My Second Time Being Milked

Annie took my hand in hers. "Of course it is, darling. Let's have a nice dinner and then go back home and try out the table."

When the food arrived Annie asked Ashley to tell us a bit about herself. She was not from town, but from a smaller place some hundred miles away. She was doing her first year in college, majoring in finance. She wanted to go into banking after graduation. She had an on and off boyfriend, but promised us that he wasn't important in her life. Annie asked about her previous sexual experiences and she said she had lost her virginity before graduating High School with an older guy and since then had been with three guys. She said she wanted to expand her sexual experience and hoping that by being with us she would learn new ways to give and get pleasure.

All through the conversation I was staring at her. She looked at me a few times and I guess she might have felt uncomfortable. I just couldn't let go of how she looked like. I knew she was over eighteen, but she didn't look like it. When she stood to go to the bathroom, I saw that she was short, no more than five-five or six.

"She is too young," I said.

"Nonsense, you should have seen some of the things she wrote me, she is a horny little thing, that's for sure. She is perfect. Just relax and stop staring. By the way, did you see her boobs?"

"Not really, I was looking at her innocent face. What about them?"

"I think they are big. The pullover she is wearing is hiding them, but you just wait until she is naked."

"Uh-hu."

After I paid, Annie and I got into my car and Ashley followed in hers. It was a good looking Japanese car, some kind of hot hatchback. Not the kind of thing I had expected her to drive.

When we arrived at our house Annie suggested we all take a shower together. Ashley nodded and began to undress in the living room. I was the last one to be naked. I had a hard time concentrating on the buttons on my flannel shirt while Ashley was taking her clothes off, one item at the time. Under the pullover she wore a sports bra, and when she took it off her boobs exploded in my face. Well, not literally, but what I had guessed were A cups, turned out to be C cups. Under her skirt she wore white panties with a lace trim. And when they came off I saw a nice little triangle of pubic hair above her clit.

"What do you think," said Annie, and pointed at my cock.

Ashley walked over to where I was standing and without a word took my limp cock in her hand. She had hardly touched it when it rose and I was standing there with a hard on. She wrapped her little hand around it, and said. "Nice, I like the thickness."

I must have blushed, because Annie said, "don't be shy, Hans. Let's go to the bathroom."

It was cramped in there. We stood in the bathtub and soaped each other's bodies. I did Annie while Ashley did mine, and at one point Ashley offered to do Annie's back again. I thought that there was a moment of understanding between the two women. Maybe Ashley was into girls too, I thought. I wouldn't mind watching her going down on Annie. In fact, that sounded much more fun that being fucked in the ass.

"On the table, honey," said Annie, when we were back in the living room. It was dark outside, but she had drawn all the drapes just to be on the safe side.

I did what she said, and put my cock through the hole. I lay there feeling like a complete idiot.

"This is what I want you to do, Ashley," said Annie.

"Take this vibrator and make sure it has plenty of lube on it. Lube your finger and slide it in carefully. When he begins to moan you can gently introduce the vibrator. If he says stop, you wait a while."

"OK and how far should I stick it in?"

Annie giggled. "It's eight inches, and I'm pretty sure he can take it all, but you only have to insert it two or three. That's where the prostate is."

I became concerned. "Listen, don't get carried away, Ashley. Two or three is just fine."

Annie slapped my ass, and said. "Don't be such a chicken, honey."

Then she sat down under the table and I felt her hands on my balls and cock. It was semi erect but under her touch it hardened fast. Just as I was relaxing I felt Ashley's finger probing around my anus. I didn't feel any sharp nails which made me relax. She found my tight hole and began to push.

"He is tighter than I thought."

"Keep pushing," said Annie.

Her finger slid in and I breathed in and relaxed as much as I could. There was a difference between the two women. Annie knew where to go with the tip of her finger but Ashley didn't.

"You are looking for a walnut size thing, it's on the side of his tummy," said Annie.

She found it and I must have gasped. "You got it," I heard her say under the table.

"This is so cool. Let me know what is happening," said Ashley.

I closed my eyes and to be perfectly honest, it was much nicer than I had thought. Ashley was gentle and her little finger rubbed my prostate and it didn't take long before I heard Annie say, "Here it comes."

"What?" said Ashley.

"His pre cum, keep going."

I heard more than felt how Ashley looked under the table. "Oh my god, just look at that."

"What?" I said.

"The liquid is just coming out of your cock by itself, Annie isn't touching you."

The pleasure I felt was so intense that I hadn't noticed that Annie had let go of my cock. That strange feeling, like an itching in my cock, was becoming unbearable. Then Ashley decided to insert the vibrator, and turned it on.

What had been a nice comfortable pleasure in my ass, turned into an explosion of it. "Oh my, oh, oh, that is intense," I moaned.

Ashley began to slowly fuck me with the vibrator. "Do you like it, Hans?"

"Yeah, I do, I actually do."

"Good, because you are not dripping anymore, it's running free," I heard Annie say.

She wrapped her lips around my cockhead and began to suck. My breathing increased and I could hear myself moaning loudly. I almost felt ashamed for showing the pleasure I was feeling.

"Can I try some?" said Ashley.

Annie let go of my cock, and they changed places. "Are you OK, she said when she continued to slide the vibrator in and out of me.

"It's very intense, but I love it."

Ashley didn't just suck on my cockhead. She took as much of me inside her as she could, and played with my balls.

"Annie, I don't think I can hold back much longer."

She kissed my ass cheek, and said. "It's OK; you can come whenever you want."

I stopped trying to hold back, and said. "Ashley, I'm coming soon."

"Mmm," was all she said.

"Oh, yes, yes, here it comes," I moaned.

To my surprise Ashley didn't let go, instead she sucked harder and deeper and when I did shoot my load I heard her swallow as fast as she could. Then there was a wet sound and I heard her breath hard. "God, that was a lot of cum."

Annie slid the vibrator out of me and I managed to turn around on the narrow bed without falling off it. Ashley was standing now and holding on to the bed. There was cum on her lips, her cheek and on her chest. Annie walked around and wiped some of it off her boobs. Then she licked it off her finger. I closed my eyes and thanked my lucky star I had found someone like her and she had found someone like Ashley.

"When can we do this again?" said Ashley after we had showered, this time individually.

We were sitting naked in the living room. Annie and I were on the sofa and Ashley across in an armchair. She had her legs pulled up under her, but I had seen her cute little pussy. I wanted to fuck her so hard, but I wasn't sure how to say it. After all, this had been Annie's idea and for her benefit.

"Sure we can. What do you think, Hans?" said Annie.

"Yeah, of course."

"Today is Friday, what about Sunday afternoon? I need to study tomorrow," said Ashley.

I looked at Annie, who shrugged her shoulders. "Sunday it is."

"Cool. I have to go, but thanks so much, and Hans, you have a very cute butt, and I hope that one day, if Annie is OK with it, you will fuck me."

I was stunned. I just stared at her when she got up and put on her clothes. When she opened the door to leave, she turned and blew us a kiss.

"What a wonderful young girl," said Annie, when Ashley had closed the door.

"Yeah, she is."

She got up and was on her way to the kitchen when she turned around. "Would you like to fuck her?"

I was taken aback by the blunt question. "Well, yeah, I guess."

She grinned at me. "You dirty old man."

"C'mon, I'm not that old and you brought her here."

"I know, I was just teasing you. Sure, you can fuck her, but I want to watch."

Annie brought a bottle of wine and two glasses and after a while I got up and made us some dinner. We ate naked in the living room watching TV. My ass hurt a little, and my balls felt empty. I wasn't sure I would be ready for Sunday, but how could I say now to two sexy women? I had changed my mind about milking. It was something I could get into, especially with two women taking care of me. What I didn't know, was that Ashley had her own game in mind, and Annie would love it.

We had just finished lunch on Sunday when there was a knock on the door. Annie went to open while I cleared the table. I was a bit nervous, which was strange since I honestly looked forward to what was going to happen. I had spent most of Saturday day dreaming about plunging my cock into Ashley's young pussy. Annie had caught me with a vacant stare and had asked what I was thinking about. Being an honest man I told her and she laughed and said she was looking forward to watching us.

"Hi Hans," said Ashley, when she walked into the kitchen.

"Hi, you look great," I said.

She was wearing a mini skirt and a tight t shirt under a leather jacket. On her feet she had a pair of boots that ended just below her knees. She looked very hot.

"I have brought a gift. Well, it's a present for all of us to enjoy," she said, and held out a paper bag to me.

I put it on the kitchen table and looked inside. "Oh, this is a surprise."

"What is it?" said Annie.

I took out the box that was in the bag and showed it to her. "I guess Ashley wants to get close and personal," I said.

"Oh my god, a strap on, that is such a nice thing to buy," said Annie taking the box from me.

"I thought it could be fun, you know. We could both fuck him, and with the strap on it's our movements that bring out the milk. Not a battery driven toy," said Ashley, and her eyes sparkled.

I was glad to see it was not as big as the vibrator. It was shaped like a real cock, but according to the box it was seven inches long, and it looked a bit thinner.

Annie opened it and took out the harness and the dildo. She attached it to the harness and held it up in front of her. "This is so cool, I get to have my own cock," she laughed.

"I think we should skip the table, and just use the floor," said Ashley, and began to push the low table away from the sofa. Under it was a thick rug. Annie helped her and before I knew it, we had enough space to move around. Ashley helped me off with my clothes while Annie went to the bathroom for the lube.

"I'm so looking forward to fucking you. It's a fantasy I have had for a long time. I want to know what it feels like," said Ashley, while pulling down my boxers.

My cock sprang out and it was already hard. She grabbed it and stroked it slowly while looking into my eyes. "I want you to stick your cock into my pussy and ass today, Hans. I want you to open me up. I'm tired of the young guys and their inexperienced dicks."

"Just look at you two. You have to wait until I have had my fun," said Annie, who walked in just as Ashley knelt in front of me.

"Please, let me suck him," she begged.

"No, not yet. Hans, I want you to lie down on the floor, face up. I want to look into your eyes when I fuck your ass."

I did what she said, and Ashley was nice enough to find a pillow from the sofa and put it under my head. Then she got another and pushed it in under my hips.

Annie knelt between my legs and poured plenty of lube on my cock and balls. "Ashley, why don't you stroke him while I lube his ass?"

The young woman knelt beside me and took my cock in her small hand. She had a good grip, and began to stroke me while watching intently how Annie used her middle finger to lube my anus. I had to lift up my hips for her to reach, and I wasn't really clear on how she planned to fuck me in that position.

She slid a finger inside me and after a few minutes another one. I guessed my ass was used to it by now, because it didn't feel strange and it didn't hurt a bit. It just felt good when her fingertips touched my prostate. She continued to rub it and when Ashley smiled, and said. "Look, he is dripping," she pulled out her fingers.

Ashley lowered her face and licked the first few drops of my cockhead. "Mm, it tastes good."

"I need you to put your legs up on my shoulders, Hans."

I did what she said, and when they were in place, she leaned forward so my knees bent and I felt the dildo touching my anus. "Wow, do I feel like a bitch now," I said with a grin.

They both laughed, and Ashley said. "Relax, you are no one's bitch, you are a great guy, who let us fuck you and drink your milk."

Annie adjusted her body and said. "Let me know, when it's in place."

"Now," I said.

She pushed with her hips and my already lubed ass opened up and she slid in. "Oh, this feels much better than the vibrator. There is no pain at all," I said, with surprise in my voice.

Annie began to move with slow thrusts, not pushing in more than a few inches. "This feels so hot, Hans. I can't believe I am actually fucking you."

Her skin against mine, her movements and the dildo running over my prostate made me moan with pleasure. Ad to that Ashley's hands on my cock and I was close to coming in minutes.

"Annie, stop, stop or I will come. I want Ashley to do it, and you drink."

The women changed position and when Ashley entered me, she was not as gentle as Annie. She took hold of my hips and went to town with hard and long thrusts. There was still not much pain but after a while my legs began to shake, and an amazing feeling spread from my balls through my entire body.

"Just look at that," said Annie, pointing at my cock.

I lifted my head as much as I could, and I saw clear fluid coming out of my cockhead and running down my shaft. She lowered her head and licked it off. Then she moved up and took me in her mouth.

As I watched her suck my cock, her right hand moved up over Ashley's stomach until it reached one of her boobs. When she pinched her nipple, Ashley moaned and closed her eyes.

Annie sucked a bit longer and then let go of my cock. She moved around so she was behind Ashley and massaged her boobs and kissed her neck. The younger woman turned and they met in a kiss.

"Oh, Annie, can he fuck me now, please," she moaned.

"Are you ready to fuck her, Hans?"

I was so horny I didn't know what to do with myself. "Yeah, I'm ready."

"Then do it."

Ashley pulled out of me and moved up so she was straddling me. She was just about to grab my cock when Annie said. "Let me help you."

She guided my cock to Ashley's pussy lips and when I felt her skin against mine, she lowered herself slowly. My cockhead pushed in between her lips and when it entered her, she sighed. "Oh, fuck me, Hans. Fuck my young pussy."

That did it for me. I grabbed her hips and moved her up and down until I came inside her. Her fingers dug into my chest and she threw her head back, and came loudly. When she had calmed down, she got off me and lay on the floor and gasped for air. Annie moved up and lowered her head towards her swollen pussy lips.

There is something beautiful about two women being together. I lay there next to them, watching how Annie ran her tongue up and down Ashley's little pussy slit. I thought she would be exhausted, but she only needed a little bit of attention to come back. They moved into a sixty-nine with Ashley on top. Watching them turned me on, so I got up and drove my cock into Ashley tight pussy from behind. My balls slapped into Annie chin and face. When my cock was wet from her juices I pulled it out and slowly pushed it into Ashley's tight asshole. When I was all the way in, she turned and looked at me. "I love it; I hope you liked it as much when I fucked your ass."

"I did, and I want both of you to do it again."

"Just as soon as you have enough milk built up."

Again she came loudly and when I pulled out and shot my cum over her ass, she said. "That feels so good."

Then she used her hands to smear the juice all over her ass cheeks.

When Ashley had left Annie opened a bottle of wine. It was after eight at night and we sat on the sofa. She poured two glasses and put the bottle on the table. Then she took my hand in hers. "Hans, did you enjoy what we did today?"

"Yes, I did, I actually enjoyed it a lot."

"I'm glad you did. See, I told you that milking was something fun."

"Well, I don't know about the actual milking. If I'm not mistaken, I dumped the first load into Ashley's pussy and the second on her ass cheeks."

"You are so cute. I had plenty of pre cum while she fucked your ass. She was very good to be a first timer."

"I guess she is eager to learn."

"Next time, I will let her have the bulk of your milk and you can fuck me in the ass."

I kissed her and held her tight. "I can't wait."

Over the next months we would meet every weekend and the women would fuck me and sometimes each other with the strap on. What did I learn? That being milked is a fantastic experience if it is done by the right person or persons. I'm sure I will have new experiences with new women soon. Annie is talking about going on a cruise over the winter Holidays and I caught her checking if there were any swinger's cruises available.