Chapter 20: Mary - Part 1

Mary was a total surprise the first time I met her. As the mother of my current girlfriend, I would have had to meet her, sooner or later - it just happened to be way sooner and not in anyway I’d expected. The first night I picked her up, her mother met me at the door, mentioning Caroline creamed her jeans just talking about me. This was something a teen’s mother NEVER spoke about and if she knew I was affecting her daughter in this fashion, MOST would have shown me the door, and THIS was the first time I’d met her.

I’d promised to take her out this coming Friday night and the time was upon us. Asking her what she’d like to do, it was a trip to the A&W drive in because she wanted to bee seen with me, according to her. We sat until it became late evening. I suggested we go to the drive-in movie. I thought she’d lose her mind! I don’t think I’d ever ran across a girl so anxious to go to a drive-in. Sounded promising but I’d soon develop a case of blue balls from it. Kiss, yes, touchy-feely ... not happening. Caroline was SURE this was the end of our new romance and started crying. I apologized and she told me she ‘wasn’t ready for anything like that’. I made some lame excuse about being a guy and just did a guy thing with a pretty girl.

By the time we got to her house, she was in a lot better mood and wanted us to go out the next Friday, but try to come over early.

Friday night hit and went to pick up Caroline for our promised date. Her mom answered the door and she totally shocked me with her next words:

“Caroline is in her room dressing, why don’t you just go on in. I’m sure you’d both enjoy it”, or something to that effect. How many teen males get THAT kind of invitation, especially from a girl’s MOTHER?

With some reluctance, I knocked on Caroline’s door and was invited in. Caroline stood in a white pushup bra, panties and a garter belt. She yet to don the thigh-high hose laid out on her bed. Talk about an instant boner! I’d have a few other girlfriends meet me totally nude, but this was a naïve young woman I had just met. She finished dressing as I worked to re-arrange my johnson so it at least wasn’t trying to poke over the top of my jeans. Caroline decided it was time for a serious talk- about me going to A&W after our date and getting a little ‘strange leg’ there. I told her why and told her I respected her stand on staying chaste but didn’t feel the need to be that confined. She could live with it, give in to it or I’d back out of the whole relationship. Understand - I wasn’t trying to be an asshole, we weren’t really committed yet. I really LIKED Caroline, she was sweet and pretty and had a killer bod, but I was used to a little more non-committed sex than this. I wasn’t going to fall in love with anyone else and wasn’t going to force her to do anything she wasn’t comfortable doing on her own. Caroline told me she wanted some kind of commitment. I could live with that, as long as there was light at the end of the tunnel.

Caroline became a fixture in my life- going to gigs with me and spending all our free time together. It took a few months, but Caroline finally gave up her chastity belt. We did finally fuck and I learned she wasn’t a virgin. Seems one of her mom’s earlier boyfriends had raped her, several times, until her mom found out. Short story long- I was invited over for coffee then next morning to talk with Caroline AND her mom.

Mary, Caroline’s mother wanted to talk about the sex we’d had the night before. I was looking for a place to hide. Moms just did NOT talk about this with her daughter OR her boyfriend, especially if said boyfriend was sting right there. My girl went on to explain she’s spilled all to her mom after coming home and Mary was thrilled on several levels - ONE, I hadn’t freaked out when I found out why she wasn’t as virginal as she’d acted, TWO, that I’d shown her little girl love making instead of a fuck, and THREE, SHE was turned on by the whole situation to say “My panties are wet just talking about the sex you kids had.”. TMI. WAAAY too much information.

Mary’s next revelation floored me - Caroline mentioned she wanted to do it with lights on and Mary wanted to watch. She went on to say she’d lost her cherry to her dad at age ten and it had been a loving relationship for several years. She wanted Caroline to enjoy sex as much as she had. I STILL had a feeling she was living vicariously through her daughter.

In Caroline’s bedroom, my girl lost ALL her reluctance, shedding clothes like they were on fire. Mary commented on the size of my dick. That was nearly enough to shrink what started as a nice hardon. She also encouraged her daughter to handle it, then give me a blowjob, convincing her to swallow her first time. I learned Mary was into ass play, telling C to feel for my prostate and rub it. I hooked Caroline’s legs over my shoulders and eased in to my balls. It took about five minutes of long-dicking her and she let out several moans and then a scream. Mary looked on with more than a little envy as her ‘virginal’ daughter fell into a deep sleep after giving her two intense orgasms. I wondered what was coming next. Mary was flushed and panting like a bellows, obviously excited herself.

Pulling me around by the shoulders, Mary kissed me deeply. She informed me that she wanted to share me with her daughter, if being with an older woman didn’t turn me off. Later, I found out Caroline and he mother HAD discussed me and the possibility of some kind of sharing thing. Caroline was apprehensive but got over it. What bothered her was the big gap in sexual experience. A few hours later, we were back at her house and mom made it known we were going to party hearty.

Mary met us at the door in a housecoat she hadn’t bothered to tie. This was the first I’d seen of Caroline’s mother, in the flesh, so to speak and she made no move to cover herself. Mary told Caroline since she’d gotten all the goodies this morning, it was her turn this afternoon.

She led her daughter and I into her big bedroom. Her king-sized bed left room for everyone to get comfortable and as soon as she got near the bed, the housecoat came off. Mary didn’t have a teenage body, but what she did have was tight, upturned breasts, a slender waist and a shaved pussy. She lay back and pulled me on top of her, bringing my head to her lips. After swabbing my tonsils, she pushed me down to her chest. Sucking on her nipples got her to purring contentedly and she surprised me by pushing me on down to her crotch and pulling her pussy open.

“Eat me, stud!” I didn’t need any more invitation than that. Mary’s sopping pussy was sweet. I could taste some fruity flavor there along with the tangy aroma of excited woman juice. I licked her from asshole to clitty and Mary about collapsed my skull trapped between her thighs. For a small woman, the gal had muscles.

I concentrated on her hard clit sticking out the top of her slit. I was amazed at the size of it - as big around as the tip of my pinky and it extended three quarters of an inch beyond its hood. Here was actually something to wrap my lips around and chew on.

“Oh GOD! Chew on my clit ... suck it hard, ... bite it!”

Ok, I can do that. Let’s see what she’s up for. To this point, she hadn’t given me any indication that she wanted slow loving. I pushed two fingers into her pussy. Her response was to jam herself down on them, obviously she liked that ... a lot. She was hunching on my fingers like she wanted them in up to her navel, so I added another to the mix, twisting my hand around in her tight twat. I didn’t have to mash her G spot, she did that all on her own. Her juices were so copious they were pouring down her ass crack onto the sheet. I’d been rolling a nipple between two fingers, keeping it stiff and hard but decided she might want a little more personal invasion, so I took that hand and scooped up some of her generous juices and rubbed her asshole.

“Finger my ass, cram it full!” she gasped, “Buck, I won’t break. I want it rough. I’ll tell you if it gets too intense ... I’m making up for the last 15 years of having to get myself off.” Hard to believe she’s been solo all this time - she was a good looking woman.

Between mauling her G spot with three fingers and wallowing her out her ass with two more, Mary sailed off into the ozone. She back arched like a bowstring until she collapsed on the bed. Caroline had gotten down to the foot so she could see all I’d been doing with my fingers and tongue. I took the hand out her mother’s pussy and wiped Caroline’s lips with my soaked fingers. She got her first taste of pussy. Evidently she liked it because it took almost no urging until she buried her face in her mom’s crotch. Mary, recognizing her DAUGHTER was eating her pussy, came again.

We took a breather to go to the bathroom and get a drink. Mary was feeling pretty mellow but Caroline was raring to go. As she lay back on the bed, I started to get over her when Mary latched onto her hard little nipples. I watched Caroline react as her mother brought her a very pleasant buzz. What shocked me was Mary kissing down C’s body until she captured her stiff clit between her lips. Soon, Mary was muff diving like it was her last meal. Caroline went berserk. Wiping her mouth, Mary leaned back and told us this was the first pussy she’d ever tasted. When Caroline was in charge of her faculties again, I rolled her over for her first doggy-style fuck. She climaxed in a heartbeat and passed out. I was still maintaining my hard on.

Mary wanted to just let her sleep it off and pulled me into her big bed, explaining SHE wanted fucked.

“Fuck me doggy style like you did her and then fuck my tight little asshole.”

She was already wet, both from playing with her before and sucking C’s pussy. She positioned herself, ass up and head down on her arms. This would be our first fuck together ... everything else seemed to lead up to this point.

The lady was tight. 15 years of doing without must have shrunk her to near virgin status. I slid into a velvet glove and I could feel her vaginal muscles rippling and squeezing my dick. Oh Yeah! This was going to be outstanding. I asked her if she played with any toys and she mumbled something about having a tiny vibrator, then expanded my ego telling me I was the biggest thing she’d ever had in her pussy. I told her she had a remarkable twat, as tight as her daughter’s. Mary was meeting my thrusts with her own, slamming her ass back as I pushed forward. I sped up my thrusting and I could feel her pussy clench my dick, both going in and out. Her breathing got ragged and a low moaning came from her mouth and I felt her shudder.

“Cum in me, Buck.”

“I will, darlin, I’m saving it for a bit.”

She had a bottle of lotion in bed and after pulling my rock hard dick from her tight pussy, I opened it and coated her tight asshole. I was kind of surprised she hadn’t tightened up from the ass play we’d done earlier, but there’s a lot to be said for experience and she was able to totally relax. As I took the time to work some of this lotion into her butt, she told me:

“Buck, like I said earlier. Sometimes I like slow and loving, other times I like it rough. You’re not going to hurt me. I’ve been without a long time and I want you to make me feel it. I need to feel like a woman again, so fuck my ass and fuck it hard!”

I teased her ass, rubbing it along her crack and over her tight little pucker. I think it heightened her anticipation until she thought I was going to continue to just play with her. Once she stopped squirming, I filled her ass with about half my dick.

“SHIT!! You’re splitting me in half!”

“Want me to stop?”

She let out a quiet “No.” I did give her a minute to accustom herself to the intruder. I made slow movements in and out, not more than an inch or two either way and she got into her own motion, slamming her ass down on my dick. I could feel my balls slapping into her pussy every time we collided. She gave a slow gasp and moaned out she wanted more. The only thing I could do was spread her ass cheeks to gain another inch. I loved watching Mary’s sweet ass swallow my dick.

“OH GOD!” she screamed, “OH FUCK! AHHHH GOD! ... OHhhhh FUCK MEeeeee!” Mary yelled and pounded the bed with her fists. I put my hands on her shoulders to pull her back on my thrusts three or four times until I started spraying cum in her. After the first hard squirt, she moaned and screamed loudly. I felt her rosebud tighten up around my throbbing cock as I kept blowing my baby batter just as far up in her bowels as I could.

We lay beside each other, her with her head on my chest and me rolling a nipple on hers.

“Mary, we need to talk about some things.” Mary rolled over on top of me with her legs astride mine, cuddling.

“What, lover?”

“I assume you’re still fertile and I KNOW Caroline is. Wouldn’t you think it’s prudent for you both to get on the pill?”

“Wow, I hadn’t even thought that far. You have to admit, this is all going rather quick, but that’s an excellent idea. I wouldn’t mind having another baby, although a 35 year age gap would be a little awkward. C SURE doesn’t need that hassle. You haven’t come in her yet, have you?”

“No, our first time, I used a condom. I haven’t cum, not in either of you. Your ass doesn’t really count.”

“This is serious business, but it just gets me excited. As odd as it sounds, I’m hoping we can do this on a regular basis. I LIKE having you here with me and I know C loves you.”

Caroline must have came awake after hearing her mother let out the war hoop a few minutes prior. She came in her mom’s bedroom and stared at her mom’s ass as my spunk dripped out of her.

“You fucked mom’s ass!” Talk about belaboring the obvious.

“Mary, you and C need to have some another mother/daughter chat. We’ve thought up a valid hygiene question that concerns you both.”

Caroline wanted to know WHEN I planned to introduce her to anal sex. I let her and her mother have their little talk while I got some fresh coffee.

The ladies were gone long enough for me to start sipping my second cup. Mary was full of questions herself. I think it finally dawned on her what we were getting into. She asked me if I thought she was a ‘pain slut’. I reassured her I didn’t. Like she herself felt, at times, we all like it a bit rough.

Caroline came out and again stated she wanted to try anal sex too. I wondered if this was following her feelings that her mom was leaving her in the sexual dust. If her mom did it, she wanted equal time.

The three of us went to C’s bed. I got her prepped by rimming her then oiling her tight little ring. Once I got her to relax, I got in position and eased in her backside. Suddenly, my dick was in a flesh vice and she immediately tighten up, nearly pinching my dick off. Caroline was clenched tight enough that any further penetration wasn’t going to happen without it hurting her and me losing some valuable skin. Mom got in the act and crawled under her to suck on her clit and finger her pussy. She soon relaxed again. Between the quivering caused by her mom on the bottom, C got into motion, bucking back to meet my thrusts into her tight little ring, and she came hard. I was pooped myself and stopped holding back, filling her ass with what little cum I had left. I went to the bathroom to clean up and we decided it was time for some shut-eye.

I woke up to a full bladder, a blowjob, a latex covered fuck and another anal session with Mary. A piss-hardon is a wonderful thing until your bladder gets TOO full. The girls had their heads together talking when I got back from draining the main vein. Getting everyone together, I suggested we clean up a bit, then go get some breakfast somewhere - my treat. We had waffles and a country breakfast. As we ate, both ladies were looking at each other, like each was waiting for the other to speak.

“Buck, I know you love Caroline, but I’m developing feelings for you too. We want this to be a group thing for as long as it lasts.” Wow! Two hot women and they both wanted me. My mind shifted back to the other three that shared me for nearly a year. Mary was in their age bracket, so that didn’t bother me at all. Caroline, more like the two younger ones I’d shared. I hoped this new relationship had a longer lifespan.

Uncle Sam caught up with me and the rest of my band members. As I reluctantly pushed off to join the ranks in green, Mary and Caroline promised to stay faithful and write me regularly. [I won’t bore you with a repeat of my Army adventures - read Caroline if it interests you.]

I was free, or nearly so. After doing my tour, I found that Uncle Sam needed my attention in the ready reserves for a few years.

Mary – the journey begins...

It didn’t take much persuading to get me to move in with my two ladies shortly after I got home. Both ladies tried to make up for lost time, often to the point I was exhausted. Not being content to be a house guest, I had to work, so I joined a bridge crew on the ‘Frisco’ railroad. The pay was great, the hours long and hard. The worst part was being away from my women sometimes for a week at a time. Caroline changed. I had changed. I guess the real truth was I’d grown up, seeing the shit I’d experienced in ‘Nam. C got ‘clingy’ and started in with this ridiculous baby talk whenever we were together. I think the whole town assumed we’d get married but the childish way she had around me was like fingernails on a blackboard. We’d had several major fights over it and she decided to move out to her own apartment. Mary very persuasively clarified that nothing had changed between the two of us, meaning Mary and myself. C got on with her life and Mary and I explored as many aspects of our imagination as possible.

Mary, after cornering me several times, got me to tell the story of my time and experiences in my summer ‘cabin’ years ago. I was reluctant to get into specifics, but Mary insisted. As the story played out, it was an after-sex chat. Mary wanted every ‘sordid’ detail. What was it like to educate two teens and my young bud into the world of sex? She was appalled then juicy to the point of having me ream her ass soundly after hearing of my friend’s sister getting her anal cherry auctioned off by her parents. The whole swinging thing got her cookies off more than once. Believe me, I REALLY tried to explain that although I’d known some of this ‘deviant’ behavior, it was a learning experience for me too.

What turned out to interest her more were my escapades with the other Mary, maybe because of the age difference and the fact THAT Mary was making up for lost time and nothing was taboo, AND my time with the three women in a lone cabin for nearly a year. I think maybe Mary missed the group sex between her daughter and ourselves.

Mary had a lady friend at work, a year or two older than herself. Evidently, the two had more than casually discussed our whole relationship. Bottom line was that Darla wanted in on the action. This story is about Mary, however, I’d be remiss to leave out Darla.

Darla...

I’m not going into a lot of details about Darla, other than to mention she was a fifth year divorcee from a clueless husband. According to her, not only was he without skills or imagination in the bedroom but possessed a minuscule penis. I’d never met the guy. Mary got the three of us together for a dinner out. Darla explained that with her disillusionment with marital sex, she abstained from sex since. After a pleasant meal with only a few pointed remarks about OUR sex life and HER lack of one, Mary invited her to the house for a drink and more conversation.