Custom Harvest

When I was in college I spent 2 summers on a custom harvesting crew that started the season off in Texas and worked it’s way north up to the Dakotas and Montana. I was 21-22 for those summers and my boss was a great guy. He worked hard and was fun to be around mostly cause he liked to tease and had no problem getting teased if the opportunity arose. His wife and young kids would come along for part of the run but not the whole time. She was very nice also and they treated the crew great.

Midway through the harvest run we landed in your typical small Midwest town to set up camp. We lived out of super long campers which were clean but not overly spacious. We would probably be here for a few weeks as the boss, John, had several customers in the region. On one of the first days of harvest we got hit with a rain storm so that meant no thrashing for at least a day or 2. Most of the crew headed to the local pub to have some drinks and watch a ballgame on the TV.

When we arrived I immediately spotted a group of 4 young girls who appeared to be about my age. They were all quite attractive but the one blonde stuck out to me. She had a great smile and didn’t have that stuck up look. We all found a long table to sit down and when the waitress took our order I asked her to send another round to the girls table on me. John was buying for the crew so I figured I’d use the extra cash on the blonde girl. Once they got their drinks they waved a thank you over towards our table. I waited a bit and then one of the other young guys in the crew and I headed towards them to say hi and introduce ourselves. Her name was Jenny and she was gorgeous in my mind. She was obviously fit and had small/medium sized breasts. She was wearing jeans and a tight T-shirt. We all chatted as a group and then I asked Jenny if she wanted to go play pac-man on the old arcade game in the corner. I was desperate to get her alone and away from the group which now had 2 more crew members in the mix.

We played Pac-Man for quite awhile and I found out she was a nurse in the next town over at a small hospital. She was off till Monday and since it was Friday she was letting loose. She lived in town not far from the bar. Around 130, most of the guys had left and her girlfriends were leaving too. She said she wanted to stay with me and “ Get to know this Ryan fellow!” I was quite taken by her and her fun personality. Soon we were leaving the bar and I was being a gentleman and walking her home.

Outside her house we kissed and began groping each other and soon we were inside. It wasn’t long and Jenny was naked and giving me a blowjob. I’m not huge but 7.5” and have decent girth. She was very into it and gave great head. I warned her I would cum if she didn’t stop and that I wanted my turn going down on her. She said not yet, I wanna finish the job. Soon I was warning her again and she pulled off and jerked me onto her breasts. Once I caught my breath I dove straight in and ate her tight pussy. She was completely bald and tasted great. It took me awhile but soon she was convulsing and clamping her legs around my head. I was half hard again and looking for more but she said not tonight so we kissed and I walked back to the campground.

It was partly sunny all day and even though we tried it was too tough to harvest so we had the day to ourselves. We all went back to the bar for the steak supper they hold on Saturdays. Idiot me I didn’t get Jenny’s number but thankfully she and her one friend Sarah showed up around 830. I went over to her right away and was blunt as could be. “I want you number!” Jenny laughed and we exchanged numbers and started into a round of tequila at the bar. It was a slow evening and around 1230 Jenny invited me back to her place to watch TV. We were casually talking and flirting for quite awhile when I leaned into kiss her again. It wasn’t long and we were both naked and in her room. This time she was ready for sex and handed me a condom. She said she was on birth control but rather safe than pregnant! We went at it like animals and in my mind it was awesome. I ended up staying till the morning but had to leave at 8 cause we were gonna get the machines ready to try harvesting again.

The wheat was dry so we were able to start at noon and kept going without any problems until the rain clouds started creeping in again. Sure enough rained out at 830. I immediately texted Jenny to see if she was busy and she said to come over. I got there around 930 and we just snuggled on the couch when just before midnight an older woman around 50 walked in. It was her mom! I never knew she lived with her mom! Awkward!

Jenny introduced me to Tammy her mom. She was super nice and even said “So you’re the guy Jenny has been talking about!” Now I’m wondering if she was in the house the first 2 nights! After a short conversation, Tammy headed to bed and said goodnight to both of us!

Apparently her mom was a nurse too but was working evenings this weekend. And she was in the house but was cool with me being there. Her dad died when she was young so it was just the two of them. I got a text from my boss that said no work before noon at the earliest and of course he added, have fun! Jenny said I could stay the night if I wanted but she had to work in the morning at 7. Who am I to pass up sleeping over at a gorgeous girls place? We went to her bedroom and she stripped naked and so did I. We once again had sex with a condom but this time I was a lot quieter with my thrusts knowing her mom was just down the hall. Soon we were both asleep in her small bed. At 530 Jenny was up and getting ready, her job was about 45 minutes away. Even in her scrubs she looked hot. At 610 she was long gone and I was laying in her room snoozing for a few more minutes. Around 730 I heard her mom in the kitchen and soon I could smell breakfast cooking.

I only had my college sweats and a T-shirt to wear. Somehow I lost my underwear in the room and couldn’t locate them. I figured it would be fine to head into the kitchen to say good morning and leave her alone. Tammy greeted me with a smile and when I motioned that I was gonna leave she said to sit and eat first. Jenny said to take care of you and you don’t have to work till noon. At first I hadn’t noticed but Tammy was wearing a thin floral print robe that only went down to mid thigh. She was in pretty good shape for her age and you could tell her breasts were ample to say the least based on the outline of her robe. Watching her cook with her back to me I couldn’t help but ogle her legs sticking out the bottom of the robe and her fairly thick outline of her butt. It was likely part to Jenny making me so horny these past few days that I started to get a semi in my sweats. I must’ve been in a daze when Tammy spoke “Coffee?” cause I didn’t hear a thing. “Ugh, what?” I replied. “Would you like coffee?” Tammy asked again. “Yes please!” She motioned to the pot and I got up without thinking about my hard on and went to get a coffee. Tammy asked for me to pour her a cup too but with no cream or sugar, “I’m on a diet!” When she said diet I instinctively looked her up and down and said “ Why? You look great!” When I looked down she also gave me the once over and it was then she spotted my erection. I was turning red as was she but I figured whatever and pretended not to notice. I switched the conversation back to her and made note that guys likely hit on her all the time. She turned back to the oven and laughed “I wish, It’s been a while!” She then added “I wouldn’t know a ‘come on’ if it hit me in the face”.

Tammy was just like Jenny, easy to talk to and seemed very open. I figured I’d harmlessly flirt with her as I’m sure she wouldn’t mind considering her recent comments. I kept up some harmless comments like that she looked great and lots of guys I know would love to take you out and she continued to blush and be bashful about it. It was when I said “It’s a good thing I saw Jenny first or I’d be trying to live out my Milf fantasy’s!” Tammy looked at me puzzled, I could tell she didn’t know what a milf was. “What’s a milf fantasy?” I was shocked, surely somebody at the hospital had made a milf comment to her before. “You know, a Milf? Mom I’d like To F……? Young guy walks downstairs and sees a Milf cooking him breakfast in a robe. How small is this town anyways? You have Internet right?” I laughed out loud. Tammy laughed too, “yes we have Internet but it’s slow!” With that she motioned for me to have a seat and said breakfast was ready.

I went and sat at the table and she grabbed the pan of scrambled eggs and headed my way. This was when I said “Right now is when your robe is supposed to come open and I get a peek of your boobs when you bend over to serve the eggs!” She smirked, put the eggs on my plate, served herself and put the pan back on the stove and turned to grab the plate of sausages. “Does it have to be eggs?” Tammy questioned. “Nope, anything will do, toast, juice or sausages!” Tammy was still turned away from me as I sipped coffee. I could tell she was fiddling with something and when she turned around I knew what….her robe had quite the gap when she turned around and her breasts were very much on display. At first I wasn’t sure if I should comment on her robe or pretend I didn’t notice. She ended my thinking quickly when she asked if this is how the milf thing works? I swallowed hard and tried to act cool and said “ya, you’re getting it close to figured out!”

She put the sausages on the table and then sat down. The gap got much bigger when she sat down as the robe pushed out and up. I could almost see her nipples and could easily see the rest of her breasts. They were big and a bit saggy but I was more than excited as I now had a full blown erection. I tried not to be obvious but it was extremely difficult not to stare. I was trying to think of something to say that was witty or charming but my mind was blank. There had been quite a long pause in the conversation at this point. Tammy then broke the silence and asked me to pass the salt and pepper. I grabbed both with one hand and as I was reaching towards her I was beginning to lose my grip on the salt so I tried to set them down quickly but in doing so I spilled her coffee cup. The liquid starting to spill onto the table and was running toward the edge. Tammy quickly pushed back in her chair and she stood up to grab a paper towel from the counter while I stood up to move the dishes out of the way. In her hurry she completely forgot about her already loose robe. Although the belt was still tied the robe itself was completely apart in the middle from top to bottom. I still couldn’t see her nipples but I now had a good view of her vagina. It was obvious she had some hair down there but I could tell she kept it trimmed. Tammy was making quick work of my spill and soon she seemed satisfied with the job she had done. I said “sorry about this, I honestly didn’t mean to do that but now I’m glad I did.” Tammy had a puzzled looked on her face when I said that as she was oblivious to her state of undress. When I hinted with my eyes towards her robe she looked down and she quickly covered up. I told her not to be embarrassed, I liked what I saw and hinted towards my tent in my sweatpants.

Tammy stared at my groin for what seemed like a minute and then she said “Well it’s nice to know you didn’t find my body too revolting! Nice tent by the way!” I grinned and slyly said “Wanna see it, only fair after I got my peepshow?” Tammy sat back down on her chair and nodded. Instead of just pulling the waistband down over my cock I went for broke and stepped completely out of them. I stood there with just my T-shirt on and my hard on at full attention. Tammy just starred and then looked up at me and said “It’s very nice, thanks for showing me”. I then said “You can touch it”. Tammy looked back down, then up again then down. She reached out and grabbed me, gave a good squeeze and slowly gave my dick a soft up and down stroke. I stepped forward so she didn’t have to reach so far. Tammy continue to stroke me and soon she leaned ahead and began to suck my head. It felt wonderful and I think it was mostly because she was the mom of the girl I had sex with last night. She was sucking the penis that was in her daughters vagina less than 8 hours ago. She was now really going to town on my penis, sucking and licking the shaft like she was starving. Maybe it had been awhile for her. After a few minutes I figured the line had officially been crossed and I wanted to see what this new milf was willing to do. I grabbed her by the hand and pulled her into the living room and pushed her back on the couch. I untied her robe completely and kneeled down to start sucking on her pussy. It was amazing being between the legs of this mature woman. Even though I prefer bald vaginas hers was well kept and it was tasty as hell. All thoughts of Jenny were completely gone at this time. I was licking her clit and fingering her with 3 fingers. She was so wet, and it wasn’t long and she was starting to moan from my fingers and tongue. I figured this was my chance to penetrate her without her hesitation although I didn’t expect any. I quickly got up and pressed my cock into her and started to thrust at a steady pace. She wrapped her legs around me and now placed her own hand on her clit and began to rub in circles. Her tits were bouncing wildly and we were really getting into a rhythm. Tammy was starting to moan loudly and then she pulled me hard into her with her legs and let out a huge moan. She eventually released her grip on my torso and I asked if she wanted me to stop? “Keep going, I want you to cum too!”

I began thrusting into her although a bit slower than before as I was tired from last night. I hadn’t even thought about protection and she hadn’t said anything but I was getting close to ejaculating. “I’m gonna cum soon, should I pull out, are you on the pill?” With that she laughed again, “ I’m not gonna get pregnant, do what you like!” I assumed she either had her tubes tied or was on the pill, frankly I didn’t care anymore. I put my thumb back on her clit and rubbed hard, she protested that it was too sensitive, but I wanted her to come again. I rubbed hard and her moaning increased again but so was the sensation in my balls. I was gonna cum. I couldn’t hold back and I thrusted twice while shooting inside her and then quickly pulled out and came on her pussy and then aimed higher for her stomach and tits. Despite the action from Jenny last night, the whole ordeal from Tammy had me extremely excited and it showed. She was covered in cum from crotch to chest.

I rolled off and sat beside her on the couch. I put my hand on her thigh as we both were catching our breath. “Wow!” was all I could muster. Tammy just sat there and smiled and massaged her breasts lightly. She turned her head and said “Thank you for this! It has been a long time for me!” I still couldn’t believe what had just transpired. Tammy was lying there, caressing her breasts and massaging some of my cum into her skin. It was an erotic site to see and she didn’t seem to be in an hurry to get dressed or cover up. I watched intently but just from the corner of my eye. Despite having just cum, my penis was starting to take note of the mature beauty beside me and was starting to show life again.

She seemed to be in deep thought as she was still aimlessly caressing herself and starring out the window. I was now almost a full mast and since I had no idea if I’d have another chance with her I stood up and kneeled between her legs. I seemed to have confused her as she had a questioning look on her face but when I aimed my cock at her entrance she asked “Again?” I replied enthusiastically “oh god yes, I can’t have you just once!” With that I slipped inside her easily as she still had some of my cum leaking out of her. I began slowly at first but soon I was hammering away. Watching her glistening breasts sway to the motion of our thrusts was an image I will never forget. After a minute or so I asked her to stand and turn around. Tammy did and got on the couch with her knees On the edge and her face on the back cushion. Her plump ass looked great as I entered her from behind and I began a much slower thrust this time as I was getting tired.

Because I had just blown my load 10 minutes earlier I wasn’t anywhere near ready to ejaculate again so I was really trying to experience as much of her as I could. I once again asked to switch positions and I think she could tell I was tiring so she told me to sit and she would go. I sat on the edge of the couch in anticipation of her first move. She stepped over and straddled my legs but in reverse. She placed her hands on my knees and rode me. It was awesome watching her spread wide and bounce up and down on me. Her lips looked so amazing as they gripped my shaft. She rode me slowly as I placed my hands on her ass to help support her efforts. Tammy was my first older woman and it was an incredible experience so far. She seemed to enjoy it and savor the sexual experience like no one else. She eventually stood up and turned around, reached her hand out and gestured for me to grab it and she helped me up off the couch and led me down the hall. We ended up in her bedroom and she gently pushed me on the bed. I scooted up towards the headboard and her pillows and she crawled between my spread legs. She grabbed my dick and started to suck me . I couldn’t believe she would do this as I was covered in my cum from earlier and her own juices. She didn’t suck for long and soon was straddling me again but this time face forward. As she eased onto me both of us groaned, for me it was because of her. She was just amazing to look at, and amazing to feel. I felt like I was on cloud nine with this beautiful woman riding me. This beautiful mom of the daughter I was seeing.

Tammy rode me for quite a while, switching from her feet to being on her knees. When she switched back to her feet she put her left on on my shoulder and lifted her ass up and down, the full length of my shaft. It was when she took her right hand and began make circles on her clit that I started to feel my orgasm building. Tammy too was moaning harder and soon I couldn’t hold back any longer. I began to erupt inside her and she rode me and masturbated her clit. Tammy was determined to cum again as she continued to ride my cock and play with herself long after I had cum inside her. I was still maintaining a healthy Hardon but I knew it wouldn’t last long. Thankfully about a minute later she began to moan hard and slam down one last time as she started to cum while playing with herself. It was an amazing sight to see her enjoy herself. She eventually slouched ahead and fell onto my chest. I wrapped my arms around her and stroked her back and sides.

Tammy then spoke “I can’t believe I slept with someone so young, Twice! We can’t ever let Jenny know this happened. I don’t regret a thing but you have to keep quiet”. I assured her I would not tell anyone. Eventually she got off me and headed for the shower in her en-suite bathroom as she looked like she had just finished a workout at the gym. I was basking in the glow of our encounter. I was exhausted but very satisfied. I got dressed and through the door to the shower I said goodbye and left.

The week was busy with good weather helping us harvest. Jenny was busy working so I only stayed over one night and we couldn’t have sex as her period had come along. I was hoping for a blowjob but I guess that wasn’t happening as she soon fell asleep as she did work again first thing. Around 1130 I heard the first crack of thunder and soon rain drops outside her open window. Another day off for me, with that I crept out of bed in just my boxer briefs and headed for the kitchen for a glass of water. I thought I’d watch a little TV while Jenny slept in her room upstairs. Unbeknownst to me Tammy was working evenings again at the hospital and shortly before midnight she walked in the door to the kitchen in her scrubs. She walked into the living room and and in a low voice said “hey, how are you? Where’s Jen?” I replied “Sleeping!” Tammy said with a smirk, “Tired her out did you?” And with that sat down in the recliner. I said I wished but it wasn’t “happening” this week. We sat and talked about her day and how tomorrow I would likely have most of it off. She agreed as she said it had rained steadily on her drive home.

Tammy stood up and said she was headed for a shower as she had a gross evening at work. Watching her full ass sway as she walked away gave my cock some fuel after getting denied earlier. Before she was entering her room she turned and said “There is beer in the fridge, help yourself to anything you want” After a few minutes of thinking about our recent tryst I couldn’t contain myself and headed down the hall to her room, what I wanted was another round with Tammy. I could hear the shower running and seen her pile of clothes beside her bed. I wanted another peak at her as I was having trouble not thinking about screwing her again. With that thought I pushed the door open and walked in. Her shower had a curtain closing it and it was actually a full bathtub too. I peaked through the crack and could see she was washing her hair and was standing in the stream which must’ve been hitting her straight in the chest. I crept in behind her and grabbed the washcloth hanging on the handrail and began to wash her back. Tammy jumped but never turned and said “Do you think this is a good idea?” With that comment I nudged my hardon into the crack of her ass and said “Yep! You said help myself.” and continued washing her backside. Once she had all the shampoo out of her hair she turned to face me with lust in her eyes. I took her in my arms and began kissing her. We kissed for a minute or so and then I began kissing her neck and made my way down to her big tits and began sucking her nipples. I then pushed her down onto the little seat or ledge in the corner of the tub and began licking her vagina. After awhile, I stopped and looked around and seen what I was after. A lady razor. I grabbed it and held it up for Tammy to see what I had in mind. “You wanna shave me?” I began at her lips and was very careful to make her smooth. I wanted to leave a small landing strip as she had only trimmed before. Soon I was done and she looked incredibly sexy with her freshly shaved vagina. I dove in and began licking her clit and fingering her with 2 fingers until she came! After she caught her breath she told me to sit in her spot and now she was sucking me. Once I was fully hard I got up and bent her over and began to fuck her doggy style as she used the seat to hold onto. I was pretty worked up from shaving her and was gonna cum soon. I got her to turn around and told her to squat. I wanted to fuck her big tits and maybe cum all over them. After I got into a rhythm between her globes and using my hands to squeeze them together I replaced my hands with hers. I was gonna cum any second and warned her but she continued to push her tits together and I began to shoot ropes of cum up onto her neck and between her tits. It was an awesome sight, Tammy was covered again in cum but the water from the tub was rinsing it down her body and into the drain. She stood and looked at me but said nothing, instead I grabbed her again and began kissing her gently. She suddenly pulled back and said “Thanks again but you need to go!” I had to agree, so I slipped out, dried off and fled back to Jenny’s room and fell asleep.

Jenny was quietly getting ready for work and since I was so excited from last night I blatantly stroked myself in front of her to tease her. She just grinned and chuckled and said soon enough and kissed me goodbye and headed to the hospital. I texted my boss and since I knew he was an early riser I got an immediate response. No need to come in today. 2 inches of rain would put a stop to harvest for at least 2 days. Although I was ok with another day off I felt bad for John and the farmers. I got up and made a pot of coffee in hopes Tammy would wake and maybe I could fuck her again. Tammy finally awoke at 1030 and came out into the living room wearing her robe and I was on the couch watching sports center. She slumped down beside me and said good morning and made a comment about being exhausted from last night. I replied that I couldn’t help myself and how it was good that she slept in on her day off. We sat in silence for awhile as we watched the TV and then Tammy spoke “I know how wrong this is to sleep with someone half my age but I think that’s what makes it so good. I know I should say No but I just can’t. I hadn’t been with a man in years and it feels so good to be touched again!” I responded by rolling onto the ground in front of her, spreading her legs and began eating her pussy again. Eventually she came and I mounted her on the couch and fucked her till I reached my own orgasm. After that she and I went for another shower together and after I mowed her lawn. One of her neighbors stopped by just as I was finishing and Tammy was weeding her flower bed. She introduced me as Jenny’s friend to which I almost laughed at as I had been with her more times than Jenny now. After lunch we fucked again in her bedroom and then I left to go back to camp.

The next 3 weeks were filled with the most sex of my life. Often I had Jenny at night and her mom before I left in the morning. Once our work in the area was nearing completion Jenny and I agreed to at least keep in touch as we both knew long distance wouldn’t work. Tammy had a friend who lived near my college and told me she hoped to visit her and maybe we could meet up for a drink. I’m convinced this is the most erotic situation I’ll ever be in and although it was wrong to do that to Jenny, Tammy was just too good to say no to.

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