finally realized he was tapping me on the shoulder,

"Honey can't you feel I fell out about ten strokes ago."

First, I was mortified and then I was mad and we ended in a big fight. We said some nasty things like him calling me the Kentucky Wonder Cave and me telling him he definitely wasn't a member of the Giant Redwood Forest. I went off to my bath and he went to sulk in front of the TV. As I lay in the tub feeling guilty for all I'd said, I realized we had finally brought up that elephant. Now that it was out in the open maybe, we could talk about it rationally.

I got out of the bath and went to find Joe to apologize for something that was all my fault. He turned off the TV when I came in the room, and bless him he apologized first. I told him I loved his cock and to prove it I bent down and gave him a blow job, which I hate, even swallowing his sperm, which I hate even worse. After, I crawled up in his lap and said I was sorry that I was so stretched out I couldn't feel him anymore. I told him I still wanted to have sex and I loved him more than ever but what could we do to increase his pleasure. He told me that now right after he had cum so much he couldn't think about and that we should talk later.

The next day I went on line looking at those sexual advice websites for women and after surfing for a while found something that perked my interest. A woman whose problem was similar to mine was told to try anal to give her husband some pleasure. This was something I had never even considered let alone tried. The more I thought about it the more the idea interested me. That night when Joe got home, we discussed it and he wanted to try it right away but I refused. I told him I lost my cherry to a boy in the back seat of his mother's car and if I was giving my other cherry to Joe, it was going to be a special occasion.

After school, Friday I shipped the kids to my mother's for the weekend. I came home and douched my back door, then took a long hot bubble bath. Joe and I had a romantic candle lit dinner and he was so sweet to bring me roses. I had candles in our bedroom and a new bottle of erotic lube. I was nervous and afraid of a painful evening. Joe saw this right away, was patient, and told me it was my call if I didn't feel like it we would stop. He started massaging my rectum with a lubed finger and as I began to feel comfortable with it, he increased it to two. I could tell by his breathing that Joe was almost beyond excited so I asked him to try his penis but to go slow. Once he got the head of his dick inside, my sphincter closed down in panic. I told Joe to stay just where he was, I remembered my breathing exercises from having babies. As I breathed as I did in delivery, I began to relax my back door and Joe just slipped in. I could not believe how full I felt and I made Joe hold still and then as I relaxed more I began to feel more at ease and Joe began a slow rhythm. Alas just as with my first cherry, the 'boy' didn't last very long and within about three strokes my Joe was filling my anus with his sperm.

OK, anal sex for Joe fantastic, anal sex for me, not so much. Yet I was happy for Joe at last my body was giving him some pleasure. Anal became a regular sex practice for us, Joe always asked, never expected but then I never refused either. Then one night after a little too much wine loosened my tongue I confessed to Joe that I got little pleasure from anal. I told him I liked doing it but I was one of those women who climaxed from vaginal intercourse and I felt I was missing out. We went back to our old way of making love but that just meant that both of us were not enjoying it.

Joe came home from work the next day and said he had an idea, he asked if I would listen with an open mind. Talk about off the wall; he was on the back of the job site peeing with his assistant Carry, when he happened to look down at his dick. Joe said,

"Honey his cock must be ten inches long and five inches around."

I said something about boys and their toys but he kept on going.

"No listen to me; he is the answer to our problems. If you'd fuck him I know you'll feel that monster inside you."

Well believe you me I threw a fit,

"Just what do you think I am, some kind of slut who sleeps around looking for that perfect cock? Besides he is just a boy, why do you think he'd want to sleep with an old woman?"

"Jill he is not just a boy he's almost twenty and he's really a good kid. Don't tell me you didn't notice him drooling over you at our barbecue last month. I telling you he would jump at the chance to have you. Jill honey, I don't think you're a slut; I just want you to have some pleasure."

What Joe didn't tell me until latter was he had a secret fantasy of watching me sleep with another man. The more Joe talked about it the more comfortable I became and Carry was cute in a high school quarterback sort of way. In the end we decided to invite him over for dinner with no mention of why and let nature take its course. While having cocktails before dinner, Joe asked me into the kitchen,

"Honey you're going to have to take the initiative here, poor Carry is in way over his head, I know he wants you but he is just too shy. Please I want this for you, you take the lead, and he will follow."

"What about you, what are you going to do?"

"After dinner, I'm going to play drunk and go off to bed to pass out for the night."

We all drank too much, I needed it to relax my nerves, I think Carry was so nervous he just drank to have something to do and as for my husband he wanted to make sure Carry thought he was drunk. During dessert, Joe slurred something like, you two have fun, gave me a kiss, and went to bed. I decided it was now or never I went over to Carry and just kissed him deeply with a lot of tongue. I could tell he was already excited by the way he was breathing. I felt just like a hussy and I decided if that's the way I felt then that's the way I would act. I grasped his dick and got the shock of my life, Joe was right he was huge. Without a word, I led him to our spare bedroom and as soon as I got my clothes off he lost his shyness and became an animal. I had almost forgotten how good it felt to be thoroughly fucked. It was all so wild I remember a thought ran through my head 'I hope his condom doesn't break' but I really didn't care I just wanted the feeling of my pussy being pounded. I must have cum five times before Carry filled that magnum rubber. I don't think Joe knew but Carry was not the first strange cock I had enjoyed since we had been married but it had been awhile and besides the size, I also enjoyed the excitement of it all.

Before Carry left, I told him I hoped we could do it again soon and he said anytime. After he left, I went to Joe with no idea what his mood would be. He was lying in our bed naked rubbing himself. Turns out he had been spying on us and was so aroused he could hardly keep himself from cumming on our hall rug. He took me from the rear and as he filled my anus, he said he wished Carry was deep in my pussy at the same time. Joe came almost as soon as he said that, and it got me wondering if I could handle both men at the same time. As we lay beside each other Joe asked me for a detailed account of my new lover and what all we did. I began telling him of my adventure and the more I said the harder Joe got. I casually asked what he thought about both him and Carry doing me at the same time. Joe moaned and told me he had just cum on his belly. I told Joe if this was what he wanted he would have to set it up and I was leaving it all up to him.

The next day Joe called me from work saying it was a go and both he and Carry wanted to try it that night. That left me with a lot to do and I started my day at the drugstore buying condoms. I must say I enjoyed the look of shock on the cashier's face as I laid a whole box of magnum size rubbers on the counter. I went home, douched both holes, and then took a long hot bath. That was the night I found sexual nirvana as I sat astride Carry taking his cock deep inside me I had my first orgasm. When I felt Joe, pushing through my rectum is when I realized I was now fucking two men at the same time and just that thought brought on my second orgasm. You could almost feel the excitement in the air and the smell of sex was everywhere. I knew neither man would last long nor I but I wanted to get as many climaxes as I could. I felt like a sexual princess satisfying two men at the same time and as I felt Joe empty inside me, I felt Carry's balls tense and release. This brought on one more orgasm for me, how many I had I don't know as I lost count.

This was just the first of many nights with my two he-men and they only got better as we became more skilled with our lovemaking. Then one night after Joe and I had said good night to Carry I said,

"Joe what do you think about me inviting my friend Sharon over and see if you can please both of us?"

Well that tale will have to wait for another story.