The Lacrosse Team Chapter 8: The Jenny Treatment [m21/f40s] [teasing] [age gap] [cowgirl] [oral] [multiple orgasms] [long]
Chapter 7: The Group Project
As I got ready and walked out of my apartment door on Saturday, I was filled with a new degree of excitement. Today I would be traveling with the team to Notre Dame for our next game and tonight I would be sharing a room with Jenny, one of the assistant coaches. Savannah told us that she had used a random name generator app on her phone and it chose her to be my roommate for trip.
Despite that excitement, anxiety also constricted my chest. This was an entirely new ball game. I wasn’t sure what the expectations were following our agreement earlier in the week. What are we going to say to each other on the trip there? Is it going to be awkward. Would all the coaches still go out as a group? Would Jenny and I do our own thing? How far did she want to take things?
As I walked to meet the team bus, I had many questions and few answers.
Once I joined the team outside the athletic center to wait for our ride, I saw Jenny make a beeline for me. At least that took the guessing out of whether she wanted to talk to me before tonight.
“Good morning!” she said cheerfully as she waved me away from the group. “I have to say, I’m quite excited for tonight.”
“Me too!” I agreed. “What are you thinking we should do?” I asked, hoping not to betray my stress.
“Well, I was imagining being in your shoes. If I were you, I’d be a bit unsure what to expect.”
“You’ve got me pinned,” I replied with a smile, glad that she already knew how I was feeling.
“So my first question is do you want me to be in charge of our plans? Or do you want to be in control?”
“If given the option, I’d love it for you to be in charge,” I answered honestly.
“Ok. Any boundaries you want to make sure we don’t cross?”
“None that we haven’t already talked about.”
“Excellent. Here’s what I’m thinking then. I put us together on today’s flight. All day, I’d like for you to tease me: A little grab here. A sneaky kiss there. Things like that.”
“Oh I already like the sound of this.”
“Then, after team dinner tonight I think we should go have a couple drinks with the girls, then back to our room for fun. Sound like a plan?”
“Definitely. I love that,” I replied. I glanced over at the team to make sure no one was looking and gave Jenny’s ass a quick squeeze.
“Oooh,” she yipped. “Yes, just like that,” she said with a devilish grin.
*******
It had been a long day by the time we got through our team dinner. I was grateful that Jenny let the other coaches in on the plan. Hopefully that would cut down on some of the teasing or questions from them.
Jenny and I had enjoyed subtly touching each other and teasing on our flight over—I was basically hard the entire time. And I had appreciated getting to know her better. She was originally from California and had moved to the east coast to play college lacrosse. Since then, she had coached with a few different staffs until landing here while Savannah was still playing in undergrad. She said she had known that Sav was a born leader even back then and was grateful to coach under her now, even though she was quite a bit younger.
Jenny told me that she had once been married for a year when she was younger, but it just wasn’t a good fit. Since then, she’d had a couple of serious partners but mostly enjoyed playing the field. She also mentioned that she was bi-sexual and enjoyed being with men and women equally, though often for different reasons, which gave me a lot to think about as we prepared for landing.
Our game was a nail-biter. There were probably half a dozen lead changes in the last five minutes and we eked out win when we scored with only 20 seconds left. It was, by far, the closest match since I started helping out the team, which meant that everyone’s nerves were a bit fried by the end. It was cool to see Savannah in action making changes to her game plan as needed and adjusting on the fly. Once again, I was beyond impressed by her mind for the game.
At dinner, we picked a nearby bar within walking distance to go to for a couple drinks. The other ladies decided that they weren’t going to go dancing or anything so we didn’t need to change out of our casual clothes.
As we sat around a high-top table finishing our second round, Brit finally lost control of her mouth: “So, you guys gonna fuck each other’s brains out tonight? God I’m so fucking jealous!” I felt my face turn red in a hurry.
“Brit! We agreed we weren’t going to bring it up!” Erin chided.
“You knew I couldn’t keep that promise. And honestly, I’m proud of myself for holding off for this long.”
“It’s fine. She can ask. Doesn’t mean we’re going to tell her anything!” Jenny retorted.
“Oh c’mon. I’m sure you’ll crack eventually. I hope you’ve been using your XL dildos this week, otherwise tonight is gonna fucking hurt with his monster cock.”
“You’re too much,” Savannah said simply.
“Oh please. Have the rest of you not also been at home every night pounding your own pussies thinking of his dick?”
“Brit, shut the fuck up,” I ordered, hoping to end this conversation.
Erin, Jenny, and Savannah all busted up laughing while Brit just dropped her jaw in shock.
“Well, well, well, look who found a voice,” Jenny said, sounding impressed and tossing back the rest of her drink. “I think that’s our cue. Ready to head back?” she asked me with an eyebrow raise.
I nodded and finished off the rest of my own beer. Standing up, I held out my hand to her. She took it with a smile and said “Night, ladies,” as we began to walk off.
“Hope you can’t walk tomorrow!” Brit called after us. Jenny silently gave her the one finger salute as we continued our exit.
As soon as we got outside the bar, I grabbed her by the waist and pulled her in for a kiss. All day I had been trying to get a read on what she was looking for: Tender, gentle seduction? Raw feral physicality? Being in control? Being controlled?
Despite observing and thinking about this all day, I still didn’t have a clue. So, I decided to just go with what felt natural for me and hoped that she was be receptive to the authenticity. For now, I wanted to kiss her.
And she wanted to kiss me back.
She met my mouth and tongue in a violent game of twister in the alleyway outside as her hands slid up under my shirt and explored. My hands cradled her chin and neck as I tasted the salty sweetness of the margarita she had just finished—it was delightful. Her hands continued to roam as one came around my abdomen and toyed with the waistband of my jeans.
“Are you hard for me, yet?” she whispered in my ear.
“Why don’t you find out?” I asked as one of my hands slid down her back and gave her ass a squeeze through her leggings.
At this, she simultaneously pounced back on my mouth as her hand dove into my pants, where she learned that I was, indeed, hard for her.
“Oh, fuck. We gotta get back to the hotel,” she panted as she wrapped her fingertips around my girth. I grabbed her hand and began marching us back towards the hotel, grateful it wasn’t far.
The door to the elevator closed behind us and we were on each other again immediately. As our mouths met again, her hand was grabbing at my dick through my pants while I squeezed at both of her ass cheeks. When the elevator dinged and the door opened at our floor, she grabbed my hand and literally began running down the hallway towards our room.
After fumbling with our keycard and pushing through the door, Jenny shoved me back onto the bed and climbed on top of me. Our lips re-attached as she straddled me and started grinding her crotch on mine.
“I originally wanted to take things slow,” she gasped in between kisses. “But now I just NEED you inside me. Can we circle back to the foreplay later?”
“Fuck yes,” I said excitedly. She lifted herself up off me and stood up next to the bed as she grabbed at the hem of her shirt, lifting both it and her bra underneath off entirely.
I had seen her tits earlier that week when I came on them, but everything happened so fast that I hadn’t really had the opportunity to take them in. They were perfectly suited to her athletic body. Not too big, but plenty of weight for them to be tantalizing. I couldn’t wait to play with them.
Then, she reached for the waistband of her stretchy leggings and pulled down, revealing a sexy lacy thong that I imagined she had picked out specially for tonight. As she began pulling these off, a long strand of grool remained connected to her pussy until she had gotten them to her knees.
“These are completely soaked through. You’ve had me so fucking wet today,” she said as she kicked them away.
I finally had the chance to take her in fully, and she was magnificent. Wavy brown hair topped a tanned athletic figure that she clearly spent significant time maintaining. Her lovely tits led down a tight abdomen to a patch of well-manicured pubic hair, below which I could see a pair of meaty inner lips. A muscular ass topped long, toned legs. Although there were signs of age here and there, I couldn’t wait to explore that body further.
“I’m glad you seem to like what you see, but I really need you to get undressed now,” she requested, pulling me from my reverie.
“Oh, yeah, sorry!” I replied quickly, popping up and beginning to undress. As I yanked my boxers off last, I asked, “Should I grab a condom?” I had brought some in my bag, but wasn’t sure what the plan would be.
“Oh you don’t have to worry about that, hon. I’ve been taken care of for a long time. And by the time we’re done, I want to feel coated in your cum inside and out. Now lie back on that bed,” she instructed while pulling back the comforter and sheets. Jenny generally seemed self-assured, but I had certainly not seen her this confidently dominant, even in her role as a coach. It was hot as fuck.
I followed her orders and she was quickly back on top of me. She pinned my cock up against my stomach as she slid her sopping pussy up and down along it’s length. Even that felt good.
She looked me in the eyes, and said, “Brit was right. I’ve been using my biggest dildo all week thinking of you. I probably came ten times in the last four days thinking of this moment,” she admitted. “And I can’t believe I’m the first one of us that actually gets to ride it. Those bitches can’t stop telling me how jealous they are.”
To hear how much she had been thinking of me and how much they all had been talking about me turned me on even more. I couldn’t wait to be inside Jenny as I looked up at her beautiful tits and body.
“You ready for me to ‘fuck your brains out’ to put it in Brit’s crass words?” she asked as she lifted her hips up and grabbed my shaft.
“So fucking ready,” I replied excitedly as I felt her guide my tip to her drenched hole.
She simply grinned as she aggressively dropped her weight down onto me. Most women I had been with needed some easing in, but not Jenny. She was quite ready.
“Fuuuuuuuuuck! That feels even better than I had imagined!” she groaned as she threw her head back in pleasure.
Her pussy felt amazing for me, too. Although not quite as tight as others had been, it still felt like a perfect grip on my cock all the way from the base up to the head.
She leaned back and balanced her hands on my thighs, her feet firmly planted on the bed next to my hips as she quickly began bouncing on my dick. Somehow, each time she dropped down it felt better than the one previous, and every time she slid herself back up to my tip, the suction of her lips made me moan in pleasure.
I reached up and started playing with her clit using my thumb, her leaned-back posture giving me perfect access. So far, she had been on the quieter end, with small whimpers here and there, but now she began to moan in earnest with the new sensation.
“Fuck!” she panted. “Wait, I don’t want to come yet. Flip, me over,” she requested as she slid off of me.
She quickly turned around and got on her hands and knees, presenting her ass up to me. I tipped forward onto my knees and wiggled my head up along her slit and her clit. “Just put it in! Please!” she begged.
Needing no further invitation, I plunged my dick deep into her pussy. “Ohhhhhhhhhh,” she moaned as I bottomed out. My balls rested up against her clit. “You’re gonna make me come so hard like this.”
I grabbed her hips while guiding my cock back out of her wet hole, and then slammed my length back into her, eliciting another loud moan. Again, and again, and again I pounded my cock into her pussy as I could feel her orgasm (and mine) growing closer with each progressive thrust. After a couple dozen more of these, I knew she was at her limit as her moans became unceasing.
Finally, it hit her.
“Fuckinngggggg shittttttt,” she wailed as her arms collapsed from under her and her face slammed into the pillows, which barely helped to deaden the sounds she was making. I felt her pussy contracting and relaxing in turns around my cock as her legs shook. From my point of view I could even see her anus pulsing from the waves of her climax. I watched her back heave with her quick breaths as the intensity of her orgasm continued to flow through her.
This went on for a few minutes until she eventually slid off my cock entirely and rolled onto her back, her curly hair splayed all over the pillows underneath her. Still panting a little, she looked up at me and softly said, “That was insane. Holy fuck.”
“Yeah, that was incredible,”I agreed.
“Ready to finish the job?” she asked me with a smile. Spreading her legs for me, she added, “I still need to feel that cum inside me.”
I just grinned and propped myself back up on my knees, guiding my cock back to her entrance.
I rubbed my tip along her slit and pushed, plunging back in with my whole length. “Fuck me! Hard!” she requested.
“Absolutely!” I replied. I grabbed her thighs and lifted her ass off the bed so that I could get a bit better leverage, and began pounding my cock into her. Going so hard felt good to me, and with each stroke I was taken closer and closer to my own climax.
Soon enough, I was right on the edge. “Oh fuck. I’m gonna commmmmmme,” I moaned as I continued hammering away.
“Fill me up, Andy!” Jenny demanded.
That did it. I slammed into her one more time as deep as I could go, and in an instant, I felt my cock begin to throb as I unloaded into her, my muscles tensing with the overwhelming sensation of my orgasm. “Fuuuuuck,” I groaned as my dick emptied and I fell on top of her, our mouths connecting in another passionate kiss.
I pulled out and watched as my cum leaked from her slit.
“Tonight has already been wonderful, and we’ve only just started,” Jenny said warmly as I lay down next to her and kissed her again. Light kisses quickly turned to making out and then I started to explore.
I kissed down her neck and collar bone until I finally was able to get adequately acquainted with her boobs. They felt even better than they looked. I licked her nipples and massaged each breast. “Oooh, that feels nice,” she cooed as I let my mouth casually wander and eventually return back to her hers.
My hand slipped down her abdomen until it found her pussy again, sticky with cum. I caressed her lips and her clit softly and without urgency. We had plenty of time and no hurry.
“Looking to finish what you started the other night?” she teased. Her fingers traced around my pecs and encircled each of my abs as they slithered down towards my cock.
“Oh, very much,” I replied with a matching tone as I started exploring her vagina, her inner thigh, her vulva. Slowly, I homed in on her clit with increasing intentionality. “Yes. That feels goodddd,” she purred as she wrapped her hand around my shaft and began sliding it up and down.
With each passing minute, her whimpers of pleasure grew, eventually turning into moans. Soon enough, her hand was wildly rubbing my cock as her body spasmed from one position into another like she was being shocked.
“Yes. Yes. Yes!” she chanted as I maintained my rhythm and motion, despite her wild movement.
“Yes! YES! YES!” she screamed as her second orgasm of the night overcame her. This time, instead of shaking and collapsing, her muscles tensed and her legs clamped around my hand. “YESSSS!” she howled, no longer caring if any of the surrounding hotel rooms could hear us. I thought for a moment about Savannah and Erin one room over and two of the players on the other side of us. If any of them were back in their rooms, they would surely be hearing Jenny quite clearly.
As she came, her mouth re-attached to mine as she kissed me as if she was trying to devour my tongue. My fingers started to go numb from the pressure pinning them between her thighs.
“Good god, you’re good at that,” she said once she started to come down and release. ”Brit’s right. If you’re not in one of our player’s beds every night, it’s a damn shame. Waste of good talent, honestly.” She chuckled and I laughed along with her.
“Now it’s your turn,” she said with a devilish grin. “But first, I have a confession to make.”
“Oh really? I love a good secret,” I replied with a conspiring look as she shimmied her way down towards the foot of the bed in between my legs.
“When you came all over my chest the other night, and I went to the bathroom to clean up, I tasted some. It was goddamn delicious. Tonight, we’re not wasting a drop of that tasty elixir.” She was also not wasting any time as she wrapped her lips around my head and quickly took in as much length as she could.
Her experience was apparent as she made me feel things I’d never felt from a blowjob before. I momentarily considered how much money she could make doing an online masterclass on her technique. It was just that good.
It didn’t take long before she had me on the edge once again. “Holy fuck that feels good!” I whined as she took me into the back of her throat while expertly fondling my balls.
“Oh Jenny. I’m gonna come. Are you ready?” I panted. Her eyes met mine and she nodded as much as her current position would allow.
Immediately I felt my own next orgasm hit and my second load of the night was discharging into Jenny, though this time into the back of her throat as she kept nearly my full length in her mouth the whole time.
Her eyes watered, but she remained true to her word—not a drop escaped her lips. When my cock finished unloading and my climax ebbed away, she released me from her. She swallowed one more time and then opened her mouth wide, sticking out her tongue.
“Told you I wouldn’t waste any! And honestly I could guzzle that all night,” she said proudly as she cuddled up into my arms and pulled the sheets up over us. I leaned over to kiss her again as I recognized a feeling of calm contentment.
She quietly lay in my arms as we enjoyed the aftershocks of our pleasure and appreciated the feeling of our naked bodies intertwined.
After some time, she spoke up: “You know, I was trying to remember the last time I came that hard from someone’s penis…”
“And?…”
“I honestly can’t remember. Certainly not in the last ten years. And I’m not sure about before that. Definitely not with my husband. I honestly can’t recall.” She giggled as kissed me again. “I think I might go shower, care to join me?” she asked, starting to get up from the bed.
“Absolutely,” I grinned as I followed her.
In the shower, our hands were continuously groping, “washing,” and playing with each other. My cock stayed hard as she rubbed her body against me and teased me until our skin was so wrinkly that we had to get out.
As we dried off, I asked, “You ready to get to sleep, or think you’ve got one more orgasm in you?”
“Oh I’ve got AT LEAST one more orgasm in me. I can sleep on the plane,” she replied as she fell back into the bed.
“That’s what I was hoping. Can I use my tongue this time?”
“I’d be insane to say ‘no’ to that,” she answered with a wide smile as she lay on her back and spread her legs.
I teased her a little before diving in, taking little nibbles on the insides of her thighs and letting my tongue explore her whole pubic area. Although not obvious, there was a faint trace of my cum still present, but it didn’t bother me as I stuck my tongue in her slit and then licked up to her clit.
This quickly elicited a moan and her hands reached down to the top of my head, messing with my wet hair and pushing me into her crotch. I thought that with it being her third time around that this time might take a little bit longer, but the opposite happened. Much faster than I anticipated, her breathing quickened and she started panting. The moans followed quickly as she writhed underneath me. With each progressive orgasm she seemed to be getting more sensitive.
“Oh Andyyyyyyyy,” she groaned as she lifted her hips into my face and pushed on the back of my head. “YESSSSSSS,” she moaned as I felt her pussy begin to spasm for yet another time tonight. Like the last time, her legs clamped around my head, holding me in place as I continued pleasuring her until she had to shove me away due to the overwhelming intensity.
This orgasm burned bright, hot, and quick as she continued squirming, but sooner than before she was already regulating and returning her breath to normal.
She looked up at me with adoring eyes as she whispered, “I’ve only ever come three times in one night once before in my life. That was incredible.”
“I live to serve,” I replied, leaning down to kiss her again.
“Well why don’t you serve me another round of that dick,” she instructed with a smirk as she looked down to my engorged cock. She lifted her left leg into a glider position, spreading her soggy pussy lips for me again.
“Yes, ma’am,” I teased submissively as I straddled her right leg. I used my tip to toy with her clit and lips, wanting her to beg for it.
“Stuff it in me already!” she ordered aggressively.
“If that’s what you want…” I retorted, slamming my full lengthy into her in one fell swoop. If her vagina was wet earlier, she was absolutely drenched down and I felt very little resistance.
“Fuuuuuuck yes!” she groaned wantonly. “Tear my pussy up, Andy!” she demanded as she looked at me with fire in her eyes.
I grabbed onto her upright leg for leverage as I pounded my throbbing cock into her with all my might, arching my back as I brought my full attention to the symphony of pleasure centered on my penis. I closed my eyes as I used my other senses to take in all that was happening. I listened for clap of our bodies meeting while Jenny’s moans echoed in the background. I smelled the scent of our sex wafting in the room. I noticed the taste of Jenny’s pussy still on my tongue. And I felt the sensation of our bodies connecting in ecstasy.
I wished that I could live in that moment forever, but my body was responding to everything it was experiencing as I marched ever-closer to another orgasm.
Just as I was getting close, Jenny let loose a howl: “I’m coming AGAINNNNNNN!”
And as I felt her vagina clamp down on my dick, I was sent over the edge right along with her. I felt another river of cum erupt from my throbbing member up inside her pussy as she seemed to be on the verge of hyperventilating, her breathing was so fast and shallow.
“Holy. Shit. Holy. Shit. Holy. Shit,” she kept repeating in time with the spasms I could feel around my cock as it continued to unleash.
Finally, we both started to calm down and I pulled out of her before gently lowering her leg. How it wasn’t cramping that whole time, I would never know.
“Holy shit,” she said again, this time in apparent disbelief. “I’ve never hit four in one night. Never!” She grabbed my neck and pulled me in for a kiss. “Four!” she exclaimed again as soon as she released me.
With that she pushed me down on my back and climbed on top of me where she began kissing me again. The fervor with which she continued to make out with me along with the sensation of her dripping pussy on top of me re-ignited that feeling in my cock, as it began to grow again.
“You are not getting hard again?!” Jenny said incredulously. “I mean this in the best way possible, but you’re a freak, Andy.”
“I know. I know. It has a mind of its own.”
“As much as I would like to ride it until the dawn, I think my pussy has hit its limit. I’m sorry.”
“Oh, no need to apologize. There’s no expectation there and honestly I think I would start to lose skin if I attended to it every time it got hard. It’ll dissipate eventually.”
“Ok. Good to know. Speaking of winding down, we should probably actually get some sleep. Only a few hours until we have to be on the bus.”
“Yeah, you’re right. We should get at least a little rest.”
I turned off the lights and crawled back into the bed with Jenny as she nestled into my arms.
“Four! I still can’t believe it,” she whispered. “You’ve made me feel incredibly special tonight, Andy. Thank you.”
“I’ve had an amazing time, too, Jenny. Thank you,” I replied.
Before we knew it we had both drifted off to dream land.