TITLE: Helping A Friend
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I am currently in a long-term monogamous relationship and which is a rather new experience for me. My significant relationships up till now always involved stepping out as couple or alone. I have been posting things that I have found interested and aroused me here on this page. A friend that I have on this site had asked me to relay some of my experiences so here goes one for Mary…
I had been dating Kendra for several months by this point and we were definitely at a stage of commitment but primarily to our desires. We were not sure if our relationship would blossom into something more permanent so we enjoyed the time we had together. She was a short plain little lady that barely was over five feet and chubby in an absolutely adorable sort of way. The straight brown hair that she often had in pig tails, and the fact that she was almost completely hairless, added to the illusion of her being of less than legal age. This further added to the reality of my being eighteen years her senior. It was natural that this relationship would mold itself into a little girl trying to absorb all the pleasures that an experienced partner could offer. There was an odd i****tuous overtone that she loved to play on. While it was common for her to call me “daddy” while we were in the bedroom the real fun was doing it in public. The look of shock and awe on waiters/waitresses as she would rub my leg and ask me, “Daddy can please have some wine tonight?” or “Please daddy can you get me some ice cream”. She was exploring facets of her sexual personality that she had not known existed. I allowed her a freedom to explore and supported her personal discovery. Irrespective of if she wanted to ride my cock and slap me in the face, reciting how worthless and low she thought I was, or being blindfolded and bent over the recliner so the old Chinese delivery man could use her pussy instead of giving him a tip, she wanted to experience as much as she could. The comfort we had with each other and the mutual trust allowed for a fantastic relationship. We were together for a brief period but had more experiences then some poor souls would have in a lifetime.
This particular incident occurred when I was on a road trip as part of an install team for a new conveyor system. Kendra had taken time off work to join me on the trip. Not because we were going to some wonderful location but rather because it was a small lonely town in the middle of the Canadian prairies with a population of less than a thousand and this city girl was curious to see what trouble she could find in such a remote and lonely location. I had come back to the hotel room from a day at the mine where I was working. I found her asleep in bed and her little vibrating finger toy that she used on her clit on the pillow beside her. She was enjoying a post-masturbation afternoon siesta. I kissed her awake and told here we would be going out for dinner with a work colleague. She groaned knowing that it meant a degree of conservatism was going to be required of her. “Does that mean I have to wear panties?” she asked with an obvious dissatisfaction.
After a brief ponder I pinched her nipple and told her she could wear whatever she liked. She proceeded to give me an impish look with her tired closed eyes and I felt my cock begin to engorge. I took off my coveralls and began to remove my clothes. She opened her eyes and they locked in on my erection to which she gave a little smirk. “Bring that over here”, she cooed.
“Sorry hun things are really ripe down here. I’ll have a quick shower first.” I said giving myself a few gentle strokes. Before I could step away she slithered off the bed on to her knees and began stroking my cock. She grabbed my ankle with her free hand and guided my foot onto the bed. I had that Captain Morgan pose for only a moment before I felt her nuzzle my balls with her face. I was in no shape to stop her and her tiny hand on my cock was doing wonders. I had already tilted my head back and closed my eyes when I felt her take my balls into her mouth turn by turn. She would take one in her mouth and use her tongue to give it a thorough cleaning before going to the other and then back again. Then to my dismay it ended as quickly as it begun.
She stood up and proceeded to put her tongue in my mouth. After a few moments of me tasting my ball sweat from her mouth she pulled back and said, “Let’s get this over with so we can come back and work on my gag reflex.” I gave her a quick peck on the lips and made my way to the shower. It was a running joke between us because Kendra had an awful gag reflex and couldn’t take too much into her mouth with almost nothing able to make its way into her throat.
I came out of the shower to find that regardless of the freedom I had given her to dress provocatively, Kendra had decided on simple black tights and my Winnipeg Jets jersey. On her it was ridiculously large and covered her like a jacket. There was no looking at her pert little ass and her definite camel toe was hidden from view. “Couldn’t find anything that fit you?” I joked.
“I just don’t feel like getting all dolled up. You’re ok with that aren’t you daddy?”
I cupped her chin with one hand and kissed her tightly, “Of course princess!”
We made our way to the front lobby and waited for my colleague Tom to show up. He was slightly older than me, a tad shorter and slim with a marathon runner’s physique. He actually looked a little older than his years which were a testament to the long hours he had put in to his career. He spotted us and I waved him over to the lounge. A short introduction and a shot of tequila and we went off to the restaurant. We sat on the patio enjoying the summer heat and decided to forego dinner, instead have drinks with appetizers. Kendra was busy people watching with absolutely no interest in the conversation which centered around work. She chugged down her wine and with an exaggerated sigh said, “Enough! I am going to have a pee and when I come back there won’t be another word of this engineering crap.” She grabbed my face and gave me a playful head-butt before making her way to the restroom.
Tom finished his drink and waved the waiter to bring him another. My buddy was feeling really tipsy at this point. “Thanks for not letting me stew in the hotel room. I’m trying really hard to get out of this funk but it’s just such a struggle.” Tom was currently going through a separation and his demeanor had totally changed over the last few months. What was once an easy-going and technically sharp fellow was now quick tempered and always seemed distracted at work. In our line of work that type of carelessness meant the danger of electrocution so I had specific instructions by management to keep him in check.
“No worries! You need a distraction and you know I’m always here for you.”
Tom took the glass from the waiter and took a swig and set it down. Keeping his eyes in the glass he quietly asked if we were in room 219. I looked at him with an amused smile knowing where this was going and answered yes. “I thought I recognized your friend’s voice. Sounded like you were torturing a cat when I walked by there last night.” I distinctly remember the “cat” comment as I wasn’t exactly sure how he came up with this. I was using Kendra’s back door the previous night, and she was subjected to about forty-five minutes of vigorous ass fucking. She was very vocal with her shrill voice while I was rather merciless with my sodomy. It was obvious that my little trooper was playing through her discomfort until she got accustomed to the intrusion. I came twice in her ass and it really was a sad sight by the time I was done. Her poor little rosebud was open and loose and her ass and thighs were red all over from wherever my hand landed while spanking her. I remember her cuddling into me, sucking on my nipple and saying “That wasn’t very nice daddy.” just before she drifted off to sleep.
“Ha! Yeah she doesn’t like to hold back”, I chimed.
“God, it’s been months since I’ve cum in anything other than my hand.”
“Maybe you should rent something for an hour or so?” Regrettably that was the best suggestion I could come up with.
“With what? Good looks and charm? I have neither of those as well no money. You know what this separation is costing me.”
The conversation ended there as Kendra returned. “Are we still talking about work? If you are, there are some construction workers over there that I’m going to hang out with.”
“No, no, no we’re done” laughed Tom.
It was good to see him laugh. He really was struggling with things. “No princess we were just talking about how you could help Tom out.” I had made the decision brash and quickly but decided to see where it would go.
“Me? How?” there was that impish grin with a tilted head.
“Tom’s going through a real tough time and he could use a real stress relief so I said there would be nothing better for stress then good sex. So guess what we need you to do?”
It took a moment for it to sink in for all the players. Tom suddenly over exaggerated a nervous laugh into his drink. Kendra looked at me with pleading eyes and disbelief. “No please. Really daddy?”
I rubbed her cheek and said “Princess it would be really nice of you.” We just stared at each other for a moment until she lowered her gaze. I actually forgot that Tom was there and looking at me wide-eyed. “We should get going.”
I put my arm around Kendra’s waist and held her close as we made our way to the car. I sat her in the back and Tom took the passenger seat up front which incidentally was opposite to how we drove down to the restaurant earlier. It was a silent ride back to the hotel as Tom tried to make some nonsensical comment about the weather and Kendra looked out the window but stealing sideways glances at me through the rearview mirror. Any doubts I had immediately disappeared when I seen her mouth curl up into a smile. It was brief before she regained her composure but it told me all I needed to know. We climbed the stairs to our room and as I fumbled with the keycard Tom said, “Well goodnight guys.”
“You’re not going anywhere.” I stated.
“Listen, Rob she doesn’t want to. It’s OK. I’ll be OK.”
“My princess knows how important this is. Come on, get in here.” I opened the door and walked in followed by Kendra. It took him a moment to get his feet moving but Tom got his hand in just as the door was going to close shut.
He stood at the doorway unsure of the next move. I had taken my shoes and socks off and lay down on the bed. No one moved and I said nothing. I let it hang in the air for a moment. Kendra acted as if she was unsure of what to do with just a twinkle in her eye as she played the part of innocent little girl. Reality was that innocent girl still had red welts on her thighs and bum from the night before. I could see the tent start to form Tom’s pants. Then I mercifully spoke, “Take off your clothes Kendra.” She hesitantly removed the jersey. Then she peeled herself out of the tights. Tom tried to step forward to help when she was struggling and almost went off balance. “Stay right there.” I said to him. Now with just a bra and a G-string on she looked as if pleading to me and back to Tom. I waved her to my side of the bed and had her sit on the edge of the bed. I grabbed hair tightly and kissed her. Our tongues began to wrestle and explore each other’s mouth. I let go her hair and undid her bra. Her puffy nipples came to view.
“Your turn Tom.” There was no apprehension on his part and he was naked in a flash except, almost comically, for his socks. His cock was long and thin. Kendra broke her kiss from me to look at his tool before she looked back at me and gave a wide smile without letting Tom see. He had an uncut head but the skin was pulled back and it was oozing precum. I waved Tom to come close. He was quickly beside me and I could see his cock urgently sticking straight out and it seemed to be just over eight inches. Unfortunate about his lack of thickness though. Nonetheless I almost wanted to see how much I could fit down my throat but stopped myself unsure if that would have freaked out Tom. I broke my kiss with Kendra and nudged her forward. She looked up at Tom and tentatively grabbed the base of his cock. He let out an audible sigh. Her gentle strokes were greeted with a subtle rocking motion from his hips. He put a hand on her shoulder to steady himself. Kendra reached back with her free hand and began massaging Tom’s cute little tight bum cheeks. I really don’t think Tom was prepared when in one motion she pulled his ass cheeks forward and engulfed his cockhead in her mouth. A groan of satisfaction escaped Tom’s lips as he stood transfixed with his eyes closed. I could tell Kendra was using her magical tongue all over his cockhead. Then she began a slow motion of taking a bit more of his cock into her mouth and then pulling back. This was again met by a gentle forward thrust by Tom’s hips. Tom was using both hands now rubbing her shoulders. There really wasn’t any slow build up to what came next. It was sudden and there was really no stopping it. Tom had been standing there with his eyes closed tightly and gently rocking back and forth into Kendra’s mouth for a few moments when he very quietly whispers something almost inaudible. I had an idea of what he had said but I made him repeat it. “What do you want?”
“I want to fuck her face.” He said a little more clearly. The gravity of this request was not lost on Kendra as she realized what this may actually entail as she had a full appreciation of Tom’s instrument which was currently in her mouth as far as she could comfortably take it. I threw a pillow on the ground and pushed Kendra off the bed. She never lost her rhythm and kept Tom’s cock in her mouth as she got to her knees on the pillow.
“Tell me again Tom.”
He suddenly opened his eyes and looked right at Kendra and said “I’m gonna fuck this girl’s face.”
I responded with, “I don’t think she believes you.” Kendra pulled of Tom’s cock to say something to me. It was a split second in time that I photographed in my mind. Kendra turning to say something to me with her chin connected to Tom’s cock by a long thin string of spit. It was only a split second and neither Kendra nor I was prepared for the next instance when Tom grabbed a handful Kendra’s hair in one hand and used his other hand to tightly grip his cock as he shoved it deep into her mouth. He very quickly moved to the standard face fucking pose with his feet open, knees bent, and each hand having a tight grip of Kendra’s hair making sure she could go nowhere. His hips were no longer doing a gentle rocking motion, but rather it was obvious whenever his cock hit the back of her throat as his urgent trust would come to a dead stop. She had her hands on his hips and was trying to push back as best she could but to no avail. He was desperate and her face was his salvation. He attacked her face trying to shove his hips as far forward as he could before slamming to an abrupt stop. Kendra made a series of pleading noises as she breathed out her nostrils that were completely incoherent as she struggled against his urgent thrusting cock. He eventually fucked her so hard it pushed her out of the kneeling position and in a very undignified fashion pinned her head on the bed and continued to fuck her mouth. I could see her mascara run down her face with her tears and the continuous gagging was music to listen to. Tom was now doubled over with his face on the bed, actually resting his forehead on my foot, and making a guttural sound as his primal passion over took him. He was so far gone that at one point he was actually sucking on my toes. Mercifully the assault was reaching its crescendo. Since he was slamming his hips for all he was worth for some time now, the giveaway that Tom was going to shoot came when he started to shriek, “Eat my cum bitch!” I jumped up and got behind Tom and pulled his hips back pulling his cock from Kendra’s mouth. I gripped his cock tightly and my hand was a blur as I jerked his organ. He remained doubled over and exploded all over Kendra’s neck and breasts. I could hear her wheezing breath and felt her wet tears on Tom’s groin.
I had just finished milking the last bit of cum from his cock that he no sooner turned almost running from my grip and dressed. He never looked up at me or at Kendra. He was gone so quickly it left no time for contemplation of what just occurred. I look down at Kendra who was still holding her breasts up. You could easily see where Tom had a death grip on the hair on her head. Her tears were still fresh and gleaming. I got a warm wet towel from the bathroom and wiped her face. After a few gentle kisses she opened her mouth and I could clearly taste Tom’s cock as I sucked on her tongue. I stroked her hair gentle and kissed her eyelids. “You didn’t think I could do it did you?” she asked.
“No, princess, I didn’t.”
“Were you impressed?”
“Immensely, sweetheart.”
She suddenly beamed a satisfied grin. She looked me dead in the eye, raised up her cum covered breasts, and said in her best chipmunk voice, “Look what I have for you!”
I chuckled and began to clean up Tom’s cum from her breasts with my tongue. Lapping most of it up but feeding her from my mouth every so often.
We had just cleaned up and were cuddling ready for sleep when I received a text from Tom. “Thank you both” with a happy face emoji. I gently rubbed her rectum and I whispered to her, “Maybe you want to go give him something to help him sleep?” She quickly opened one eye and cast a hateful glance in my direction.