Jack Helps a Friend - Cover

Jack Helps a Friend

Copyright© 2004 by Clvfan

Chapter 2

Erotica Sex Story: Chapter 2 - Donna is going through a bad marriage she gets Jack to help her out. the first time is a surprise for them both, what will happen next

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Romantic   Heterosexual   Cheating   Slut Wife   Oral Sex  

That seemed to set a pattern. About every couple of months she would come to my house and every time was as good as the first. About the last of November as we were cuddled in the bed, bodies sweaty, just enjoying the aftermath of some wonderful sex. She was kissing me, little gentle pecks.

Kiss, kiss,"Jack would you do me a favor?"

Kiss, kiss, "I was supposed to go to the Tim McGraw concert with Cindy."

Kiss, kiss, "and I can't go, Judy has a dance concert that night."

Kiss, kiss, "she won't go unless somebody goes with her."

Kiss, kiss, "would you go with her?"

Kiss, kiss, Now I have heard her talk a lot about Cindy, she is Donna's best friend. Lives two housed down from Donna. If I recall she has been divorced for about six years, I don't remember exactly how old or even if Donna said but I get the impression she is around 25 or 26.

"I don't think so Donna, she doesn't know me, heck she probably won't want to go with a stranger." I said.

She started kissing her way down my chest, teasing my nipples with her tongue. "Yes she will, I told her I would find somebody to go with her and she said okay." A little laugh "She would go with just about anybody to see Tim McGraw." Now she is running her tongue around the dark hair on my lower stomach just about to my soft cock lying pointing towards my navel.

"I don't know Donna, I think I would feel uncomfortable, I never did like blind dates." I continued

Now she was blowing warm breath on the head of my cock, all I could see was the back of her head, dark hair caressing my belly. I felt the tip of her wet tongue touch the little slit in my cock, tasting that last little drop of cum from our previous fucking. I felt the hot wet warmth of her mouth surround the head and wet lips closing tightly behind the ridge as she rolled the foreskin back with her tongue and washed the soft spongy head. Oh man it felt so good, I could feel the blood rushing back into the shaft and the head begin to swell. She felt it also and a pleased little "ummm" vibrated around my cock.

Now she had a hand around the shaft working the skin up and down, Oh yeah that's good. Now her hand is cradling my balls, pulling them up so they are in her palm and her fingers are around my cock. Feels great, now her oval lips are sliding down to meet her fingers and I feel the head against the start of her throat then in her throat as my cock is not fully hard yet. She started back up, tongue laving my shaft all the way up, by the time she got back to the head I was fully hard. She worked up and down my cock with her wet mouth till my body was screaming for release, then taking me from her mouth and jacking my saliva coated cock gently once again she asked.

"Please Jack, do me this favor, go with Cindy to the concert." and then engulfed me once more to give me exquisite pleasure. Now most women go about the getting their way thing the wrong way. Don't deny your man until he does what you want. Give him all the loving he can stand. A man can't say no to a woman that is sucking his cock so good or fucking him with that tight wet hole, that way the ladies get what they want and the men get what they want, everybody wins.

"Uhhhhhh... Okay Donna... Oh yeah use your tongue like that. I'll go... Ummmm yeah that's so good." I moaned as her bobbing head and warm little hand brought another load of cum from what I thought was a drained pair of balls. She took it all, wasn't as much this time and she had no problem with it. When my cock got soft in her mouth and it did much quicker this time, she gave one last suck on the head and moved back to lie on my chest, those big warm tits felt nice. Kissing me and grinning. "I knew you would help me out Jack."

I had to chuckle, "You know at that moment I would have agreed to just about anything. You don't play fair girl."

With a giggle she got up and went to shower before she went home, once again I followed and watched her sexy body as she did.

So here I am pulling into Cindy's driveway. The girls had planned on eating out before the concert so I hustled home showered and changed so we would have time. She must have been watching for me because I wasn't even out of the car when she came out. I met her by the front of the car. She smiled "You must be Jack." Holding out her hand she continued. "Donna has told me a lot about you, thanks for going with me."

I shook her little hand taking her in for the first time. She was about 5' 3" beautiful dark red hair that hung about halfway down her back in a long pony tail. Cute as she could be, big blue eyes and little button nose with a spray of light freckles across it. A big wide smile. I couldn't tell much about her figure since it was cold and she had a heavy coat on but I could tell she was probably slender.

"Yeah that's me." I grinned this was going to be much nicer than I anticipated, I hoped. "Donna has mentioned you a lot also but she didn't say how attractive you were."

"Oh go on, you're just trying to make me feel good." With a throaty little chuckle "but I like it."

We went to a local steakhouse and had dinner. I found she was a great conversationalist, a lot of the time with funny little sayings about whatever we were talking about or serious when we were discussing something that she though was important. I was right about her being slender, when I helped her off with her coat I saw a compact little body in a pair of tight jeans and a Tim McGraw sweatshirt. When she moved I could see that her breasts while not big were just right for her body. I was enjoying this evening very much

As we were eating desert and talking about Donna and Tim and how neither on of us could see why she married such an asshole. She looked me in the eyes, grinned and said, "I know how much you have helped her out, and she really is a different person after she visits you."

I didn't know what to say, I was stunned, what do you say to something like that. She could see the look on my face and started to laugh, she has such a big hearty laugh for such a little lady, and I had to grin despite my confusion.

"You should see the look on your face Jack." She giggled again "Donna is my best friend and you know us girls tell their best friend everything."

I was trying to regain some sort of composure, here I was enjoying Cindy's company and she tells me she knows I am fucking her best friend.

"Uh... Just what did she say about her visits?"

She had me on the ropes and she was having fun now. "Why Jack she said you eased her tensions and made her feel good."

I know my face must be bright red, I could feel the heat in my cheeks. I guess she thought she had teased me enough. She placed a soft hand on my arm and said seriously. "I think it's great that she can find some peace with somebody, she sure isn't going to find it with momma's boy. I hate to see her wound up so tight all the time, so I appreciate what you are doing." Now back to the teasing "Of course I am sure the pleasure is not all one sided."

I gave a big sigh "Okay I am completely embarrassed now, and have no idea what to say."

"How about let's go to the concert." She grinned.

"Okay, let's go to the concert." I laughed, stood and held my hand out to her, she placed hers in mine and we went to the concert. I had a great time and she seemed to also, no other mention was made of Donna and I. When I took her home I didn't want the evening to end but it was late and I wasn't certain how she actually felt about me after knowing what was going on. I walked her to her door; yes there are still gentlemen left. As she took the key and opened the door she turned, it was an awkward moment for me, I wanted to kiss her but was afraid I would be rejected, I tried to say something but didn't know what to say. That old line about well I had a great time tonight just didn't seem right even though it was very true.

"Are you going all shy on me Jack?" She said softly, then taking my head in her hands she brought it down to kiss me gently on the lips. Those were the softest lips I have ever felt, she held the kiss for a minute then let me go. She didn't turn to go in.

Finally I got enough courage to say something. "Cindy, I... well I would like to see you again... Uh, I"

She grinned "Finally, I thought I was going to have to stand out here all night, or worse yet do the asking myself, now you know that's bad for a girls ego. When would you like to see me again Jack."

I was so relived she wanted to see me again it took me a minute to gather my thoughts "How about Tuesday night, we can take in a movie if there is anything on you like, besides it's bargain night and I am a cheapskate." This got a throaty laugh.

"Okay Tuesday it is, I am glad Donna talked you into taking me tonight." She blew me a kiss and went in as I turned back to the car.

Monday Donna couldn't wait to ask how the concert went, now I know she had talked to Cindy by now and knew probably word for word what went on. I come to the conclusion that she had cooked this whole thing up, either with or without Cindy's cooperation. So I was going to have a little fun myself.

"Oh it was nice." I answered, she just stood there waiting, and I didn't say anything more.

"Well what did you think of Cindy." she asked seeing I wasn't going to be forthcoming on my own.

"Nice lady." I answered. She was getting exasperated now.

"Come on Jack I want more than that." She said seriously

I had to laugh at her expression. "Okay Donna, I am sure you have heard all about it by now, since you two seem to tell each other everything." I was pleased to see a little blush creep over her face. "Cindy is great, I am sure you know we are going out tomorrow night. So thanks for pushing me into the concert, I think you planned this whole thing." She didn't deny it just an "Oh Jack now would I do something like that."

For the next few weeks Cindy and I went out a couple of times a week. I enjoyed her company more and more and she seemed to be having a good time also, The goodnight kisses were longer and hotter and a lot of tangling of tongues but to tell you the truth I was afraid to try and go farther, the knowledge that she knew about Donna and I was holding me back, I wasn't sure what she really thought about it, she hadn't said anything more since the first night.

Finally I couldn't stand it no more, as I pulled in her drive way and stopped the car, I put a hand on her shoulder to keep her from getting out. I held her hand in mine.

"I would like for you to come out to the house Saturday, let me fix us dinner, we can have a fire, just sit and talk." I started.

She nodded "That would be nice Jack, I would love to."

A big sigh as I continued on into no mans land. "Cindy I want to make love to you. You are lovely inside and out, I don't know how you feel about me, I can only hope."

She leaned over to kiss me softly. "Once again I thought I was going to have to make the first move. I wanted it to be you wanting me. I have wanted that since the first time I saw you" I looked into those blue eyes and I could see something there I didn't think I have seen before, could it be love? She grinned and got out of the car, I walked her to the door and this kiss was hot, her lips on mine were so soft and wet, they slid around my mouth as her tongue tickled the roof of my mouth then caressed my tongue. We were both breathing heavy when she finally broke away. She could see in my eyes I wanted to go in, to make love to her. With that throaty little laugh she gently pushed my back. "Down boy, anticipation will make it all the better."

With a defeated grin I went back to my car and went home. She was probably right I was already anticipating sucking those luscious breasts and discovering the treasure she had between those slender legs.

I was more nervous the rest of that week then when Donna was coming the first time. Bill was teasing me all week about having a hot date; he knew I had been going out with Cindy and that Donna had got us together.

She arrived about 4:00 o'clock, I had a big fire going in the fireplace, and she brought a bottle of wine.

"Ahah, planning on getting me drunk and having your way with me are you, you saucy wench." I quipped

She kissed me softly, "Now Jack, you're a man, I could have my way with you anytime."

I laughed "well that's true." Now that I knew she wanted me also I wanted it to be special, not just let her come in the door and jump her bones. We went in and I got some glasses, took them in the den and sit before the fire, drank some wine and roasted some marshmallows, watched some sports on TV, yep she enjoyed sports, man what a woman. We talked and laughed and both could feel the sexual tension building, I wanted to be clear on one thing before I went any farther. I was pretty sure I was in love with Cindy and the thing with Donna had me all in a knot.

Turning to her, I took her hands in mine. "Cindy, you are on my mind constantly, I love being with you, I want us to be more than friends and lovers, heck I will just say it, I know its probably not going to sound romantic or anything, Ahh Cindy I love you."

That got a little twitch on the corner of her mouth and her eyes got a twinkle in them. "I love you too Jack."

Did she say she loved me; oh man my heart did a flip flop.

"Make love to me Jack" she whispered and drew my lips to hers. It was a soft loving kiss that grew in intensity as our desire for each other was finally going to see a completion. We were sitting on the floor before the fire with our backs against the couch and I took her in my arms and laid her on the thick rug.

I kept myself above her on my arms and just gazed at her, I loved the way the freckles ran across her nose, those sparkling blue eyes, smiling red lips, that dark red hair that catches the sun and shines.

"You got a cute nose, you know that." I said

"Why thank you sir." she grinned, "Is that what makes you love me."

"Well the fact that its part of you is a contributing factor." with a grin I kissed each eye and that cute nose before my lips found her soft compliant ones. The kiss grew more passionate, her mouth tasted sweet like strawberries. Our breathing deepened, with one hand I found a round breast, cupping it through her flannel shirt, it was a firm mound about the size of a small grapefruit, that's the closest comparison I could think of but it sure felt much better than a grapefruit. She brought her hand up to cover mine and squeeze with me as I gently kneaded and rubbed.

We continued to kiss as I started unbuttoning her shirt, then leaving her sweet mouth my lips followed the path of my fingers, kissing the flesh I exposed as I continued down her shirt, down between her breasts till her bra got in the way then below down her flat belly to the tops of her jeans. Pulling her shirt tail out of her pants I spread her shirt open, her bra was one of those flimsy front hook things and I opened it laying it back to see her pert breasts for the first time. She was watching me with a smile the whole time.

Her breasts stood proud, very little flattening, firm round mounds with a wide valley between them. Her aureole were the same shade as the rest of her breasts, just a faint outline was discernable as they were raised slightly above her skin. The nipples were raising twin little nubs about a quarter inch around that were a little pinker then her skin. Lovely, lovely mounds of pleasure. I dipped my head to take a nipple in my lips, sucking and encouraging it to come out and play.

"Ummmm darling that feels good." She sighed and placed a hand at the back of my head. I sucked and nibbled on that one a while then not wanting to play favorites I switched to the other, she had some long nipples, I had teased this one till it stood out almost a half inch. As I sucked the other one I twirled and twisted the first one with my thumb and forefinger. "Ohhh yeah baby... Ummm take more." As she arched her back to try and push more of her tender flesh into my mouth. I obliged by opening more and sucking as much of her in as I could get. I had fully a quarter of her tit in my mouth as I chewed and nibbled.

"Ohhh yeah that's the way, ummmm baby." She gasped. I was working with one hand now trying to get her jeans undone, finally I got them open and raising up I started working them down over her hips, she lifted her ass to help me, I skimmed them off to see she had on black bikini panties, just a triangle of black with a narrow waist band running around the side. I could see red hair escaping from the sides. I quickly stripped her of this last little hindrance and holding her shapely leg up I started kissing down her calf, behind her knee and up that firm muscled thigh.

My eyes were on her red furred mound as I worked my way down her leg. The hair covering her mound was lighter red then on her head, a soft curly triangle that pointed towards her pretty cunt. Her slit was just a line down between her legs, just a little nub right at the top showing where her clit was already filling with blood. I reached that treasure cave and ran my tongue down each side of those tight lips along the crease of her legs that brought a shiver from her. I was on my stomach between her legs now and placed my mouth over her nether lips, my nose nestled in her forest of fire. I was watching her blue eyes as I parted her lips with the tip of my tongue. Her eyes almost closed and I felt her hips tensing to move closer to my mouth. I slowly slid my tongue as far in as I could then curled it up and ran it along the top of her channel, I knew I had hit her G-spot when she shuddered and gave a soft little moan. I teased her with my tongue fucking it into her then up to lick her clit, then running it all the way down her slit, I had my hands now under her firm little ass and lifted her up so I could run my tongue down her ass crease and around her pink little asshole.

"Ohhhh darling that makes me hot." She gasped. I went back to work on her sweet pussy, she must use some kind of douche; she tasted of sweet honey and clean sweat. I held her ass off the floor as I made love to her tight lips, sucking, licking nibbling, kissing. Everything I could think of. She was reveling in my oral love, I could feel her ass tighten and unclench as I drove her up that ladder of passion. My face was wet and smeared now with her secretions. I could have stayed here at her sweet pussy for hours but she couldn't stand anymore and bathed my tongue with her clear cream, I swallowed every delicious drop I could get. I didn't stop I couldn't get enough of her. She finally had to push me away, her hips shuddering and shivering. Her clit so sensitive she couldn't even take my tongue on it.

"Whew baby you sure eat a girl good." She sighed as I lay with my chin nestled in her red forest sporting a cum smeared smile on my face.

"My pleasure pretty lady." I grinned.

She answered with one of her own. "Now darling let me at that big headed cock I've heard so much about."

I just shook my head on her belly and laughed. "Do you girls have to tell each other every little detail?"

"Sure, didn't you know best friends do that? Now stand up and get out of those clothes." she directed.

I complied as fast as I could, she finished taking off her shirt and bra. The fire had it nice and warm in here so we were very comfortable.

I was standing before her, my cock not soft but just beginning to fill out, it hung down just starting to raise from between my legs the hood covering all but the tip. I know it makes the head look twice as large as the shaft, I have been told that by my ex-wife, most of the women I have made love to and then Donna.

She was on her knees before me, "dang darling you could club wildcats with that thing, I thought Donna was exaggerating when she told me how big it was." She had her hand around the shaft and pulled the foreskin back to expose the head. "Ummm that looks mighty tasty" and she opened her mouth and took the head in closing her lips and humming as she laved the spongy head with her tongue. Oh man that felt so good. She had her hands on the outside of my thighs as she took most of the shaft in her tight held lips, my cock was rapidly filling with blood now and she scrapped her teeth lightly along the shaft...

She released it from her mouth and jacked it with one hand as she dipped under and took one of my balls in her mouth and rolled it with her tongue. She was watching the head be covered and uncovered by her working hand. Releasing one ball she worked on the other, the pleasure her mouth and hand were giving me had my legs quivering. I don't know why, women have sucked me off before, different techniques and all felt great but for whatever the reason her mouth felt better, hotter, her hand softer around me. It was starting to be the best blowjob I have ever had. Now she was working about half the shaft with her mouth and her hand was doing a twisting motion as she stroked the rest of it, her hot little tongue was all over the head, she was rolling my balls with her other hand, man I tell you I thought the top of my head was coming off it felt so good. I was up on the balls of my feet; the center of my body was a source of pure pleasure as she brought me to completion.

When she felt my balls tighten she pulled her mouth from me and held the head about an inch away from her open mouth, her eyes on my face. I was watching her suck me off, it was so hot to see her lips traveling up and down my cock and feeling it at the same time. I saw the first long rope of cum shoot out into her waiting mouth. "uhhhhh." I grunted. The next one followed right behind it. "ummmm" I groaned. By then she had taken the head back in and closed her lips as her little hand continued to pump the shaft, her eyes never left my face. "Ahhhh" I moaned as my balls were emptied of their white thick contents. She sucked me dry and licked the last little drop from the end of my dick.

A little smile as she licked her lips. "Good stuff Jack; you must eat a lot of vegetables, very sweet. And that look of concentration when you cum, sooo intense." She laughed.

Seeing her there on her knees before me, dark red hair falling down, some in front to fall across her breasts partially hiding them, the rest to array in a dark spray across her back, that wide smile and blue eyes. My ole dick that had begun to drop down now started back up as it filled with blood once again.

Seeing it twitching and jerking, slowly rising again before her eyes she squealed. "Oh goody, is that for me."

I had to grin; she made loving not only great but fun. "Lay down woman I have a bone I want to bury." I dropped to my knees with her and took her in my arms; we kissed hungrily, hands running all over each others bodies. I wanted her in the worst way, picking her up in my arms I turned still on my knees and placed her on the couch her firm little ass just on the edge, moving between her legs, I spread them open with my hands and then slid my hands up her smooth legs, up over her belly and palmed a luscious mound in each hand. Those hard nipples were poking into my palm as I continued rubbing in a little circular motion. I glued my mouth to her labia and tongue fucked her with abandon.

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