The Afternoons of Ann Ch. 07

Pick up where I left off. Tommy had been calling, after the three-way with Chris and D-P in the shower. He was struggling with the true nature of our relationship, and I can't say I blame him. All he knew about women from his point of view was dry-humping girls at high school dances, and make out sessions in cars. Suddenly he's dealing with the wants, needs and desires of a fully mature woman.

A fully mature woman who also happens to be a female pervert, that is.

Yesterday I was discussing my penchant for 'D-P' -- dual penetration (just in case you've been living under a rock for the past twenty years or you just emerged from a coma). As I mentioned, I've experienced this aspect of sex in the past and enjoyed it. Best. Sex. Ever.

But since I married my second husband I've only had it with a dildo and my husband, or with two dildos. My husband always seemed to enjoy watching that, and that should have told me something about his kink (that I have only now become aware of). Now that my husband and I are entering into a new and exciting openness in our marriage, it is my desire to experience it again.

As I mentioned earlier, we have this little role-playing game in bed where Dan has me calling him by his golf buddy's or business colleagues' names during our lovemaking. I do it to please him and it certainly pleases him. Then there was the episode, the sex party where we left early. That night we did the role-playing game and Dan had me calling him by our hostess's husband's name. Dan loved me harder and more fervently that night than ever before; it was obvious he had a thing about me doing it with another man.

Afterward -- in the afterglow -- we discussed it. Dan was very interested: if given the chance, would I do it with another man? He was pushing a little too hard for direct answers but I managed to field them with non-committal answers. There were a lot of maybes, I don't knows, depends on the situation, and other answers like that. I wasn't willing to go too far with it; I didn't want to possibly jeopardize what I have going with my husband.

The next morning, Dan was right back on the same subject. His persistence was actually getting annoying. Out of frustration, I asked "What do you want me to do just go out and have an affair, have sex with other men?"

His answer surprised me. He said "No, I want to watch." Then he went on to tell me about how exciting it would be to see me doing something with another man.

Dan is actually more interested in watching then participating. That to me is weird but I didn't tell him that. I was honest enough to tell him that it would be really strange doing something like that with him watching. Of course the whole concept intrigued me, turned me on even, but I didn't tell my husband that.

It quite surprised me when I first became aware of this side of my husband's sexuality. We're a conservative couple -- believe it or not -- he's a respected member of the local business community, active in Republican politics, I'm a high school math teacher. I've got a past, of course, but up until recently I'd resigned myself to a vanilla-flavored relationship for the rest of my life. I do love my husband and I've had my kicks, so this was tolerable.

Now it turns out that my husband seems to be turned on by the concept of watching me have sex with another man. I think I'd be able to handle seeing him with another girl, this is totally plausible, but surprisingly he's really not expressed a great deal of desire to go in this direction.

Personally I've never been a jealous person, so I'm pleased to learn my husband doesn't have a problem with the idea of me being with someone else. In fact, that's his kink.

Ever since the party he hardly talked about anything else. I could tell this was something he really wanted. Finally, I told him that it would feel weird having sex with another man with him just watching. I explained that it might be different if he participated but I couldn't just put on a sex show.

Dan responded, "Would it feel weird for you to give another man a blow job, with me sitting right there watching?" I told him I could probably do that and even admitted that might be fun under the right circumstances. He knows I enjoy giving blowjobs.

Of course, my good girl image is totally a factor. Dan has mentioned several times about being completely surprised that I would consent to anything like that happening. Actually, my good girl school teacher image was a major factor in all of this. A large part of the turn on for Dan -- his kink - is for me breaking that image, especially with my former students.

Its time long overdue to live out this fantasy of both of ours; me doing it with another man, in front of Dan.

And so I initiated the thing with Tommy. Up until now, Tommy had no awareness about my husband's part in it. He knows I want group sex -- more of the thing with Chris and him -- and he knows his part in arranging this. But up until now Tommy had no idea about my husband's kind; for me to have sex with other men in front of him.

Dan and I had decided that we were ready to take it to the next level. We decided to have Tommy come over, he and Dan would hang out in the Man Cave, down in our finished basement, watch football and have a few beers. Then I'd come down and the fun would really begin.

Fast forward to Sunday. I spoke on the phone with Tommy, in the kitchen. Dan was in the basement watching football. Two different levels of the house. "Hello Tommy."

"Hello Mrs. Morrison."

I think it's cute when he calls me Mrs. Morrison -- like from the days when I was his high school math teacher. Normally I tell him to call me Ann but I thought perhaps his mother is in the room or something. "Would you be interested in me coming over to watch football?"

"That'd be cool. Should I bring Chris over?"

"No. Not this time. Later, definitely. Today it will be just you and me." I didn't mention my husband Dan would be with us this time, looking on. Didn't want to spook the kid.

The next thing that went through my head was what I should wear. Most days when I am just lounging around the house, I don't wear much. My normal attire is one of Dan's dress shirts and nothing else and this day was no exception. It was a blue Brooks Brothers shirt, button down collar -- you know the deal.

I went into the bedroom to put some clothes on. I laid out some jeans and a top. Then while looking in my underwear drawer, I thought to myself, 'Why bother?' Whatever I put on probably wouldn't stay on very long after Tommy got here.

I decided to just go with the shirt, a black miniskirt and a pair of black lace panties, and spent the time with my hair and make-up. I undid a button to let more than a little bit of cleavage show, and then I went downstairs.

Dan eyes went up and down "Very nice!" and he told me I looked sexy.

I have to admit I was nervous and Dan seemed even more nervous. This would be the first time we went through with it - 'did it' - with Dan in the room watching. Dan sat in his favorite chair and I sat on the couch. Tommy seemed to be taking forever to get there. I reminded Dan that this was something he wanted, but once we went through with it, we'll have crossed a line we can never go back across. He assured me this was something he really wanted. Then came the knock on the door.

I answered the door. Tommy smiled, he's such a nice kid, and I let him into the foyer before I let him kiss me. I'm sure he could tell I wasn't wearing a bra under Dan's shirt when we embraced.

We went to the basement Man Cave. I felt like I should have worn more clothes because with Dan there, I was suddenly uncomfortable with what little I had on. Tommy sat on the couch and I brought the guys some beers, and then we exchanged pleasantries and I left the room, let the guys watch the football game on TV.

I'm certain Tommy felt a bit awkward about the situation. He really had no idea the direction Dan and I wanted to take this thing. I'm sure the minute Tommy became aware Dan was there he thought it was just going to be an afternoon watching football.

Twenty minutes went by and I came back into the room, brought them both another beer and this time I had the shirt undone almost all the way down.

Dan broke the ice by saying to Tommy, "Do you like my shirt?"

Tommy gave a puzzled look and Dan said, "Not this one, the shirt Ann is wearing."

That made Tommy smile and he said it looked good on me. There was some nervous laughter and Dan offered, "You know she never wears anything under my shirts."

Tommy looked up at me and I nodded. I was too nervous to speak. I left the room, let them watch a bit more of the game. The next time I came down, I had the shirt unbuttoned all the way down and I'd taken off the skirt -- just the panties.

I sat back down by Tommy nervously knowing things had started. Tommy said I was very sexy and made an obvious gesture to adjust himself in his jeans. While doing that I said "You're really turning me on, Tommy."

He didn't reply. Instead he looked at Dan, confused.

Dan put his fingers to the unbuttoned front of the shirt and asked me directly, "Do you mind, Ann?"

"I don't mind if Tommy doesn't mind."

Dan gestured toward me and said, "You're our guest, Tommy. It's okay with me. Let Ann entertain you." With that he pulled the front of the shirt wide open, fully exposing my breasts.

I felt very awkward, my husband doing this in broad daylight with my former student Tommy watching. It seemed weird but I allowed it without objection.

I scooted a little closer to Tommy, lifted his hand to the open front of my shirt and placed it on my breast.

He caressed my breast, then hesitated and asked "Are you sure?"

I looked at Dan, who was watching intently, and then said to Tommy, "No one's going to stop you."

Tommy slowly caressed my breasts. "MMMMmmm," I moaned, "My titties are just dying to be kissed."

With that Tommy leaned forward and began kissing my bare breasts, sucking my nipples. I looked over at Dan who was still watching intently and felt a thrill course through my veins. The breaking taboo aspect of it all was sending me.

Sensing no objections, Tommy slid his hand up to my panties. I spread my legs to give him room to insert a finger into me. It easily went in, if that tells you anything. I was turned on but couldn't help but feel strange at the same time. I felt slightly embarrassed about being felt up and fingerfucked with my husband sitting right there next to me, watching me being turned on.

After several minutes, Tommy moved off of the couch and onto the carpet. He pulled my ass forward, pulled my panties all the way off and began licking my pussy. This felt even stranger to have happening while Dan was watching. Tommy is quite good at it thanks to the lessons I've been giving him. It felt good and I had an orgasm building.

Again it seemed really strange but I was enjoying it and began bucking my hips into him. It is a lot different to have an orgasm with your husband then it is to have an orgasm in front of him. In that respect, Tommy was incidental. I felt more embarrassed about having an orgasm while Dan watched than about Tommy giving me one. Still, I came. It wasn't a huge one but it was good. Reluctantly, I had to push Tommy's face away and he sat back on the couch. The orgasm had only served to raise my level of arousal.

Tommy wiped his face off on his sleeve. Then I slid my hand up his thigh and said I probably should return the favor. We kissed while I opened his pants. Tommy whispered in my ear, "I want to fuck you so bad."

I answered, "I know," and slipped my hand inside his underwear.

Tommy removed my shirt completely. Even though the shirt wasn't covering much, it was still there. Now that it was off, I felt really strange being completely naked.

Tommy shoved his jeans and shorts down to his ankles and said again, "I really want to fuck you." This time he said it loud enough for Dan to hear.

I placed my hand on his cock and said, "Let me give you sweet kisses first."

Then I lowered my head, parted my lips and took Tommy's cock deep into my mouth. That made him quite happy. Tommy sat back as I pleasured him orally.

I really like to suck cock, and I'm told I'm quite good at it. I sucked Tommy's cock deep into my mouth and hummed and moaned, then pulled back to the rim of the helmet, opened my mouth and worked my lips and tongue around his rim.

Pulling off, I continued to stroke Tommy's wet length as I turned to my husband and said, "He's bigger than you, you know." I thought maybe this was part of his kink. "I'm going to really enjoy fucking him."

Then I took Tommy's cock into my mouth again, made his rod all wet and slobbery. He was very hard.

I looked over to Dan as I slowly stroked Tommy's pole into my mouth. It was strange, making eye contact with my husband, with my mouth stuffed full of, my lips wrapped around another man's cock. As I sucked Tommy's cock, I regarded my husband with a look on my face as if to say, 'Is this good for you? Am I doing this right?'

Finally I pulled off. Holding Tommy's cock before my lips like a microphone, I looked up to him and said, "Please fuck me now."

Tommy reached forward to take my hand, lift me to my feet. I stood fully nude in front of my husband and my teenage lover, reveling in the thrill as their eyes roamed my naked body.

I hiked a leg over Tommy as he sat naked on the couch with his big beautiful cock poking straight up in the air and lowered myself onto him. As I guided the head of Tommy's hard, hot meat into my wet pussylips I looked directly into my husband's eyes and whispered the words, "I love you."

Oh my God how good Tommy felt as I impaled my wet pussy upon his hard pole. Tommy put his hands on my tits and I held them there with my own as I rode up and down on his shaft. I was already beginning to orgasm; my peak was very close.

Tommy moved his hands down to squeeze my asscheeks. His fingers found the crack of my ass, a finger probed deep into my asshole.

That did it put me right over the edge. I clasped Tommy's hands hard on my ass as my pussy started squirting all over his pole. I cried out, eyes squeezed shut, "Ah! Ah! AHHHHH!!!!" Waves of pleasure coursed through my entire being.

Finally I could take no more. I collapsed over Tommy, put my arms over the back of the couch and smothered him in my sweat-covered breasts. "OH MY GOD! OH MY GOD! OH MY GOD!" I sobbed.

When I recovered a bit the first thing I did was hold Tommy's face in my hands and kiss him, long slow loving soul kiss.

Tommy was still hard and he was still in me. I slowly lifted myself off -- I was so sensitive ooh it felt as good coming out as it did going in -- and dismounted. I went back to my place, on my knees before him.

Holding Tommy's hard throbbing cock before me I placed a little kiss on the very tip and some pre-cum dribbled out. I looked my husband in the eyes as I licked up the shiny liquid. "I want to finish Tommy off this way, Dan," I said.

My husband was transfixed. He could barely whisper, "Yes . . ."

I took Tommy's length into my mouth and made him very wet, lots of slobber. Then I began jacking Tommy off into my parted lips. He didn't last long.

Tommy moaned as he began cumming all over my outstretched tongue. Thick gobs of jizz, yummm. Most of his hot cum landed in my mouth -- I swallowed of course -- but a lot of it splattered all over my cheeks.

I looked over to my husband lovingly as a thick line of goo dripped down my chin and puddled up on my heaving breasts. Dan had a look of incredible intensity on his face, like a panther ready to pounce on its prey. If I live to be a thousand I will never forget that look.

Tommy was very pleased with his blowjob, naturally. He was sitting back with a glazed look in his eyes, his big cock still semi-stiff. I licked him clean, all the while looking my husband in the eye.

Shortly after that I walked Tommy to the door, completely nude. Why bother getting dressed? There was still Hubby to attend. I hadn't even wiped off; his wad was still splattered all over my cheeks, my chin and my breasts when I kissed him as he left.

Dan was standing there waiting for me when I returned to the basement. He kissed my cum-splattered face, then forced me down on the sofa and made me undo his trousers and give him a blow job. It was a good face-fucking, my wet mouth all around his pole.

I was right, he didn't last long.