Educating Tom Ch. 01byBeejayne©
My husband and I have done the swinging scene over the years and I've enjoyed it, although he is really the instigator most of the time. He's always finding men for me in one of those throw away papers. You know the sort of thing, they're usually full of radical articles, columns, and letters and ads, and in the back are sex ads: "Couple would like to meet hot, hung male for......" and "Bi-girl wants to meet pretty woman, any age, for mutually satisfying sex." And so on. In our local paper there are several pages.
Gar presents an interesting ad to me from time to time. Most of them I reject, but once in a while there's something interesting and from time to time I have a new lover or we have a new playmate.
Recently he looked up from reading the ads and said:
"Here's an interesting one Charlie." And held out the paper for me to read.
would like to meet mature woman to show me what to do. I want
her to show me everything from kissing to sex. Like slender women.
Please send photo with reply. Please reply to PO Box etc........
I should explain that Charlie is short for Charlotte and Gar is short for garcon, which his French parents used to call him. I looked at the ad and wondered if I should answer it. As a rule I didn't like to have sex with younger men because they form an attachment and get jealous, and I didn't need that. The other thing is that they can be more active than I'm used to and can wear you out. But for some reason this one appealed to me.
The PO Box was in Portland, and we went up to Portland from time to time. I answered the ad in a tentative way and sent a photo of myself, rather a sexy one, but in underwear, not nude. I explained that we'd be in Portland in a couple of weeks and that maybe we could meet and see where it went.
There was a sort of down scale motel we stayed at sometimes, especially for meetings like this one. Judging by the girls we ran into there it was used by hookers. There was a bar near it where they had decent food, and maybe we could meet there.
His reply came quickly with a nice photo of a tall young man with blond hair. He looked rather athletic and his reply was encouraging. I was getting very interested, and thought this might be pretty exciting. One drawback was that Gar wanted to be there and while that usually wasn't a problem with experienced men it might scare off this boy.
I wrote again explaining the position with my husband and got an answer in a few days. He didn't mind Gar being there he said, as long as there was no man to man stuff, which he wasn't interested in, and as long as Gar was not directly involved when we were "making love".
It was all set up! Now I had to get myself ready. We were going up to Portland in a couple of days. Should I do my hair? I decided to just touch it up because, while older men seemed to like red, red hair younger guys liked a more muted affect. Underwear? Again, older guys liked garter belts, but thigh high stockings might be better for someone so young. Finally a black bra and panties. A black blouse and short (not mini) skirt topped it off. I tried it all on and liked the affect. In fact I looked pretty damned sexy.
We got up to Portland on Friday afternoon and I phoned Tom just to be sure. Yes, he'd be at the bar at six-thirty. I changed into my sexy stuff and when Gar saw it wanted to fuck me right then and there, but I held him off. I wanted to be perfect and that would mess me up, especially "down there".
When we walked into the bar Tom was waiting and looked even more athletic that his picture. After we introduced ourselves we talked, the guys mostly about football. We ordered beer and then some food – hamburger and fries for me, found a table and ate while the two men still talked animatedly about football.
I finished eating and was getting ready to leave and Gar said he'd give us an hour and then follow. As we went out the door Tom took my hand.
"You look lovelier than your picture." He whispered in my ear.
I smiled at him in the light from the bar windows, "It's all artificial. You'll see."
Neither one of us could wait to get to the motel. We hurried up the stairs and passed one of the "girls" in the hallway and said "Hello". I opened the door and immediately we were inside he kissed me and I could tell right away that he hadn't kissed many girls.
His kiss was gentle and soft. I returned a firm kiss with my lips slightly parted and pressed my tongue against his lips. His lips parted and soon we were holding each other and French kissing. He learned what I wanted quickly and as our tongue met and caressed each other I could feel his hardness swelling against my lower abdomen.
"Learning to kiss is important when you're dealing with girls." I said quietly. "Now touch my breast through my blouse, touch my nipple and squeeze it lightly."
We kissed some more as he fondled my tit. Nice, very nice, and getting me hot, very hot. I undid my blouse and bra.
"Kiss them "I told him. "Kiss my tits."
He obeyed and without being told took a nipple in his mouth. I held his head against my breast and quietly told him to suck. Oh lovely! We must have gone on like this for ten or fifteen minutes, kissing while he caressed my breast, then he sucked my nipple while I held his head against me.
"I love your breasts," he said when we paused for a breath. "I love their shape and the softness of them. And sucking your nipples is really hot."
"It's hot for me too." I told him. "You can bite gently too, just sort of nibble as you suck. Doing things to a woman's nipples and breasts can make her really hot."
We moved back to the bed and I lay down across it, deliberately raising one knee so that he could see up my skirt. He lay down beside me and continued working on my breasts. We kissed some more while he caressed me but I wanted it NOW. Enough foreplay.
"Tom, take off my panties please." I asked him.
He hesitated then pulled back, pushed up my skirt and grabbing the waist of my underwear pulled my panties off as I raised my bottom. He paused and gazed at what he saw.
"Lovely! That's it then. That's what we all want." I felt him touch me. "It's so soft and so pink." His fingers were feeling my labia and opening them.
I felt a huge rush at the feel of his touch. I wanted his cock, I was aching to feel it in me, but I must remember that I was teaching him, I mustn't rush things.
"Take off your pants Tom." I told him, and I didn't need to say it twice.
"Just one last thing, Tom," I said. "You must put on a condom." When he hesitated I went on, "I've been with other men, Tom. I always insist a man uses protection and you must too, both for my safety and for yours."
While he did that I got up and took off my skirt. The condom thing was always a bit deflating, but necessary. I lay down again and Tom lay down beside me. I still had stockings and shoes on, but as I reached to take my shoes off he stopped me.
"Don't take your heels off, it makes you look awfully sexy." He said.
We kissed, hot and wet, all tongue. His hand caressed my breasts paying special attention to my nipples. That felt so good, and as his hand moved down over my stomach I felt it touch my pubic hair and finally rested on my labia and started to rub gently. This was driving me wild.
"Fuck me Tom. Please, fuck me now." And I opened my legs wide to accommodate him. He moved over to lay there and I felt his penis penetrate me, I gave a huge sigh of contentment and lust and his large penis spread me open. He started to move, in and out, in and out, slowly at first then speeding up until he was pounding me.
A wave of orgasmic fire shot through my body as I held him tightly in my arms and between my legs.
"Oh fuck that's good. Ah..ah..ah..ah.." I grunted in rhythm with his deep, hard strokes.
But too soon I felt him give several hard, hard deep thrusts and:
"Oh man, man that's good. Your cunt...Your cunt..So good. AAaaaaaaah that's hot. What a cunt!" As he slowed down. Then lay still between my legs. I tightened my legs around him and gripped him tightly.
We held each other for several minutes, then, still holding tightly moved to kiss. Not hard fevered kisses as before, but now gentle loving but still deep kisses. I felt him softening in me after a few minutes then he rolled away and his limp penis slipped out.
I rolled over toward him and whispered in hear ear. "That was super Tom, but you'll have to learn to last longer to satisfy a girl."
"I know," he said "But you had me so worked up I couldn't control it. I'll do better nest time."
"Shall we work on nest time now?" I asked him, and kissed his soft full lips, while I reached out to touch his limp penis.
We kissed and as I rubbed his penis I heard a key in the door. There were two sharp raps and after a pause the door opened. I kissed Tom once more then rolled back over away from him.
Gar walked in and looked toward the bed. "It's okay, we're still awake." I said.
"Good, I didn't want to disturb anything."
For the next few minutes we heard him in the bathroom, and I whispered to tom. "We could go on if you want."
"I think I'll give it a rest." He replied. "I'm sorry."
I was disappointed but went on stroking his growing penis. Maybe he'd change his mind, but when Gar came back in with his pajamas on I gave up. He got in bed and turned the light out.
"Everything okay?" He whispered in my ear.
"Yes, it was very nice." I whispered back. "Let me up, I have to pee."
He moved for me to get up and when I came back I put on my nightgown, and snuggled down in bed between the two men, very nice. I felt Gar's hand slide under my nightgown, but it just didn't seem right.
"Not now, tomorrow." I whispered to him.
We were soon all asleep, and I slept well, but in the morning I felt a hand on my leg. I still had stockings on and Tom's hand was slipping under my nightgown and found my bare thigh above the stocking. I moved my legs apart as his exploring hand found my pubic area and his fingers fondled my labia. I loved the feel of his strong but gentle fingers opening my lips and penetrating my wet hole.
I moved closer to him and our lips met. More kissing, he really has learned fast and knows what he's doing now. This is getting hot and maybe I'm starting to enjoy the fact that Gar is lying beside us, and is probably awake now.
I rolled over on my back and spread my legs. Tom's cock found its mark almost immediately and I sighed deeply as it penetrated my vagina. Oh that was so good, but where's the condom? Oh shit, the story of my sex life: a sad story of one pregnancy, an abortion and a venereal disease. But for now this is heaven.
As Tom fucks me I feel Gar stir. Who cares? With that steady, hard pounding I'm in love and Gar can jack-off for all I care at this moment. Tom's big and I'm enjoying the stretching my hole is getting, the raw flesh to flesh fucking with no rubber between my inflamed vagina and his bold, hard penis.
I can feel that big knob of a head going back and forth inside me and grab it with my internal muscles. I could go on like this forever and as I grip I have a couple of small spasms of orgasm, oh so good.
On and on he goes, this sweet dear, strong boy. I'm on fire, I can't get enough of him. We kiss again and again while his hands caress my breasts. And his penis thrusts in and out of my vagina. Then I start to feel the heat well up from between my legs and I clutch him tightly to me. This is it! My muscles grip him tightly and as he plunges into me deeper and harder I'm overwhelmed with a consuming orgasm.
"Oh Tom, Fuck! Fuck me hard...Uh ...uh...uh.." I pant out. He complies by banging me harder, almost bruising my mound.
I have several gripping spasmodic seizures and relax my whole body and go limp. Tom continues fucking me hard. Until:
"Oh fuck yes! Oh that's good. Oh yes! Oh yes!. There! Aaaah. Oh so, so good." I felt his sperm fill me, it squirted warm, splattering my insides – or at least I thought so.
I lay still. It's over. We both continued to lie still, joined together by his still-hard penis. My legs still wrapped around him as it starts to soften. We kiss again.
Gar is the first to move. "I'm going to take a shower." He says as he gets up."
Tom doesn't move for a moment, but the he rolls off me.
"That was unbelievable." He says softly. "Masturbation was never like this." And he chuckled.
I lay on my back still and his hands touched my body until he found my sodden sweaty pubic hair. He gently touched my wet labia and pulled away.
"I think I'm in love with you." He murmured, and I laughed softly. I'd heard that many times.
Gar came out of the shower. "We're next." I sang out as I grabbed Tom's hand and pulled him into the shower. I could feel his juices dripping down my leg and felt very naughty being naked in front of these two men. I pulled off my stockings and threw them on the floor, then Tom and I got into the show and turned the water on full, nice and hot.
I took the soap and lathered up Tom's pubic hair and balls, and as I washed him I felt his penis start to swell and rise. In response he took the soap and lathered me up and I felt his fingers washing my slit. The slipperiness and hot water started to get me inflamed all over again. He was washing me all the way from my clit in front to my anus. So, so warm and good.
At the same time I held his penis and felt it getting hard. I turned around and bent over, gripping a handrail in front of me.
"Fuck me Tom. Please fuck me again."
I moved my legs apart and bent over more as I felt his fingers open my cheeks. I didn't want anal sex, but if he'd done that I would have accepted it. But, no, I felt his hard penis pushing against me and penetrate my vagina. With the hot water flowing over my body I gasped for breath as I felt him enter me.
He gripped my hips with his hands and with a firm thrust started fucking me. With each thrust I gasped, it was wonderful. He continued steadily, deeply shoving his hardness into me, but sometimes pulling back so that his large head just penetrating my labia, sending fire shooting through my body.
This went on until I felt him grip me hard and banged hard into my hot red hole. It hurt, it was good. I felt his sperm gush inside me (did I really?), as he had an orgasm, and still holding my hips in a grip that hurt, ground his penis into me as if he wanted to split me open. I hadn't reached a climax, but with a good fuck like this I didn't need one. Just doing it was enough.
We stayed locked together for several minutes, until he pulled back and I stood up. I stood with my legs spread apart and we both watched while his slimy stuff dripped out of me and was washed down the drain.
When we went down to breakfast together Gar paid for Tom to stay overnight and for his breakfast. This was a Continental breakfast, fruit, cold cereal and a variety of sweet rolls
The Indian owner/manager remarked, "I hope the bed was comfortable for all of you." As he took the money.
There were a couple of other guests who must have enjoyed his comments.