Pathways to Love

After a few minutes, she decided she wanted to be on top. She gripped me and rolled me over, no easy feat in a Twin XL. She leaned back and enjoyed my cock completely filling her up, me enjoying the sight of her flawless body on top of me. She than leaned over and started riding me slowly, ensuring that her breasts were directly in front of my mouth.

Figuring that this was no accident, I started kissing and licking her breasts, eliciting moans from Beth. She started riding me harder and harder, her moans getting loud enough, that I started wondering what my neighbors were hearing. It wasn't long before she informed me/my neighbors that she was having an orgasm.

"I'm cumming! Ted, I'm gonna squirt!!"

And sure enough, she shot my cock out of her cunt and sprayed onto my sheets her girl cum. She was shaking and shivering for a few seconds, but then grabbed my cock and guided it back inside of her.

She kept up the rhythm she'd had before, leaning up a bit so I could see her tits bouncing. I placed my hands on her ass and started massaging her cheeks as she continued her ride. She clearly liked it as she moaned every time I did it hard. After a minute, she leaned over, and her face was directly in front of mine.

"Put your finger in my ass," she whispered. I was stunned. Never before has a woman even remotely been ok with me being anywhere near their assholes. I'd even licked a girl's once by accident and she was grossed out. She took my right hand from her ass cheek and stuck it in her mouth, still riding me up and down as she lubricated it with her saliva.

Once she thought it was wet enough, she took it out of her mouth and put my hand near her ass crack, leaning over a bit to give me better access. I could feel her puckered entrance with my fingertip and started teasing the outside of it, Beth's face showing me she liked it. After about 30 seconds, I inserted the tip of my finger inside.

If I thought her pussy was tight, her ass was even more so, it almost seeming to try and pull my finger as deep into her bowels as possible. Her reaction to the new intrusion was immediate.

"Oh, fuck!" she said in ecstasy. "Finger me! Finger fuck my ass while I ride your cock!"

I kept my pace up while she was on top of me, but also was plunging my finger in and out of her ass at the same time. The sensation was too much for her as she came again.

"SHIT!!!" as she exploded again, but not enough to kick my cock out of her snatch. It was enough to send me over the edge and I blew my load in the condom. The look on her face showed she knew I'd came, and she smiled as she leaned down and kissed me deeply.

"That was amazing," she said as she snuggled up to me in the bed. "But just so you know, I totally would've let you cum on me."

I was in love from that moment on.

No matter what was to come...

Two Years Later

Unlike most people on spring break who were going to Florida, California, or the Carolinas, I was heading to my girlfriend's parent's house.

From the day of our first date, Beth and I had become inseparable, falling for each other instantly. The whole rest of my sophomore year, she practically lived in my dorm, never a night going by we didn't have sex. Even if she was on her period, she was horny, insisting that I let her blow me or fuck her up the ass.

Oh, yeah. The finger from our first night together was just a preview. The girl loved anal, cumming harder from it than anything else. We had a separate budget just for lube, and I found out that her wearing a butt plug was by no means a rare event. She was easily the most skilled woman I'd ever been with when it came to sex and sexuality.

On the holidays, she'd normally go home to her family, but she'd also come to see my family as well. Everyone in my family adored her and thought I'd found an absolute perfect match for me. They didn't even object when we got our own apartment junior year, making me pretty domesticated at the age of 20.

Only one thing concerned me with Beth. She'd never invited me to meet her family. She'd make excuses like they were out of town or 'it wasn't the right time'. I had no doubt that she loved me and wanted to be with me, but she kept her family at arm's length for some reason.

That was until we were beginning to plan our spring break, thinking of taking her to the Cayman Islands so we could truly relax. That's when she hit me with it.

"So, I wanna talk to you about spring break," Beth said, sitting at our kitchen bar in the apartment.

"Ok," I replied while eating my cereal. While I was hoping for a tropical retreat, I was open to suggestion.

"I know you were thinking of us going somewhere tropical or a beach or something."

"I was," I admitted, "you in a bikini is always a plus." She blushed a bit while jiggling her tits a bit.

"It's not like you don't get to see me naked," Beth said giggling. I just shrugged and continued eating. "No, I was thinking about going somewhere else."

"Ok, I said, open to other ideas, "where are you thinking?"

"Home," she said reservedly. I almost dropped my spoon.

"You wanna go to your parents instead of spending spring break with me?" I asked, both confused and a bit hurt. "I thought you wanted to spend it together?"

"I do," she said reaching for my hand. "I want you to come with me."

This time, I did drop my spoon. After two years, she wanted me to meet her parents. I was dumbfounded.

"What changed your mind?" I asked.

"Babe, it's not that I didn't want you to meet them," she tried to explain.

"Could've fooled me..." I said with heavy sarcasm. While we'd always gotten along great, this had been a source of friction with us, me not at all understanding why she didn't want her parents to meet me. I'd taken the position that she was ashamed of me somehow, me eventually learning her parents were wealthy. She said repeatedly that it wasn't that at all, almost crying whenever I'd suggested that.

"Ted, I know," she said, clearly getting why I'd make that remark. "I know that I've kept my family at arm's length when it came to you. Like I told you, it had nothing to do with you. I love you with all my heart."

I could tell from the sound of her voice that she meant it when she said that she loved me.

"So, why now?" I asked.

"Because it's time," she said resolutely. "We're gonna be graduating soon and starting our lives. You should meet them."

While we weren't engaged, we had already decided that we'd look for job opportunities in the same places, not wanting to separate or be long-distance.

"Will you come with me?" she asked, looking nervous.

"Of course, I will," I told her, pulling her in close to me, "I love you, Beth. I just wanted to get to know you're family, especially if someday, they might be mine as well."

"Ok," she said, sounding relieved, but also still nervous. "I'll tell them we'll both come. But there's a few other things too."

"What?" I said, wondering if she was gonna back out now.

"Well, you know my family has money, right?"

"Yeah..." I told her, wondering where she was going with this. Beth had told me about her family's money after our first month of dating and it had never really come up again.

"Well, if you come with me," she said, almost fidgeting, "they're gonna want you to fill out an NDA."

"An NDA?" I asked puzzled, "a non-disclosure agreement?"

"Yeah," she said, almost embarrassed that she had to bring it up. "They require it of anyone that goes to their house. Lawyers..."

"So basically, I can't tell anyone I met your parents?" I asked still confused.

"No, of course you can," Beth replied. "You just wouldn't be able to talk about the family or anything."

"That's a little strange," I replied.

"I know," Beth said exasperated, not at me but seemingly toward her parents. "This is one of the reasons I put this off. Do you want me to cancel and we'll try it another time?"

AH HA! I thought in my mind. I figured this was her trying to wriggle out again of me meeting her family. I wasn't gonna take the bait.

"No," I told her. "No, I'll sign it."

"Are you sure?" she asked, a bit surprised.

"Sure, why not?" I told her. "I guess it's not really that big a deal. Eccentric, maybe, but whatever."

"Ok," she said, still somewhat surprised. "I'll let them know."

And that's how I wound up in the back of a luxury SUV on our way to the airport.

I'd signed the NDA a few weeks back, a friend of mine in the law department looking it over, just to be safe. He said that he didn't see anything strange in it but said to be sure not to break it. This guy came from money too and I asked if this was typical of people from rich families. He told me that he wouldn't say typical, but certainly not unheard of.

Once Beth told her family we were coming, I asked where it was we were actually going. She said her family had a private compound in New England.

"Like the Bush family?" I asked, remembering Kennebunkport.

"Sorta," she said in a weird tone.

Instead of us flying on a commercial flight to Logan, I was surprised again when we went to a private airstrip near the school and a G7 jet was waiting for us. I looked at Beth more than a little stunned. She just shrugged and giggled nervously.

"I may have underrepresented how wealthy the family is," she admitted.

"Ya think?" I told her as we got out of the car. As soon as I got our bags from my trunk the guy who was standing by the plane came over.

"Good to see you again, Miss Beth," he said in greeting.

"You too, Kenny,"

"And you must be Mister Ted," he said grabbing our bags from me.

"No, I'm just Ted," I told him jovially, but also in a way that told him not to pull the mister stuff with me. I've never liked formality much, not even in classes when I was called Mister. Maybe this is why Beth had been keeping her family from me, I pondered.

We got on the plane and found everything was beyond regal. Large leather seats, full bar, TVs, everything. We got in two of the seats and strapped in. A women came from the back and offered us Dom Perignon champagne.

"Your parents wanted to celebrate your coming home," the woman told Beth. "And of course bringing your boyfriend home finally. Enjoy!"

"Thanks, Petra," she said taking the glasses.

"Our flight time will be one hour and twenty minutes," Kenny informed us from the cockpit. "Sit back and relax, kids," he said while powering up the engines.

"It was nice of your parents to offer us champagne," I told Beth, taking my first sip of expensive alcohol. "I guess they don't mind me coming."

"Yeah," she said rubbing the back of her neck a little. "They're good at small gestures like that."

My first flight on a private plane was amazing. We watched TV, had a few drinks and snacks, and just enjoyed the time in the air. I was almost sad when we landed, wishing the flight could've been longer.

When Kenny opened the hatch, I was surprised to find not an airport, but more of a private airstrip. I saw a hanger with other planes and a few helicopters as well.

"Beth," I asked standing at the top of the plane's stairs, "is it possible that your family has its own air force?" I asked in jest, but not entirely.

"Well..." she said somewhat embarrassed, acknowledging the weirdness of the situation. Just then, a Cadillac Escalade pulled up and a woman got out of it.

"Beth!" she said waiving to her.

"Lainey!" Beth said running into the girls' arms.

"It's so good to have you home!" she said releasing my girlfriend finally. "And this must be him," she said looking at me.

"Lainey, meet Ted," Beth said in introduction. "Ted, this is Lainey, the family's best driver."

"Nice to meet you," I said extending my hand. She brushed it off and offered a hug instead.

"Very nice to meet you, Ted. Beth's told us so much about you."

"Nice to hear," I said as she released me. By then, Kenny had our bags in the back of the SUV.

"Come on," Lainey said, opening up the SUV doors, "everyone's waiting for you two. "You're the last to arrive."

We climbed inside the car and found it was also luxurious and tricked out. Touchscreen panels, computers, the works. I also saw some bottles of mineral water.

"Lainey?" I asked as she got into the driver's seat. "Mind if I steal a bottle of water back here?" She wasn't quite giggling, more chortling.

"Of course," she said, trying to conceal her amusement. "That's what it's for."

"Would you like one?" I asked her.

"I'm good," she said waiving her arm, "but thank you. You were right, Beth, he is polite."

"That's my man," Beth said, hugging my arm.

"So, how long till we get to the "compound"?" I asked either woman. Again, Lainey chuckled at me.

"This is all part of the compound," Lainey explained, causing me to look around all the woods in astonishment. "But if you mean the main house, we'll be there in about five minutes. Normally, it takes ten, but I drive fast."

"She really does," Beth said laughing.

"That explains all the speeding tickets you get," I told Beth, ribbing her. Lainey burst out laughing now.

"Oh yeah," Lainey said through the laughter, "I pretty much taught her how to drive so she developed a lead foot."

We continued chatting until I saw the first signs of the house. It was massive! Three stories at least, massive outdoor patios on every level. Perfect landscaping, and a beautiful view of the Atlantic. Lainey pulled up to the front door of the mansion.

"Thanks for the ride," I told Lainey.

"You bet!" she said as she got out and opened the door for us.

As soon as she did that, the mansion doors opened. I then saw six people standing in the doorway, undoubtedly, her family.

"Beth!" the older woman yelled.

"Mommy!" Beth said rushing to her. Soon, she was hugging all her family members while I just stood there looking them over. It was an awkward thirty seconds as I was basically just the guy with the bags.

Eventually, Beth separated from her family and came over to me.

"Guys, this is Ted," she said presenting me to her assembled family. They then lined up to greet me.

"Nice to finally meet you, Ted," her father George said coming over to me. His 6'2" frame wrapping me in a hug, which surprised me. For a man in his mid 40's he looked surprisingly youthful, not a grey hair on his head.

"Ted, welcome to our home!" her mother Cecilia said in greeting me with another hug. Her dark blonde hair was a contrast to her redheaded daughter, but one thing that was similar to her daughter was her breasts. Had to be at least DDs that she squished up against me. She even gave me a peck on the cheek.

"Beth, his pictures do not do him justice," was the response of her oldest sister, Diana. Blonde haired, similar in height to Beth with C-cups sitting proudly in her polo shirt as she hugged me as well.

"Good to meet you," her older brother Richard greeted me, surprisingly again in another hug. He looked like a younger clone of his father, so much so that I wouldn't've been surprised if the two were confused for each other at times.

"Hi, Ted," Annie said in greeting me with yet another hug. Beth's sister right behind her in age, she was the only other one in the family with red hair, longer than her sister's flowing down to a pair of breasts just slightly less full than Beth's.

"It's about time we got you here!" Beth's youngest sister Hannah said greeting me. Her blonde hair flew in every direction as she hugged me as well. She had a tight, athletic body, while maybe not as gifted in curves as the rest of her family, she was also the youngest at barely 19.

"That's quite a welcome!" I said, slightly overwhelmed by the affection. I guess in my mind, I was prepared for a stiff and stolid greeting. This was clearly not the family I was expecting. "It's nice to meet all of you."

"It's long overdue," Cecilia said coming back up to me. "We've been telling Beth for a while now to bring you out."

I quickly shot a look at Beth who had an almost guilty look on her face. So, it was Beth that was behind me not meeting her family. I knew that was gonna be a conversation, but George quickly got my attention.

"Come on inside," he said putting an arm on my shoulder as we were led inside.

I walked into a huge front room. It wasn't marble floors or anything, but it was clearly professionally decorated and adorned.

"You have an amazing house, Mrs. *******," I told her. (NDA remember?)

"Oh, please Ted, call me Cecilia," she said warmly. "No need to be formal with us."

"We're very open here," George said in a similarly warm tone. Beth started coughing when he said that. I made sure she was ok before we continued on the tour.

They showed me all around the house, kitchen, patio, pool, hot tub, everything. It all looked pristine, like it'd just been shown in a magazine. We eventually went upstairs and they showed me Beth's room.

"Well, here you go," George said as he showed us in. It was a large room with a walk-in closet and a makeup station. Not to mention a king-sized bed. I saw our bags there and was a little surprised, having been fully prepared to me forced to sleep in another room.

"You guys get settled in and meet us on the patio," Cecilia suggested. I noticed that everyone kept telling Beth as they left how happy they were that she was home and the girls all saying they were happy she finally brought me. I didn't engage with Beth, until they all left and were out of earshot.

"So, they wanted me to come?" I asked, trying to mask my anger.

"Babe, listen," Beth said trying to get me calm, "I'm sorry. I get nervous when it deals with my family."

"Why?" I said almost incredulously, "they seem really nice. I thought you liked your family."

"I do," she said quickly, "I love my family, but they can be a lot."

"Why were you so scared for me to meet them?" I asked flat out. "What is it about me you think they won't like?"

"No, no," Beth said, now wrapping her arms around me. "Ted, I love you so much. I promise, it had nothing to do with you. I just worry."

"Worry about what?" I said, softening a bit in the warmth of her hug.

"My family is different than most," she said. "I worry."

"Why? Cause they're rich?" I asked, kinda confused. "They certainly seem normal enough."

"Yeah," she said with a weary tone. "You may change your mind on that."

"Look," I said breaking the hug but still holding on to her. "I love you, you know that. If your family is odd, we'll deal with it. I'm not worried."

She clearly was though, as she gripped me harder.

"Are you sure?" Beth asked with enough fear to make me giggle.

"Yes, babe," I said, putting my forehead to hers. "It'll be fine."

Beth hugged me tight again as we unpacked. Beth suggested we change out of our travel clothes so I put on a polo and shorts while she wore a sundress.

"Whoa," I said looking at her after she changed. She was wearing a sundress that showed a generous amount of cleavage and made it clear she wasn't wearing a bra.

"You like?" she asked, twirling around to show off all her angles.

"Obviously," I told her, still transfixed. "Is it a little provocative for your family, though?"

"I doubt it," she said confidently. "I think they'll like it."

I shrugged, feeling that obviously she knew her family better than I did. She gave me a kiss and let me out to the patio. When we stepped out, I saw that everyone else had changed as well. George and Richard were dressed fairly similar to me, but it was the women that caught my eye.

Cecilia was wearing a sundress much like Beth's, her ample cleavage out for anyone to view. Diana and Annie were wearing crop tops and short shorts. Hannah was wearing yoga pants and a tube top, her taught stomach on full display. I guessed that Beth had been correct about her assessment of her family's clothing attitudes.