Book 2 Teri

It was about a year after Jill and I broke up that I met Teri at a party, she was a divorcee around ten years my senior. I was in the best shape of my life and had remained celibate all the while. The fact that she was so much older would not be an issue if things didn’t get serious. As to her physical appearance she was not what I’d call pretty but she was not ugly either, though she did look her age. As to her body, when I finally got to see her naked, I was pleasantly surprised. Where I had expected droopy breasts, a saggy ass and a road map of veins and wrinkles, she had small but very pert boobs, smooth skin, a flat belly and a small tight ass that was only a touch boyish. The only thing that I didn’t find all that attractive was her child bearing hips, they didn’t look great on such a slender woman. During the sex phase of our second date, she kept her small ass firmly planted on the mattress, she wouldn’t even let me put my hand under her to feel it. Now being a died in the wool ass man, I determined to get to the bottom of why (pun intended) and fix it so that we could both enjoy a fuller sex life.

The next day rather than a happy go lucky date I took Teri to a quiet place where we could have drinks and dinner without having to run all over the place. After Sid, the owner, chided me for not coming around enough for his liking he gave me a warm hug and left us to our devices, I gently probed the older woman indirectly for why she was so anxious during sex. Now bear in mind that I was only 27 at the time with only my marriage to Jill as a frame of reference and that was mostly sex and booze and fun until she left me suddenly. I had no idea what would happen when a woman pushing forty would open up. I instantly regretted probing her. She began to gush with everything her ex-husband of 12 years had done. After hours of babbling, I finally got the nugget that explained why there was a broom stick up her ass. From what I understood, her hubby got tired of the same old thing after 11 years of marriage and he did not cheat on her. Instead, he wanted anal sex, she tried but from what I gathered he was not a man of any great knowledge or experience in bed and as such he hurt her. She pulled away from him and refused to ever let him do that again. As I said, he had no real knowledge, so instead of backing off and revisiting the situation when she felt better, he tossed her over and when she was face down he raped her up the ass, tearing her in the process. She screamed that he was hurting her to which he answered, “no I’m not” and callously continuing to rape her anally until he flooded her colin with cum. For months he would continue doing that to her until Teri stopped sleeping with him and would not let him anywhere around her. He met another woman and started to cheat on his wife and that led to their divorce soon after.

No kidding she wouldn’t shut up about her ex the whole evening and all through the drive to her place. Eventually I got her quiet enough to say goodnight, but I knew how to get her out of her funk, at least sexually. Her pussy was as tight as I have ever used, I could not believe how much trouble I had penetrating her. I had three virgins in my life and not one was as tight as Teri that had been married for 12 years. She was tough as nails though and never complained except for the first time when she asked me not to knock her up. True, that was an anti climax but I took ever caution not to cum in her. That issue was soon put to bed when she saw a gyno and got on birth control within two weeks. As careful as we were being, we both knew that an accidental pregnancy was waiting to happen. Eventually she relaxed with me enough to be more permissive with her body and after getting her used to fucking side saddle from behind then it was time. I knew what I was doing and was able to easily penetrate almost any woman’s asshole painlessly. After prepping her ass, I entered her and we both had a screaming orgasm after which she turned to me and asked, “how did you do that? Can you always do that?” I smiled tiredly and assured her that indeed I could. Things went on like this for about three months and then she started talking about wanting to play the field. Honestly, I was thinking about moving on anyway and wished her all the best. Suddenly her tone changed, and she told me that she was just mussing and wasn’t serious and asked me to stay. I was in no rush, so I agreed to stay without conditions.

Well, it came up again and again in the ensuing weeks, so I sat her down and told her how I felt. I was not interested in being with someone that continually nudged and unsettled me. If she wanted out she could go, I wasn’t stopping her. I told her that she was right and we were not married so we could both play the field but in my time when I put myself out there it was never longer than one day before some gal would grab me but if she could keep me was unlikely. I wasn’t looking for anything serious for several years and decided not to settle down again until I was at least 35 years old. Teri got her panties in a bunch and demanded I stopped bragging and get to the point. So, I did, I told her that in all likelihood that I would not have time for her once I started dating again. She was really put out by this and snapped; I don’t need your details. Once she calmed down, she said I really want to experience what the world has to offer, I was a virgin when I married my husband. It’s so good with you though that I want you to stay. I sat back on her sofa and said, if I’m hearing you right, you want to have sex with other people and hang on to me, does that sound about right? She had a look on her face like a deer in the headlights. Yes, she croaked visibly embarrassed and blushing. OK, I understand I replied reassuringly. She calmed down and looked at me attentively. There is only one way that a relationship like that can survive. Have you ever heard of swinging? Yes, I lived in the northern states they’re all over the place. Well, that’s what we’d have to do in order to remain a couple as you explore the things you want to explore. She asked me to explain the lifestyle and I did. I explained about open couples that allow dating with people outside the relationship, couple swapping, dogging, adult theater free use, gang bangs, 3sums, orgies and adult parties. When I was done she looked stunned but asked me how I knew so much. I explained that she was not the only woman on earth that was sexually repressed and wanted freedom from societal norms yet wanted to maintain their existing relationships. Can we do that? She asked haltingly. I said we could try but wanted to know what segments of the lifestyle she wanted to try, she replied, all. I then laid down my ground rules. As she pointed out we were not married so if she got pregnant she was on her own. VD was always a risk and I expected her do deal with any infections with the same grace I would. Jealousy and judgement was off the table for both of us. And finally, if either of us fell in love with another we should be honest and gentle with the other. She winced visibly at the last rule but it was the most important rule of them all.

And our journey began.