Seduced by an Experienced Woman Ch. 06

Ann carefully stretched the skin of my scrotum and shaved off every last hair. She rinsed and dried and applied a cool skin cream all the while teasing first my cock and then my balls and every so often massaging a very tight anus. When she was satisfied with her efforts she playfully slapped my butt again. "Let's get another picture now!" She took a closeup of my now smooth hairless balls. "Wait till Carol sees this!"

Ann took the pan of soapy water back to the bathroom and returned with a can of baby powder. "I don't want you getting a rash."

"Now you're ready to be milked!" She informed me with obvious satisfaction. She began applying a lubricating jell to my cock. I was getting harder by the second. "Turn over."

Eyes closed, half in a trance I mumbled, "What?"

"Assume the position Freddy!" She giggled excitedly. "Face down on the bed, ass in the air and spread'm." I rolled over and she slapped my ass again. "That's it! Very sexy!" She placed the towel on the bed under my belly and began stroking. Her other hand was massaging my balls. "Whenever I milk you this is the position you must be in! Don't forget."

"Yes, ma'am." I moaned in approval.

Ann's left hand treated my cock like a milk cow's teat. Her thumb and forefinger made a circle around the base of my cock and tightened as she pulled down. Her grip softened as her hand move back to the base of my cock. Her right hand was either rubbing my balls or pulling on them to keep them from drawing up. The effect was exhilarating and frustrating at the same time. My cock was ready but my balls weren't quite there. "Freddy likes?"

I moaned again. Before I could reply she was spreading the lubricating jelly on my anus. Her finger kept pushing but didn't intrude. "That feels so g.o..od!"

"And this?" I felt something slip into my ass.

"Oh, y.e..s! What are you d.o..i..n..g?"

"Getting ready to massage your prostate."

"My prostate?" I asked, wondering what she meant.

"I told you Freddy, I'm milking you. I have to massage your prostate to completely drain you."

I wasn't complaining. She stroked slowly and pushed gently. Something was filling my ass! She pulled back and then pushed again, deeper this time. "Does that hurt."

"Ahhh... not at all; it feels good."

Slowly she worked her way into my ass. I realized she wasn't using just her finger. "What is that?"

"A little dildo." She answered like it was the most natural thing in the world. "I can't stick my finger in there. It's not clean and I wouldn't want to nick you with a fingernail."

I wasn't as sophisticated as I thought, "A what?" I arched my back as all sorts of thoughts entered my mind.

"A dildo Freddy, you know girls masturbate too don't you?"

"I guess so." I hadn't ever given it much thought. Especially since I had been taught it wasn't a good thing for boys to do.

"Well, sometimes we need a little toy like this to touch spots we can't reach." Ann explained without any shame.

It felt so good I didn't really want to resist so I just moaned again. My cock was sending signals I wouldn't last too much longer.

Ann could feel that my cock was nearly ready. "Freddy?"

"Yes?"

"Hold still; I'm turning on the vibrator." Cum poured out of my cock as Ann continued the stroking motion on my cock and the fucking motion in my ass gently massaging my prostate until there was nothing left. I collapsed. Ann turned off the vibrator but left it in my ass as she massaged my back. "Are you OK?"

"I'm more than OK; that was incredible."

"I'm glad you like it!" She slapped my butt once more as she got up to take a shower.

"I'll be right there."

"Not this morning Freddy. After I've had my shower I'll go start breakfast. You rest a few minutes and then take a shower."

I relaxed and listened to the shower. In less than a week Ann had changed my world. My soon to be ex was two years my junior and all the girls I had ever dated were younger too. I was starting to understand that older women need love and they had the advantage of experience!

When Ann finally returned to the bedroom she was wearing a sweat shirt, jogging pants and running shoes. I got up to give her a hug but she pushed me away. "Not until you've had a shower; you're a mess! And put that towel in the clothes hamper. I don't want the girls to see it when they get home tonight!"

"As you wish, Mistress Ann!" I bowed half in jest.

She cocked her head smiling, "Good boy! One more thing Freddy."

"Yes ma'am?"

"Wash the dildo with soap and water and then wipe it down with the alcohol next to the sink."

"As you wish, Mistress!"

"When it's clean put it in the night stand."

"Yes, Mistress."

I washed the dildo and wiped it down. When I opened the nightstand drawer to put it away I found another bigger, longer dildo that looked like a cock. There were other toys as well as some scarves, handcuffs and blindfolds. My cock began throbbing just thinking about what might happen.

I closed the drawer and went to take a shower feeling a little strange because Ann wasn't washing my back and teasing my cock and balls. And wondering what else might Ann want to do. All I had with me was a change of underwear but even that was down stairs next to the chair by the door so when I was dry I went down to join Ann in the kitchen. I grabbed a hair brush and went to the lavatory next to the kitchen.

"Don't you look nice this morning!" Ann teased when I joined her at the table. Breakfast was oatmeal with raisins and chopped pecans with a hint of brown sugar and some milk. There was orange juice and coffee too. Ann wanted to talk about the double near the campus so we talked business until her doorbell rang. It startled me. An obvious look of concern was all over my face. "Who is that? You're not expecting anyone are you?"

Ann put her hand on mine. Her tone changed from light and cheery to serious. "Listen carefully Frederick, we've had a very nice week. No matter what you decide we will continue our business relationship but if we are to continue, if we are to take the next step in our personal relationship you will need to trust me. I promise I will never hurt you. I will honor my promise to never have sex with anyone but you and I will expect you to honor your promise to me."

I tried to speak but Ann interrupted, "Let me finish." She said sternly. "Carol and I go jogging around the lake every Sunday morning. When we come back we will seat ourselves in the living room and you will serve us coffee and the danish on the counter dressed just as you are. You will not speak unless spoken to and you will do everything we tell you to do. If you decide you can not do this for me please get dressed and leave. You can call me tomorrow about making an offer on the double." Without letting me answer she stood up squeezed my balls and never looked back as she left to go jogging.

I had no idea how long she would be gone. All I knew was that I had never in my life enjoyed sex as much as I did with Ann. She was in no way shy. She enjoyed playing with my body as much as or maybe more than having me play with hers! She was an active participant. Every other girl I had ever known was passive. They would let you know just what they would allow but it was always a guessing game.

Ann was different. She knew what she liked and she wasn't at all shy about letting me know what to do. There was no guessing. There were no games. The very first time we fucked she fucked me! Sex at her age was about giving and receiving pleasure and truth be told I wanted more! I had no idea what introducing me to Carol did for Ann but the idea had a strange appeal.

I've since learned that some men want to be humiliated and being naked with clothed women does that for them, especially when the women enjoy belittling a man. That was something I did not want or need but was it something Ann wanted? There was only one way to find out. I started making a fresh pot of coffee.

I found a tray in a cupboard by the sink. There was a place mat in the drawer that fit the tray. I found two cups and saucers and two spoons and put them on the tray.

There was a cream pitcher and sugar bowl on the counter so I put them on the tray as well and got some milk out of the fridge. There were napkins in the same drawer as the place mat so those went on the tray as well. I was ready if only the coffee would finish brewing!

"Frederick! I'm back! Come to the living room and meet my girlfriend, Carol."

She seemed so sure that I was still there. She told me later that my car was still outside and my clothes were still on the chair so unless I ran out the back naked I would still be there.

I thought to myself, "How is it possible for a naked man to calmly and with dignity, any dignity at all, enter a room to meet a strange woman?" I was about to find out.

As I walked into the room Ann and her friend Carol were already half way a crossed to meet me. "Frederick. I'd like you to meet my jogging partner, Carol."

"Carol, this is Frederick, the real estate agent I told you about. Frederick, this is my friend Carol, I'm sure you remember... the friend you talked to last night." There was no mention of my nakedness by either woman and neither of them seemed the least little bit uncomfortable.

For some strange reason I was not excited at all. It was like I was in a trance.

Carol didn't even glance at my crotch. "Ann has told me so much about you, Frederick." She said politely offering her hand; just like everyone says and does on a first meeting.

I took her hand politely and shyly replied. "Please, my friends just call me Fred."

"Carol is a professional photographer? We met when she started taking pictures at the store for our weekly ads. Over the last three years as we've grown to know more and more about each other as we've become very close."

I just stood there, motionless.

"Frederick." Ann brought me back to reality. "Say something!"

"It's nice to meet you, Carol." I am so bad at small talk. I had no idea what to say to a woman who talked to me over the phone about oral sex.

"It is pleasure to meet you, Fred, especially after our little talk last night!" I am sure I turned beet red at the mention of our less than appropriate phone call.

Carol smiled wickedly and changed the subject. "Well Fred, I'm thinking about investing in rental properties too. Do you suppose you might be able to find some for me to consider."

I looked at Ann for guidance, word of mouth recommendations are the best kind but this wasn't the kind I ever imagined. "She's serious Fred."

"I would be glad to Carol." I tried to act as if this was an everyday occurrence. "Would you ladies care for some coffee and danish?"

"That would be very nice, Fred." Carol said, smiling.

"Bring it in here, Fred. Carol and I have a few things to talk about."

As I put the tray on the coffee table Ann asked, "Did I tell you Carol is a professional photographer?"

"Yes, you did!"

"Well, she likes the pictures I took of you." They were lying on the table. Not that it made any difference at this point.

"You're a good looking guy, Fred. And so under control. Most men would be getting hard sitting with two clothed ladies and not wearing a stitch." This was the first mention of my lack of clothing and my penis which while not hard was swollen.

"Fred would be too, Carol, but I milked him a little while ago." Ann explained our activities as though she were discussing a shopping trip.

.

"Really! How was that, Fred? Would you rather fuck Ann or get milked?" Carol wasn't shy either. In a strange way they relished discussing such an intimate subject without belittling me.

I'm sure I started to blush.

Before I could answer Ann piped up. "I don't think that's a fair question, Carol. Would you want to choose between a really good fuck and having somebody who knows what they're doing eat your pussy?"

"Why can't I have both? Carol wondered, "Andy's a good cunt licker and he can fuck."

"That's true, Carol, but guys usually cum once and then they need a rest."

"Do you think Fred would like to pose for me?" Changing the subject again, Carol asked Ann instead of me.

"I think that's a wonderful idea, why don't you ask him?"

"Have you ever done any modeling, Fred?

"Ah... no... I haven't."

"I'm surprised, Fred. You've got such classic features and your eyes are beautiful!"

"Thank you."

"I'd really like you to come to my studio sometime. We could do a few test shots. If you'd like I can take make a portrait for you to use on your advertizing."

That was something I hadn't been able to afford yet and I did need one. "Well, I suppose but I don't know a thing about modeling.

"Nobody does when they start." Carol assured me smiling, "I use guys and gals in some of the layouts for clothing and sporting goods ads. You might be surprised, it could turn into a nice part-time job."

Ann chimed in, "I think it's a wonderful opportunity, Fred, think about it, OK?"

"I'll give it some thought." I allowed.

"What time is it?" Ann wondered.

"Almost ten." Carol informed her.

"Aren't we supposed to meet Andy at Tee Jaye's for brunch at ten-thirty?"

"You're right! We can still make it if we hurry!"

"Let's go Freddy, get dressed!"

Brunch with Andy was completely unremarkable. When Carol introduced Andy she explained that he was one of the warehouse men at Ann's store and that he had done some modeling for her too. The conversation was boring at best. I do remember thinking that Andy's relationship with Carol must be something like mine with Ann. I'm sure he thought the same of me. To others it was just two twenty something guys having brunch with two middle aged women who were not quite old enough to be our mothers. Two very good looking, sexy middle aged women to be sure but there still was an obvious age difference. Before leaving Carol asked Ann, "Would tomorrow or Tuesday be better for our first session?"

"What do you think, Freddy? Tomorrow or Tuesday?"

"For what?"

"Don't play hard to get, Frederick! You know very well what Carol is talking about! She wants to take some test shots to see if she can use you in some of the ads she is doing."

Without actually agreeing I chose, "Tuesday would be best I guess."

"What time should we be there, Carol?"

"The studio closes at eight. Give me a half hour to get a bite to eat. Eight-thirty OK?"

"Eight-thirty it is. That's OK with you, Freddy?"

"That works for me; unless I get tied up with a client."

"You don't have to tag along, Ann."

"I want to, Carol." Ann was suddenly serious, "I don't think I can trust you alone with Fred!"

"Don't be silly!" Carol laughed, "My assistant Ashley and Andy will both be there."

"All the more reason for me to tag along!"

Andy grinned knowingly.