Learning about jacking off Part 25 Boys Night Out

Dad suggested I be out of the house 'with a friend' and he would pick me up down the street. "No need for your Mom to know we are going out together. She might not think that was a good idea." I agreed with that and was waiting on the corner where I usually caught the bus to meet my clients.

Dad pulled up minutes after I got there. He was in a great mood. He started talking about what we were going to do. He flipped a pack of rubbers to me and said, "You will want to use these tonight. If you don't know how they work, Melody is very very helpful." I said okay quietly and he slapped me on the shoulder and said, "Hey bud...don't worry about this. The most natural thing in the world. Melody knows you're a virgin so she will be very gentle with you. I have paid for the whole night. I have to be home by 3:00, but you can stay all night if you wish." He laughed again and said, "I am so fucking excited. So...you jack off Peter? Got to be doing that...I was jacking off when I was younger than you are now." I laughed and said, "Oh I get off all the time Dad."

We went way out of town and finally were going down a dirt road that was long and a bit bumpy. We passed a bunch a trees that came into view and there was a large house with five cars parked in front. Dad slipped me a twenty and said, "Melody is already paid for Bud...this is for the tip." I nodded my head and was actually kind of intimidated knowing I would be fucking a professional.

When we walked in Dad and I walked over to a large woman with too much make up on her face. Her name was Annette. Dad seemed to know her really well. He said, "Well...I brought the boy in for his first time. Peter...meet Annette. She grinned at me and said, "Well, well, well...what a handsome young man. Just how old are you Peter?" Dad had told me to say nineteen so she could pretend that this was all on the up and up. "Nineteen...I'm nineteen." I was acting a little nervous, but it wasn't all an act.

Annette picked up a phone and soon two beautiful women came into the room. One of them walked directly over to Dad and kissed him. She had dark hair that was braided in pigtails. Her eyes were brown. She was wearing an indigo blue dress. "Melody, I would like for you to meet my son Peter." She walked over to me and took my hand in her warm soft hands and squeezed it gently. "It's a pleasure to meet you Peter. Your father has mentioned you to me. I am very honored to be your introduction to the world of the love arts."

I was now genuinely nervous. I stammered a bit as I thanked her and said I was very excited. Everyone but me laughed. Melody's laugh was a very polite one. She put her arm around my neck and her mouth to my ear and whispered, "I am so excited to meet you Peter. I love fucking virgins. I was one myself not that long ago." She kissed me on the cheek and took my hand. She turned to the others and said, "Peter and I are going to retire to my room. If it gets noisy in there try to ignore it." She giggled and so did I. As I looked back I saw walking away with a blonde who had huge tits and long legs.

As we walked she asked, "So do you have a girlfriend Peter?" I thought about that and said finally, "yeah the girl next door." She asked me to tell about that girlfriend. "Her name is Ellen...she's about my age." Melody asked if I had ever kissed her and I nodded my head. "Ever get to second base with her Peter?" I honestly didn't know what second base meant, so she told me. "First base is kissing. Second base is touching above the waist. Third base is touching below the waist and fucking is a home run." I decided to play it chaste and said, "Well, yeah once." She smiled and said that sounded nice. "Did she like it?" I told her she liked it because we were also kissing.

"I don't do first base...it's just a rule I made for myself. I only kiss the man I love...and he isn't often around. You can have all the other bases though Peter." I smiled and said that would be great. My cock was dangerously hard...I could have cut glass with it. We got to a door. She opened it and said, "Welcome to my little den of sin Peter."

I walked inside and sat down on the pink bed. Melody stood in front of me smiling. She put her hands in my hair and pressed her clothed breasts to my face. Her nipples were hard and easy to see though the thin fabric of her dress. I reached up and put my hands under her tits. "Second base!" I said happily. She laughed and told me "No silly, second base is when the tits are naked. Was the second base with the girl next door with your hand on top of her clothes? I nodded my head. She pulled the bodice of her dress under her tits. Her firm and gorgeous tits were staring me in the face. I couldn't help myself and pulled her right tit to me and started sucking on her nipple. She put a hand on the back of my head caressing it as I sucked on her.

"I love having a first timer. Everything is so new. If you reach behind me you will find my zipper. Pull it down so I can drop this dress off." I did so and she stood naked except for her sexy panties. I knew those panties were from a boutique online. Several of my clients wore them. Melody knelt on the floor in front of where I sat on her bed. She untied my shoes and removed my socks. She rubbed my feet gently and that felt so good I decided to add that to my repertoire.

She unbuckled my belt and asked me to stand up. She undid my pants and slid them down my thighs. My cock was hard and raging under my shorts. "I see you are enjoying this Peter." She stroked my cock through the cotton shorts. She traced the head and slid a finger down the underside of my shaft. "You have a very nice cock there Peter." She peeled my shorts down my legs. My cock was against her forehead as she started licking my balls. That was very nice. She slid her head up so the shaft moved down from her forehead, past her eyebrows, down her nose and came to rest on her lips surrounding her open mouth.

"I want to suck your cock Peter. Would you like that?" I smiled, trying to look a little nervous. She tilted her head back and closed her lips over the head of my cock. She moved the tip of her tongue on the slit at the tip. She swirled her tongue around the head. I stood there with my hands at my side trying to resist the urge to hold onto her head and fuck her slut face. Melody was the best cock sucker I had ever been with. She moved her mouth slowly down the entire length of my it. I felt the tip against the back of her throat. She moved her hands to my ass, caressing the cheeks.

She pulled her face away from my cock and said, "Peter, if you feel the need to come down my throat that is perfectly all right with me. If you feel the need to hold my head and fuck my face that is all right too." I tried to look confused at that so she added. "I know you haven't fucked a pussy yet Peter. I am sure you know the mechanics of that and have thought about it many times. You will be able to fuck my uh pussy as often as you want tonight. Just don't be shy about taking over...if you feel the urge to do so." She winked at me and started sucking my cock again.

I decided to play it cool and be a virgin. I almost came several times, but was able to hold back by thinking about math class. Finally Melody had just the head in her mouth. She moved her tongue all over the head. She had her hands on my shaft and with the tips of her forefingers she stroked the sensitive tissue below the head. It felt fantastic! She winked at me as she saw my excitement. She continued moving her fingers over that spot and suddenly I HAD to hold her head as my semen jetted into her mouth.

I collapsed back onto the bed. Melody stood up then and cupped a hand under her mouth. There was a large pool of semen on her palm. She rubbed her hands together and worked the semen onto her face. "It's good for the skin...as well as only eight calories for as much as you gave me Peter. So did you like that?" I smiled and said "It was GREAT!"

She stood up then and I saw that her panties had become very wet. They were pink, but the pink in the crotch was a different shade from her juices that had soaked into the fabric. Melody got up then and opened the drawer by the side of her bed. She pulled out what I know now was a joint. She lit it and handed it across to me. She saw my confused look and said, "It's pot. It won't hurt you, but it makes you feel really good. Take just a little and then inhale it."

I took a little into my mouth. When I inhaled it I started to cough. She laughed and said, "If you don't cough you don't get off." I took another puff into my mouth and inhaled it again. This time I coughed less...and I felt funny in a very good way.

"Want to see my pussy?" She asked dreamily. I nodded my head. I was lying back on the bed. She crawled over me and her wet panties were right over my face. "You can pull them down Peter. Just move them down my thighs and I will get them the rest of the way off."

I did as she asked. After fucking all those older women it was nice seeing a pussy that was closer to my age. She had done a Brazilian wax job on it and it was just fucking gorgeous. She leaned back and pulled the panties down to her knees and after several movement got them off completely. She was squatting over my face now. "The perfume you smell is the smell of pussy. Most women will smell like this Peter. You may touch and explore all you want, but first let me show you around." I nodded my head. She laughed and reached down. Grasping her lips she said, These are my cunt lips. I use the word cunt because I love that word. Some women don't like that word so you will need to be sensitive to a woman's wishes concerning that." She spread her lips wider apart and said, "What you see just inside are my inner lips. Right here," She moved a finger to her clit,"Is my clitoris, more commonly known as the clit." Push a finger inside my cunt Peter. I did as she asked and found she was super juicy there. "The juices you feel inside are for lubrication during fucking. They are secreted by the Bartholin Gland inside my cunt. I am not usually this wet when I'm with a client. I am VERY wet tonight because you are new to this and this cunt wants to be ready for when you put your cock inside of it."

By this time my cock was hard again. I know you know I'm not a virgin Peter. Not much money to be made by a prostitute who won't fuck." She laughed and then said, "I was a virgin not that long ago. Next month it will be a year." She paused and said, "I never let anyone fuck me bareback Peter. Most of the guys who come in here have fucked all kinds of women. When I get a virgin though, I think it's nice to take a cock bare into my cunt. First of all I like the feel of a naked cock. Second of all, I know you haven't been putting it in places it shouldn't be, Third of all, it will feel nicer for you." She then asked me to sit up. She got onto the bed and lay on her back. She spread her legs. "This is the missionary position. That is how many boring men always fuck. I like it only as a change from other ways."

She got onto her hands and knees and said, "In this position, known as doggy style, the man kneels behind the woman and fucks her from behind. This is nice for both partners and is a favorite of mine. A man can hold onto the hips of the woman or even reach around and put his hands over her tits." She had me lay on my back. My cock was pointing up. She put her knees on either side of me and said, "This is the way I was fucked when I was a virgin. I was able to slide down on the man's cock and take it at my own pace. It's actually my favorite way to fuck. It's called Cowgirl. One advantage of this is that I can lean over you like this," She moved so her tits were right above my face. "You can suck on my nipples while I fuck your cock. It's your party Peter. What do you want for your first time?"

I liked where she was right then and said so. "Let's fuck like this Melody. I want to feel you move on me." She smiled and slid her cunt down onto my shaft. She dropped down an inch, waited, then dropped down another inch, waited, then moved all the way down on my prick. "How does it feel to have a juicy cunt on your hard cock Peter?" I smiled and said, "Great...now start moving. I really want to cum inside of you. She sat up and moved up and down on my prick. She was watching my face the entire time. I watched hers too, but loved how she moved her hips as she slid down onto my prick. Finally I started shooting up into her. She smiled lovingly down at me. "You look like a man that has just fucked a woman."

I smiled and nodded my head. We lay side by side for a while. Melody casually played with the semen inside of her as we talked. "How was your first fuck Peter?" I remembered the real first time with Mrs. Wilson and said, "It was great Melody." She asked me about my girlfriend. I told her about Ellen without telling her anything we had done.

I asked if she had a boyfriend. She was kind of shocked by that and then quietly said, "yes." "Does he mind that you do this Melody?" She shook her head and said, "He thinks I only sl**p around. He likes that. Sometimes he...uh...he likes to eat me out after I get home with a load in my cunt. Of course that only happens when I have a virgin client." I asked if she had virgin clients very often. She nodded her head and said, "You would be surprised at how many I get Peter. I am sort of the designated taker of virginity in this house. First of all I am younger than the rest of the women and second of all I always get good reports from my first timer clients."

I nodded my head,thinking about the first time clients and how they had all fucked her bareback, and remembering the time I had first-time clients. Does he like the taste then?" She grinned at me and asked, "Have you ever tasted your cum Peter?" I sheepishly nodded my head. She clapped her hands together and laughed. "Didn't like it did you?" I shook my head no.

"My boyfriend likes the taste of cum when it's inside of me. That way he can smell and taste my cunt as well as lap up the semen in there. You might be surprised Peter."

I nodded my head slowly. Melody pushed a finger into her cunt. It was coated when she pulled it out. She sniffed it. "Want to see what it smells like mixed with me?" I said okay. She moved the finger to my nose and I sniffed it. The smell of cunt was mostly what I got and that was nice. Melody put the finger into her mouth and licked it clean. "Want a finger of your own to taste Peter?" I was confused, but when she slid her finger into her cunt again and pulled it out covered in cream I knew I would try it.

It was actually not bad and I told her so. "He knows I have a 'date' tonight and that it will be an all nighter. He is hoping for a nice load in the morning...but...IF you want to...uh...take some of his dessert right now...I know I would love it...and I think you would too."

I thought about it and then said, "Sure. I want to try that Melody." She smiled sweetly. Melody grabbed several pillows and put them under her hips. She instructed me to lie on my stomach. I moved my head between her open thighs. Melody moved a finger inside her cunt and said, "You shot a huge load into me Peter. Take it slow." She was surprised at how well I ate her cunt. Licking the lips and the clit...but not too much on the clit." She spread her lips. My tongue moved over her fingertips and then into her cunt. My nose pressed on her clit. Melody gasped and held my head hard against her cunt as my tongue lapped inside of her. She was right... there WAS a huge load inside her. I lapped and got a great deal on my tongue. She had me do that for a while then asked if I would like to try what her boyfriend liked.

I shrugged and said, "Tell me what it is Melody. I might want to do that too."

She played idly with the pool in her cunt as she talked, "He likes to lie down and have me squat over his face." I nodded my head as I listened. "He likes when I use my pussy muscles to squeeze the semen slowly out of me. He opens his mouth and I try to hit the open target with the cum." I thought about that a minute. Melody seemed to be sort of excited about the idea of this with a virgin. Finally I said, "Let's try it. Let me taste the first drops and if I don't like it...I will close my mouth. Okay?"

She thought that was a good idea. I was surprised when I lay back and Melody stood up on her feet. She really was going to have to aim. She looked down at my face and I looked at her cunt. She squeezed some out that hung from her lips for what seemed like minutes. Finally a liquid pearl fell from those lips. I opened my mouth wide and actually caught it on my tongue. I closed my mouth, so Melody squeezed her lips together with her fingers as I tasted. I pressed my tongue against the roof of my mouth. It really wasn't that bad so I opened my mouth. Melody smiled when she saw that. She squatted a bit so she was closer to my face, about two feet above. Soon there was a large glob of cum poised to drop from her lips. I held onto her ankles and opened my mouth wide. About a tablespoon of cum landed right on the left edge of my mouth, part in, part out. I used my tongue to get the come on the outside into my mouth.

"Nice catch lover! You have a hard cock too. How about some sloppy seconds Peter. Fuck me while there is a nice load of cum inside me." She eased her juicy cunt down onto my cock. The sound was really sloppy and sounded so cool. She started kissing me, lapping at the cum on my tongue while moved her hips up and down on my prick.

It was then that I noticed the door was open. Standing there in the doorway was the blonde and my father. I didn't think they had seen the cum squeezed into my mouth, but they certainly were watching me fucking an obviously already fucked cunt. I turned my head so they wouldn't see me watching them watching us. The next time I turned my head the door was shut.

The phone rang. Melody kept moving her hips up and down on me as she picked up the phone. "Uh...I don't know...let me ask." She looked at me, still moving her cunt up and down on my prick, "Your Dad needs to go home now. Do you want to stay all night? I can give you a ride home in the morning if you like."

The idea of staying all night in her room sounded wonderful to me. "I'll stay." Melody relayed the message, hung up the phone and we fucked until I had shot another load inside of her.

"You are a fast learner Peter. I have actually come four times tonight and I almost never really do that with a client. I always fake it, but no need for that with you. She asked me if I would do something for her. I told her I was up for almost anything. She asked about how long I had been jacking off. I told her it had been just a little while actually. She asked if I looked at pictures when I jacked off. I thought about the pictures Mom had given me and said,"Yeah."

"Something I really like Peter...something I did with a special person long before I ever lost my virginity...that something I really like is for a guy to stand or kneel over me as I lie on the floor and jack off onto my face. I love that. Would you do that for me Peter?"

Finally something new! "Let's go Melody." She lay down on the floor. I knelt over her, my inner thighs touching her tits. Melody started talking. "Oh yes ...play with your hard cock. I want to see that milk squirt out of the end of your thing. Please!"

Listening to this woman and watching her face as she pleaded for me to shoot all over her face was very very hot. This was only the second time I had jacked off since cousin Tom had taught me. I smiled when I remembered him saying, "You don't fuck a face Peter." I wasn't fucking this face but I sure wanted to shoot my cum all over it. I was pounding my cock furiously and finally shot ropes of cum all over her face. Some got into her left eye. She used a finger to get it mostly out of the eye then licked the finger off.

I helped her stand up. We walked into the bathroom and she smiled broadly at seeing all the streams of semen on her face. "I am going to let the semen dry on my face Peter. We won't be kissing anymore tonight because my boyfriend will want to clean me up tomorrow." I thought that was odd, but found I enjoyed seeing my cum on her face as I fucked her again and again.

In the morning we drove to a fast food restaurant. Melody ordered breakfast burritos for us. She was well aware of the people staring at the cum all over her face. When we drove away she said, "Well...I made THEIR morning. I wonder if that brunette will be playing around during break with the guy making the coffee." We talked about how that would work, laughing as we went down the street where I lived. I had her drop me off where Gloria always did.

I gave her the twenty and thanked her for a great night. "Tell your boyfriend I said 'Hi'" We both laughed. She patted her crotch where she had stuffed panties inside to hold onto the semen. "He's going to just LOVE this. Thank you Peter. I'd like to see you again sometime. Remember to use a rubber when you finally fuck your girlfriend. Not a good time of life to be a Daddy. Got to shop around...if you know what I mean.

I got out of the car. She waved as she drove away.