Double Trouble

I have been living alone for almost a year now since my son moved away to college and really enjoyed the freedom of having the house to myself. I had thought about the possibility of getting a roommate to help out with expenses and to have some company in the evenings when a friend from work introduced me to Jessica and said she was a school teacher that was looking for a place to rent for her and her daughter until she could find a house.

I told her I might be interested in renting a room and we could have a drink after work and talk about it. I ended up meeting her for a drink later that night and we hit it off really well. Jessica and her daughter Mary picked me up the next morning and we went out to breakfast and talked more about them moving in with me for a few months until they could find a house. It's a good thing the waitress seated us quickly because Jessica's tight little shorts and amazing cleavage combined with Mary's sexy one size to small Schoolgirl outfit was making my cock hard.

Jessica told me that she wanted to spend one nice relaxing day with Mary before they had to start packing and moving. She said they were going to the beach and asked if I would like to come with them. It sounded like a nice idea. I had been working really long hours lately and deserved a day off too. I told them I would love to come with them. Jessica said they needed to stop by their apartment to change clothes and get towels and swim suites on the way to the beach. After a few quick stops to pick up all the necessary beach gear we were soon on our way. As soon as we found a secluded spot and settled in they slipped off their short little sun dresses and proudly displayed their tiny stunning bikini clad figures. Jessica is 38 years old, 5'5" tall, 110lbs with long black hair stunning green eyes a beautiful pear shaped ass and a set of 36 c breasts with nice little pencil erasure nipples and a slim waist.

Mary is the cutest teeniest little fuck muffin I have ever laid eyes on and she rocks the whole emo girl look. Mary has bright red hair with deep blue eyes is 4'10" tall weighs about 90 lbs. 19 years old with tiny little tennis ball tits and hard little nipples that always show through her shirts. She has a tiny waist and a cute little bubble butt that just begs to be touched.

The weather was great and we had a lot of fun swimming in the ocean and lying out in the sun catching a tan. The girls were very playful and asked me several times to rub lotion on them and at one point when we had the whole beach to ourselves Mary asked her mom if she could go topless for a while to even out her tan. Jessica looked around to check the beach and said

"Ok Mary as long as Dan doesn't mind and if anyone else comes you have to put your top back on."

Mary had a huge grin as she thanked her mom and then asked me with a giggle if it would be ok if she set the twins free. I smiled back at Mary and told her it wouldn't bother me one bit. I lied. I was already having a difficult time keeping my thoughts at bay with Mary and Jessica strutting their tight toned tan tasty little bodies in front of me. When Mary looked me in the eye and slowly bit her bottom lip as she made a sexy show of removing her tiny bikini top l knew it was going to be hard to keep from getting an erection.

In the sweetest voice Mary asked me if I would please rub some lotion on her so she wouldn't burn her cute little boobies. As I was putting the lotion on my hands and getting ready to rub it in Jessica says "make sure you get her nipples really good, the last time she tanned the twins she missed a spot and cried for two days about how sensitive her nipples were."

I rubbed the lotion all over Mary's little boobies and as I used my thumb and finger to massage the lotion into her nipples she let out a soft moan. By the time I was finished Mary was breathing hard and my cock was as hard as her nipples. The tip of my erection was just barely peeking out of the leg on my shorts and I noticed Mary taking a quick look.

She gave me the sexiest little grin as she looked me in the eye and said thank you curling her silky soft finger around the sensitive tip of my erect penis as I was turning to lay face down on my towel to hide my raging erection before Jessica noticed it. I had just managed to go from rock hard to firm before I heard Mary say

"Hey Mom, Dan's looking a bit pink, I think we should put some lotion on him."

Jessica said ok and put down her book sitting up to scoot closer to help Mary rub lotion on my back. It felt wonderful to have two sets of hands rubbing lotion on my back and when they got to my legs they each straddled a leg and worked me from my toes all the way up the legs of my shorts to my balls before they both said with a giggle

"Ok turn over"

I carefully turned over trying to hide my erection from the girls but the outline of my stiffening cock was clearly visible as it tented the leg of my shorts. The girls gently applied the lotion to my face and neck before working their way down my chest to my legs. They each straddled a leg and massaged the lotion firmly from my toes all the way up under the leg of my shorts to the top of my thighs.

As they rubbed the lotion on my legs I could feel them sliding their bikini clad pussy lips on the tops of my feet as they moved back and forth. By the time they finished my cock was rock hard and oozing precum. Jessica wrapped her soft hand around the shaft and said.

"Mary look what you did to Dan, you've been a very bad girl, I might have to let Dan spank you when we get home."

Mary giggled and said.

"It sure looks like something needs to be spanked."

The sun was starting to go down and we were the last ones on the beach when we decided to call it a day and hit the showers on the way to the car. The showers had a high wall around them giving them some privacy and the beach was deserted so we had the place all to ourselves as we rinsed the sand and lotion from our bodies. As Jessica was washing my back Mary started pulling down my swim suit saying

"Dan, give me your suit so I can rinse it out"

As I stepped out of my suit Jessica soaped up my erection and washed it thoroughly. When Jessica finished washing me she handed me the soap and said with a giggle.

"My turn"

As she removed her bikini top and handed it to Mary to rinse I began soaping up Jessica's amazing body. I followed her example and washed every inch of her fine body. Mary pulled off Jessica's bikini bottoms and I made sure to rub that slippery soap all over Jessica's pussy and ass until she was breathing hard and softly moaning. As Jessica finished rinsing the soap from her body she looked at Mary and said

"It's your turn young lady, Dan? Will you soap her up while I rinse out her bikini?"

I took the soap from Jessica and admired Mary's bright red landing strip as I started soaping her up trying to pretend that running my slippery hands all over every inch of a gorgeous tight petite 19 year old wasn't arousing. When I told Mary I was finished she looked up at me with a disgusted look and without breaking her stare she said.

"Mom, Dan's a little shy, would you please tell him it's ok to use his fingers and thoroughly soap up every inch of my sweet little pussy and ass so I don't go home smelling like a clam?"

As Jessica finished rinsing Mary's bikini she said.

"Dan? Don't be shy, it's no big deal, please scrub her little kitty good, I don't want my car to smell like fish tacos."

As I started rubbing the soap on Mary's tiny pussy and ass I heard Jessica giggle and say

" Just don't wash her too deep she's still a virgin."

Mary blushed and said.

"Oh Mom stop it, you embarrassed me in front of Dan."

I did as asked and scrubbed her good soaping up my fingers and sliding one into the tight opening of Mary's vagina to make sure she was squeaky clean inside and out. As Mary stared into my eyes with a blank expression I finished washing her and as I started rinsing her I cupped my hand and bent my middle finger slipping it just inside her tight virgin pussy. As the water from the shower filled my cupped hand I finger fucked her tiny pink opening rinsing her out until she started squirming on my finger and moaning. I pulled my finger out of Mary's tight little kitty and smiled at her as I smelled my finger before licking the tip and looking her right in the eyes I said "it smells as good as it tastes."

Mary smiled right back and slipped her finger in her pussy before running it under her nose and sucking the tip as she gave me a sexy grin and said.

"You have good taste Dan and you're right, I do taste good."

We all dried off and the girls slipped their little thin sun dresses back on and wrapped up all the wet swim suits up in their beach towels. I didn't have an extra pair of shorts so the girls suggested I just wrap the towel around me for the ride home in the car.

I wrapped the towel around my waist and we loaded our stuff in Jessica's car and started our journey home. As we headed down Pacific Coast Hwy Jessica asked if she could stop for just a minute and pick up a painting that she was having framed. She stopped at a little art boutique and soon came out with a large painting. It was too big to fit in the trunk so after thinking for a minute Jessica said.

"Dan the painting has to go in the back seat is it ok if Mary sits on your lap for the rest of the way home?"

Before I could answer Mary says.

"Please Dan, I don't weigh very much and my little butt is really soft so it won't be uncomfortable for you?"

I told the girls that I didn't mind and to just drive safe and careful. Jessica carefully put the painting in the back seat as Mary climbed in the front seat and planted her sweet little ass on my lap. As Mary sat down she lifted her short sun dress to keep from sitting on it giving me a beautiful view of her lightly tanned ass cheeks. As we drove Mary leaned back into my chest and grabbing my hands she pulled them up and placed them on her chest covering her perky little breasts as she said.

"I don't have a seat belt will you hold me so I feel safe?"

I cupped Mary's perfect little boobs and felt her nipples harden in my palms as my cock stiffened under the towel. Just before we turned onto Las Virgenes Rd Jessica pulled into Starbucks to grab a coffee for the ride home. Jessica ordered coffee, Mary ordered a cinnamon roll and I had juice. As we turned onto the canyon road leading home it was just getting dark. Mary leaned back into me placing her lips to my ear she said.

"Do you mind if I get comfortable?"

Before I could answer Mary reached under her dress between her legs and moved my towel to the side removing the only barrier between my throbbing erection and Mary's freshly washed little virgin pussy. Mary purred in my ear.

"Oh that feels so much better."

Mary's tiny pink silky lips were straddling the top of my shaft kissing the ridge and foreskin just below the swollen head as Jessica drove on in the dark oblivious to the dangerous little game that Mary was playing. As we drove Mary would wiggle her little butt in my lap and move her pussy slightly back and forth on the top of my shaft stimulating my heavy erection. Every time we went over a bump in the road the weight of my bloated shaft would drop down and then lift up and slap against Mary's tiny pink opening stimulating her clit with each slap. On one stretch of road it was so bumpy that my cock head was slapping her clit so quickly that she moaned and burst into laughter causing Jessica to look over and ask what was so funny.

Mary thought quickly and told her it was the lyrics in the song that she thought was funny but I knew better. I felt her nipples harden against my palms and her little pink lips making the top of my cock slippery with her juices as she began to get excited from our intimate contact. I was getting those feelings that tell me I'm getting close to having to slow down the stimulation or prepare to let the load fly. I whispered in Mary's ear. "Please hold still for a minute"

Mary reached under her dress and swiped her finger up the bottom of my shaft and right into the goo leaking from the tip of my over excited cock. Mary pulled out her hand with my precum covering her finger as she said.

"Oops, I almost made a mess on your car seat Mom. The frosting from my cinnamon roll was about to drip but I caught it with my finger."

Mary licked my goo off her finger and said

"Oh Mom, it's so yummy you should taste this."

Jessica said "well sweetie, if it's that good give me a little taste."

Mary slid her hand along the bottom of my shaft again scooping up the slippery goo on her finger before she reached over and slipped her finger between Jessica's lips. Jessica sucked the goo from Mary's finger and said.

"Yum that is good I wish I would have ordered one."

I sat there mortified worrying that Jessica would find out what Mary was doing and throw a fit and in the process my erection started to soften. Mary reached under her dress and tickled the bottom of my shaft making it jump and smack her wet pink lips. Mary slid my slippery cock head against her tight wet pussy lubricating it before she stuck the tip in her tight opening.

As soon as I realized what happened Jessica hit a bumpy section of road and Mary's tight slippery pussy was bouncing on the tip of my cock bringing me back to full erection in a matter of seconds. It felt so good having her wet tight opening caressing the slippery tip of my cock as we rubbed against each other with each bump in the road.

I was going through sensory overload. I was feeling a little vulnerably wearing only a beach towel wrapped around my waist and the indescribable pleasure being thrust upon my throbbing erection was pushing me right to the brink of orgasm. The overwhelming feeling of having no control over the situation as Mary pushed me closer to orgasm with her Mother sitting only three feet away was both exciting and scary.

It was exquisite torture sitting there with this cute petite sexy way too young virgin massaging the slippery tip of my erection hidden under her short dress while her Mother drove on humming to the music on the radio. I don't think Mary knew the full danger of her little tease, but I knew something she didn't. She was so tight that the thick head of my penis was too wide to just slip in but she kept pushing back and teasing like she was going to push harder and take the head.

Each time she moved her wet little pink lips against the precum slippery tip of my erection she increased her chances of getting an unexpected hot cream filling. I was worried because I knew that I was already having a hard time keeping myself from losing it and spraying spunk all over Jessica's car and now that Mary had her little pink opening capping the blow hole on the tip of my erection the penalty for losing control was much more serious.

I also knew that if I came with the tip just touching Mary's opening that the pressure and volume would exceed the limits of the connection and spillage would occur which Jessica would surly smell and recognize as fresh sperm leading to a situation that I wanted to be no part of. I was really proud of my control as we got to the end of the canyon and turned onto the freeway on ramp right up to the point when we hit stop and go traffic.

Now instead of Mary's little opening bumping and rubbing against the tip of my erection over the bumpy road each time Jessica would start moving it would push Mary back in the seat and press the tip of my penis against Mary's tight opening just short of spreading her wide enough to allow the thick head to slip completely inside and then when the car would stop it would push her forward lessoning her contact until the tip just barely touched Mary's tiny pink lips.

The one thing Mary was completely unaware of was that I have a fairly unique shaped penis that has a very wedge shaped head with an extremely thick ridge or crown as the head and shaft meet. I knew from experience that if she accidentally pushed too hard and actually made it past the thick ridge she would be very surprised and have a hard time keeping quite as she was stretched wide for the first time.

I was already concentrating hard to keep from blowing my load and knew if Mary slipped past the head the pain would make her squirm and try to pull back off the head to relive the pressure and the tightness of her opening combined with the thick ridge on the head of my penis would take her considerable effort to pull past the ridge and get the head back out of her tight opening.

I knew that if she went too far and managed to get past the crown I would lose my load as soon as I felt Mary's hot silky lips slide past my cock head and kiss the shaft. I was aware of the fact that Mary's little vagina was so tight and with the thick ridge surrounding the head of my penis it would keep every drop of thick potent sperm inside her until I pulled out and after being teased all day by Mary and her Mom it would be a huge load.

I was praying that I could hold out for another two miles of stop and go traffic before we got to our off ramp and very thankful that Jessica didn't drive a stick shift. I could feel the perspiration forming on my forehead as I tried not to surrender to the amazing feelings Mary was forcing on me. Just as we were getting off the freeway Jessica looked over and said.

"You look a little flush Dan, are you ok?"

I smiled and told her I was just hungry after a long day at the beach. Jessica asked if it would be ok if her and Mary dropped me off at home and then went to the grocery store to pick up a movie and some stuff to BBQ for dinner then home quickly for a change of clothes and then they would come back and make me a nice dinner and we could watch a movie together after.

I gave Mary's perky little breasts a squeeze as I told Jessica I would love a nice home cooked meal and would enjoy their company very much. Jessica pulled up to my house and I did the best I could to hide my erection as I covered up with the towel while getting out of the car. I told Jessica and Mary I would start getting things ready while they went to the store and would see them when they returned.

I quickly set the table and lit the barbeque before straightening up the house a little and putting on some music. I had everything ready and decided to take a nice relaxing shower to wash my hair and jerk off so I could relax for the evening and not fight an out of control erection. I put a note on the door for Jessica and Mary telling them I was taking a shower and to come in and make themselves at home.

I just finished remodeling my master bathroom and installed a nice big shower with enough room for easily four people. I fired up the shower and made it steamy hot as I washed my hair and enjoyed the feel of the hot water massaging my back. I took a big glob of liquid soap and lathered up my cock as I closed my eyes dreaming about Jessica's beautiful lips wrapped around my cock as she looked up at me with her sexy bedroom eyes.

I was stroking away and just short of ejaculation when I heard the shower door open and two giggles followed by two sets of feet splashing on the shower floor. I opened my eyes to see Mary and Jessica standing in the shower completely naked with wide eyes staring at my large throbbing erection as they both said.

"I think it's clean"

We all started laughing. Jessica said.

"The sign on the door said you were taking a shower and to come on in, so here we are."

We all had some relaxing and stimulating fun in the shower and this time I wasn't shy about washing every inch of Jessica and Mary's amazing bodies and they both took their time exploring every inch of my body too. We dried off and I pulled on a pair of silk boxer shorts as Jessica eyed me with a sly smile before she said.