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The Chaperons €“ Part I

“Please mom, please, the coach said if we didn’t get one more chaperon that we wouldn’t be able to go. Can you do it; please it would really make the guys on the team like me. I would be kind of a hero.” Her son pleaded with Jennifer Porter. He was on the high school football team and because of their success of recent years, they had been scheduled by a top team on the other side of the state, which meant a long ten hour ride on the team bus and two over nights…one on Thursday before the Friday night game and then Friday night.

“Well, let me call your dad and see if he is okay with it and if he can take care of your sister.” I relented.

“Oh mom, thank you, thank you.” Tommy hugged his mother, “You’re the greatest.”

After a short conversation with her husband she went into Tommy’s room and gave him the good news. She agreed to help chaperon the football team on the road trip. ‘What have I gotten myself into?’ she thought as her son hugged her again.

A few days later it was Thursday morning and everyone was gathering near the two school buses that were designated to take the team across state for the game. With all the parents around say their good byes she wasn’t sure who the other chaperons were. Finally, a coach came up to her, asked if she was Mrs. Porter and told her to which bus she was assigned. Her suitcase was loaded onto the team’s equipment trailer and everyone was told to load up. She ended up on the bus with all the coaches and was the lone woman on the bus. ‘Thank goodness I brought a book to read.’ She thought, as the coaches immediately gathered around in two rows of seats just behind her front seat. One of the coaches eventually told her that because they were on this bus the rest of the chaperons were put on the other bus. This did relieve her mind some, as she was beginning to think she was the only one.

Jennifer finally got to meet the other chaperons when the buses stopped for the lunch break. They all gathered at one table and introduced themselves. Besides Jennifer there were two white guys, Ed Holden, the produce manager at a Safeway and Jim Crocker, a car salesman at the Ford dealership; Juan Gonzales, a Hispanic working in construction; and Joe Monroe a black man working at the hospital. Jennifer shared that she was a housewife and her husband was an insurance agent. Following the introductions, she thought to herself, ‘Crap, I am the only woman. I wish I knew this before I let Tommy talk me into chaperoning.’

The rest of the bus ride was uneventful and they finally got to the hotel. Everyone was assigned rooms and the chaperons were spread out on the various floors where players were assigned. Following dinner Jim told Jennifer that the other chaperons were meeting in his room about 10:30 after lights out for the kids and she was welcome to stop by. She thanked him and went on to her room not thinking much more about it.

After performing her chaperon duties and making sure everyone was in their room and preparing for bed Jennifer went back to her room, sat in the one chair and relaxed. She glanced at the clock and saw that it was 10:20 and remembered the invitation. ‘What the hell,’ she thought, ‘I don’t want to seem antisocial.’ She wanted to get out of the sweatshirt and jeans she had, had on all day so she decided to go…she stripped, hopped into the shower, dried off and decided to wear the one skirt and blouse she had brought. It wasn’t a short, short skirt, but was a full skirt that came to about three inches above the knee. The blouse was a white silky type that “Ved” in the front with buttons starting between her breasts. To keep from showing her bra she wore a half cup bra that was lacy and had an under wire to help hold up her 34c cups. She looked in the mirror and thought, ‘Not bad for a 38 year old woman. She had managed to keep her hips from spreading and to keep her “girlish’ figure by jogging and doing other exercises on a regular basis. Pleased with herself, she left the room at about 10:45.

As she reached Jim’s room she had second thoughts, dismissed them and knocked on the door. Jim opened the door and with a big smile and that car salesman’s charm welcomed her to the ‘party.’ Everyone was there and said hello again. Ed was already sitting in the lone chair so when Jim offered her a beer, she took it and sat on the edge of the bed. Jennifer had already told everyone to call her Jenny. They chatted about how the team was doing and what their chances were in this big game, etc. And then somewhere along the line and no one knows how and when for sure, they started telling jokes. Everyone was laughing and Jennifer even told a couple. It wasn’t long before someone told an off color joke, which was really funny. Well, that one lead to another and another and Jennifer remembered one her husband always told and shared it with the group. They all laughed and kind of looked at her more as one of the guys after that.

Then Juan told one about cock sucking that cracked everyone up. When, out of the blue, Jim said nonchalantly, “Do you like to suck cock Jenny?” The room went silent and Jennifer could feel everyone’s eyes on her. You could cut the tension with a knife. Rapidly trying to think what to say she blurted out, “Sure, doesn’t everyone.” Maybe that came from how relaxed she had become with the guys or maybe because she was halfway through her second beer, which she seldom drank. Then everyone broke out into laughter as the tension eased.

However, Ed, the produce manager, got up and came over in front of Jennifer and looking down at her sitting on the edge of the bed said, “Do you really, do you really like sucking cock?” Before she could answer he continued, “My wife won’t do it…I have never had my cock sucked, never. Will you do it, please will you?” She looked up at him and the look on his face told her that this wasn’t just a line that he was indeed pleading with her. She even saw his eyes start to water over.

Everyone was silent then Jim said, “Do it for him, every guy should have his cock sucked at least once.” She couldn’t believe what was happening, what should she do, her mind was racing a mile a minute when Ed unzipped his fly, reached into his pants and pulled out his penis. It was uncut and three quarters hooded. Holding it between his thumb and index finger it hung there semi-hard. When Jennifer looked down at it, it almost looked sadder than Ed’s eyes. “Come on Jenny do it” Jim continued to encourage.

Then the other two joined in, “Be a good sport, Jenny” Juan said.

“Do it, we wont tell anyone it will stay in this room…right guys?” Joe added. They all nodded and mumbled their agreement.

She looked back at that sad little penis in front of her. “Please.” Ed pleaded. She reached out and cupped it in her hand, as Ed released it to her. Just the touch of a strange cock in her hand was somehow electrifying. She looked around at the others and they were all mouthing, ‘Do it.’ to her. She looked back at Ed’s penis that was slowly growing in the palm of her hand. Then, as if in a daze, she slipped from the bed down to her knees, leaned forward and took Ed’s cock into her mouth. In that it was still in a semi-hard stage she was able to take it all without any difficulty and start sucking on it.

Ed immediately started moaning and his cock started coming to full attention. Her tongue ran over the tip, which seemed extra smooth compared to her husbands cut cock. However, as Ed had a little belly on him her nose kept hitting his belt buckle. Jennifer pulled back to kiss the tip and at the same time unbuckled his belt and pulled his pants down. It looked funny to her to see his cock sticking out of his briefs so she broke from his penis and pulled his briefs down to his ankles with his pants. She thought, ‘Well, I have already done this now, I might as well make it something he will never forget.’

Jennifer took a hold of his cock at the base and started licking that smooth head now oozing precum and hard as rock. She licked all around the head, kissing it occasionally then licking up and down the sides until she lowered her head under his cock and sucked in his ball sack. She could feel one then two balls as she sucked them into her mouth. She let them ease out of her mouth and licked and kissed his scrotum some more before moving back up his cock to take in once more into her mouth.

As she started sucking harder and moving her mouth up and down his shaft all the others had gathered around to watch a couple of them were feeling their own cock through their pants while the third had his out and was lightly stroking it. Meanwhile, Ed had his eyes closed was moaning and saying undistinguishable words, as his knees were ready to buckle from the ecstasy he had never before received. Jennifer was no longer aware of the others in the room. She was sucking a cock, a man’s cock that she had only met today. It was different than her husband’s in both the taste and feel of it. As with Ed, Jennifer’s eyes were now closed and she was sucking and swirling her tongue around his cock. Her head was bobbing faster and faster. Then Ed let out a huge groan, pushed against Jennifer’s face and shot a wad of cum into her mouth.

Jennifer had felt him tighten and knew it was coming, but she wanted to make this a totally awesome experience for Ed. If she was going to suck a stranger’s cock for him for his very first time to receive a blow job then she was not going to deprive him the experience of cumming in a woman’s mouth. Besides, she was kind of curious how his cum would taste compared to her husbands. As he sent his seed into her mouth she thought that it tasted a little sweeter than her husband.

Everyone in the room could tell that he was shooting his stuff in her mouth and various sounds came from them such as, “Oh shit.” “God do it.” “Fuck her mouth.” “Fill’er up.” “You dog.”

Jennifer eased back on Ed’s cock to swallow what he had deposited. Ed, thinking she was finished with him pulled out of her mouth and then, unintentionally, shot a last couple of streams of cum onto her face. He looked down at her almost in disbelief at what he had done, as his cum started running down her face. He dropped to his knees in front of her apologizing, “I am so sorry, I didn’t mean too.” As he tried to wipe it off with his fingers, but only managed to spread it around more.

Then he kissed her cheek and said, “Oh Jenny, thank you, thank you, thank you that was the greatest thing that has ever happened to me. You are the greatest, kindest, most gracious person in the world.” And with that he leaned forward and kissed her on the cheek again muttering, “Thank you.” She leaned back, took his face in her hands, looked into his eyes, smiled and mouthed, ‘Your welcome’ and kissed him on the lips.

Jennifer leaned back on the side of the bed as Ed struggled to his feet and stepped away revealing Jim, completely naked with his stiff cock sticking out in front of him said, “Jenny, can I be next? That was so awesome I have never seen anything as sexy as that in my life. You don’t have to, I won’t force you, I just want to be part of something special. I should have asked before getting naked I am sorry. Now I know you won’t do it. I’m such a klutz.” She looked up at his cock, again like Ed’s it was so much different than her husbands, who was about six and a half inches long and just stuck out straight. Jim’s was long, somewhere between eight and nine inches and slim with a sweeping curve upwards.

Jennifer rose back up to her knees, stuck out her arms in a beckoning manner, as Jim moved up to her and felt her push his cock up and her tongue start to slide up and down his cock’s sensitive underside.

To Be Continued

End of Story