Gypsy Love

I was a socially awkward, yet decent looking and certainly smart, guy who wanted nothing more – aside from making money – than to have a family with a bunch of kids. I guess that was due to the loveless family that I grew up in. My parents were cold people, and I was an only child. I always considered my life shitty compared to some of our neighbors with three to five kids in the families, and parents that seemed to be concerned about them and always doing things with them.

While being socially awkward may be a real drawback in some professions, in mine – computer security – it was not. Once I got a B. S. in Computer Engineering and subsequently got a professional certificate in advanced computer security, with an inheritance from my parents' death in a car accident when I was in college, I started my own computer security business. By the time of my twenty eighth birthday I had a good business and was making lots of money. I used some of the money to buy a cabin in the woods, some to buy a nice ranch house with five big bedrooms, and some to buy a nice car.

Despite my wealth I was still only in the dreaming stage of my desire for a family with lots of little kids.

Then I ran into Aishe.

Actually, it was more like Aishe ran into me.

I was strolling through an open air market one Saturday when I got jostled by an exotic looking young woman in a flowing skirt and flowery blouse. "Excuse me," she said with a smile.

"Pardon me" I replied, not used to exotic women talking to me, even if it was just two words.

I had gone only another leisurely twenty paces or so when a muscular man with a fanny pack and a buzz cut stopped me. "Mr. Watkins," he said reading from an open wallet that looked suspiciously like mine.

"Yes..." I hesitantly replied.

"I'm police officer Rollins. We caught this woman," he said motioning to the exotic woman who had run into me standing near my left side, obviously in handcuffs and held stationary by a big guy who looked just like Officer Rollins only he was black instead of white, "pickpocketing your wallet. I believe this is it, isn't it?" he continued, holding out the wallet for me to see.

"Yes, it is," I replied once my surprise was overcome, and I instinctively reached for it.

"Sorry," Officer Rollins replied pulling his hand back. "We can't let you have it back until we dust it for prints since even though Officer Jenkins and I witnessed the act, these days we like to have forensic evidence as well just to be safe. You can either accompany or follow us to the station."

"Can I at least have my driver's license in case we get separated and I get pulled over by one of your brethren?" I asked.

"Sure," Rollins said with a smile as with his latex-gloved left hand he pulled the license from my wallet and handed it to me. "The station is on 4th and Maple – actually there is no reason for you to follow us there, you know where that is, don't you?"

"Yes, I do. I'll get my car and meet you there."

The exotic woman did not seem happy as she was led away by Jenkins – but there was something about her look that really intrigued me. When despite her otherwise dour expression she turned, smiled, and said "Sorry" staring into my eyes with her big brown doe-like ones, I was smitten.

At the station the exotic woman – who I found out was named Aishe Loveridge – was booked, her prints lifted off my wallet, and it was returned to me. I was curious that she smiled at me again in the police station.

"What's going to happen to Ms. Loveridge?" I asked.

"She'll have a bond hearing before a magistrate at 5 p. m. and then will be put in jail for the rest of the weekend if no one posts her bond, which is the likely scenario even if she gets a call to her family," Rollins told me. It was about 2:15 p. m. then.

As I walked out of the police station I got one more smile from Aishe as I went past her. I was smitten again.

I went back to the open air market, but my mind was not concentrating on the wares for sale, but rather was playing ping pong. "She's a common thief – get her out of your head;" "She's obviously interested in you or she wouldn't have smiled at you three times, or said sorry;" "The last thing that you need is to befriend a criminal;" "She's better looking than any other woman who's ever smiled at you in your life;" were some of the shots being bandied back and forth in my overworked brain. Finally I came to a temporary conclusion – I'd go to her bail hearing and play it by ear.

Rollins and Jenkins were nowhere to be found at the police station, but the booking officer, Geraldine Smith, recognized me and was a little surprised to see me when I arrived there about 4:45. "Where is the bond hearing for Ms. Loveridge?" I asked Officer Smith.

"Down this corridor to the end," Geraldine said pointing to her right, "then turn left – you can't miss it. Why do you want to know?"

"I...I...well, I might want to bail her out," I stammered.

"She's Roma you know," Smith sternly said. I didn't really understand what that meant. I thought that it might be some sort of classification of thieves; I had lived a sheltered life and didn't know that "Roma" is what gypsies call themselves.

I just nodded my head and said "I'll be careful;" fateful words!

I sat near the front – the bond hearing was held in what appeared to be a small – very small – courtroom. Aishe was led in with five other women, and about ten men were led in separately. Aishe saw me in the second row of what were just like church pews, reserved for spectators, and smiled again and even gave me a little wave. "Wow she's got a nice smile," I mumbled to myself as I gulped.

Aishe was the third person up. There was one female public defender for all of the incarcerated, who really had nothing specific to say about any of her "clients." After the Magistrate set Aishe's bail at $1,000 cash or bond I rose to my feet and spoke – something entirely out of character for me.

"Mr. Magistrate...uh, Your Honor," I choked out. "Where can I post the bond for Ms. Loveridge?"

He gave me a strange look, like either I was stupid or no one had ever asked him that question before. "At the front desk – bailiff bring Ms. Loveridge to the front desk."

Aishe's smile lit up the entire room.

I followed behind Aishe and the bailiff as he led her down the aisle of the hearing room toward the front desk. "She has a nice ass," I said to myself a number of times before we reached Officer Smith again.

Smith was shaking her head as she looked at me while Aishe and I filled out the necessary forms and I handed Smith a credit card that would be charged $1,000 for the bail money. When we were given the date of Aishe's next hearing and everything was completed Aishe and I walked out of the police station together.

"That was very nice of you, Mr. Watkins, especially after it was me that lifted your wallet," she said with that million dollar smile, while touching my arm. "Why did you do it?"

"Please call me Jerry, Aishe – and if you'll come to dinner with me – and promise not to lift my wallet again," I said with my own smile, "I'll tell you."

"Sure," she replied. "Can I use your cell phone to call my mama first, though?"

"Of course," I responded, handing it to her.

She went off to the side a little and talked in hushed tones, terminated the call and handed the phone back to me. "Where should we go for dinner?" she asked.

"Do you like French food?" I asked.

"Yes, what little of it I've had."

"Well there's a nice country French bistro about a mile from here – let's go to my car."

My "date" with Aishe was the only one in my life that I wasn't overcome with anxiety about probably for three reasons: 1) it was spur of the moment; 2) I had just done her a real solid by bailing her out; and 3) there was something about her smile that made me mellow.

Despite the fact that Aishe was obviously not highly educated, she was exceedingly interesting. She had no pretense, including eating her food like a starving truck driver. Our meal lasted two hours and it seemed like ten minutes; I was fascinated as well as smitten.

When we left the restaurant as I held the car door for her she sauntered up to me. "You're a real gentleman, aren't you Jerry?" she said as she put her arms around my neck. I tried to stutter something out, but didn't make it before her lips were pressed against mine. They were so soft – God they felt good!

Aishe finally broke it off, smiled again, and slithered into the front passenger's seat. When I entered the driver's seat and put my seat belt on she handed me my wallet and giggled "Apparently I'm going to have to teach you how not to get pickpocketed."

I'm sure that I blushed. "I guess so," I chuckled. Actually since all of my blood had rushed to my dick while she was kissing me it was no wonder that my brain didn't know that I was being pickpocketed.

I drove Aishe to the trailer park that she lived in. She seemed to have no embarrassment about it. "Come in and meet my family," she said when we arrived.

No woman had ever asked me to meet her family before.

Inside a single wide trailer were three other women and a small child – maybe two years old.

"Family, I'd like you to meet Jerry Watkins," Aishe opened with a smile. "He's the nicest mark in the history of thievery," she chuckled. The three women looked shocked for a second, and then laughed.

"Jerry, this is my mother Florica," she started out introducing me to a woman that for all the world looked exactly like I would picture Aishe looking in twenty years, with the same exotic face, slim body, and ample breasts that Aishe had. I kissed Florica's hand while I said "Don't tease me, Aishe, I know that this is your sister not your mother," getting a chuckle from all four women.

"No, Jerry, this is my sister Jaelle who is a year younger than I am and lives with my Mom and me," Aishe continued pointing to the youngest woman there, probably eighteen or nineteen since I had found out that Aishe was twenty, "and this is my married sister Lala Doe and her little girl Mala, who are visiting," Aishe continued pointing to a woman probably three years older than Aishe who was holding the little girl's hand.

"Pleased to meet you," I said, kissing each adult's hand in turn and waving to Mala.

Both sisters were as exotic as Aishe, only Lala was significantly bigger and Jaelle significantly smaller that Aishe; all had similar facial features and bodies. In fact the size discrepancies among the sisters were really dramatic. Jaelle was five feet tall, or shorter; Aishe was about five feet four inches, Florica was about five feet six inches, and Lala was about five feet eleven inches. I found out much later that it was because all the sisters had different fathers, although because they all looked like the mother no one would ever figure that out just by observing them.

I actually stayed and chatted with Aishe's family for an hour. Like Aishe all were uneducated but very interesting. I found that Lala lived with her husband in a trailer a few down from Aishe's and that all had just recently moved to the area. When I got up to leave Aishe went outside with me. "Thank you again for your kindness, Jerry. You might have to come with me to the hearing in a month, though, otherwise I'll end up in jail – and I think that you might like it better if I was free," she said in a sultry voice as she snuggled up to me and kissed me on the lips.

Once she broke our kiss I stared into her smiling face. "Uh, sure I'll help. Can you go out on a date with me next week."

"Any night except Wednesday," she said with a lilt in her voice.

"Uh, how about Thursday?" I asked.

"What time?" she inquired giving me another quick kiss on the lips.

"Six o'clock OK?"

"I'll be counting the minutes," she chuckled, and then went back into the trailer after giving me one more kiss.

My mind was in turmoil as I drove home. Aishe was not only the most colorful woman that I had ever met in my life, but she was so damn sexy. I had a partial hard on most of the night.

While I was not a virgin, I also was not experienced. Believing that study was important for any activity on Sunday I found a high end call girl through a friend of mine. Her name was Dawn; she came to my house about 6:00 p.m.

I was impressed not only with Dawn's looks, but with her poise. In a halting stutter – which she got me through by holding my hands – I told her about my fascination with Aishe and not wanting to be a clown if my relationship developed into a sexual one. "I wonder if you could help me get more comfortable with the female body so that I'm not clumsy if I'm lucky enough to get a chance to have sex with her."

Dawn chuckled, then got a glint in her eye. "No problem, Jerry. First you're going to take my clothes off, then I'll take yours off, then you'll pleasure me orally, I'll pleasure you orally, and then will have sex rotating between positions."

I gulped as she ran her hand over my chest and down to my crotch. When it got there I got an instant full hard-on. Dawn got a surprised expression on her face and said "Whoa, dude. Do you have some serious meat there?"

I gulped again. The only two girls I had ever fucked were "large" women – in fact very large women – who made some passing comment about my equipment but didn't fawn over it. "I don't know," was my honest answer to Dawn's question.

She fished out my cock, smiled, and said "Aishe will love this hunk of meat, Jerry, I assure you. It's nice and fat with a nice aspect ratio besides; it fact it may be the fattest cock I've ever seen live. I'm gonna have some fun myself tonight."

To say that I learned a lot that night would be the understatement of the decade. To say that I enjoyed myself would be almost as big of an understatement. Dawn told me that she never, ever stays past the time she's been paid for, but I got almost four hours of her time for three paid hours ($500/hr. and worth every penny), and we fucked – with a condom – three times in addition to my instruction on eating pussy.

I couldn't believe the confidence that my session with Dawn gave me. When I picked Aishe up on Thursday night her mother Florica and sister Jaelle were very friendly. Aishe held my arm as we walked from her trailer to the car. Aishe was bubbly the entire night as we went to dinner, went bowling, and played pool. The night ended when we took a walk in the park and kissed passionately on a bench for a good ten minutes before going home. When I dropped Aishe off with another passionate kiss and a promise to go out Saturday I could see her mother and sister peeking out a window with smiles on their faces.

When Aishe and I went out Saturday she insisted on coming to my place and making me a meal. We stopped at the store and got cabbage, beef, paprika, and rice so that Aishe could make me Sarma, a dish that she said was one of her family's favorites. When we got to my house I thought that Aishe's eyes would pop out of her head.

"Wow – this is the biggest, nicest house I've ever seen," she must have said five times as I took her on a quick tour. Then she got to work making Sarma and I helped as much as she would let me. We shared a bottle of red wine from my wine cellar with dinner. Although I didn't particularly like the smell of the Sarma when it was cooking, it turned out to be delicious, and Aishe gave me her trademarked brilliant smile when I complimented her on it.

After dinner we watched a movie for a while, as Aishe snuggled up closer and closer to me. Soon it was clear that she could care less about the movie as she started sticking her tongue in my ear and planting kisses on my neck. Thank God for Dawn's instruction. I stared into her eyes as she smiled and licked her lips, then I lay her on the couch and lifted up her skirt. She had no panties on, and a full bush crotch – unlike Dawn's shaved one. Undaunted by the hair I dove into her pussy with my tongue as I squeezed her sculptured thighs. Her clit was much bigger than Dawn's and easy to find and tongue or flick.

The woman went nuts; over-the-top flat out crazy nuts. She must have had an orgasm a minute, so many that it was just like one continuous one. When I finally came up for air, with her juices and hair on my lips, she moaned. "Do you have a condom Jerry; all the women in my family are allergic to birth control pills."

At Dawn's suggestion, on Friday I had purchased a Trojan Magnum Gold Collection with several different types of extra-large condoms. I quickly went into my bedroom and got them and when I returned Aishe was naked laying on couch cushions on the floor with her legs spread.

I almost came in my pants from the site of her glistening pussy, perky tits, slim waist, sculptured thighs, and "fuck me" expression. I dropped my drawers instantly, ripped open the condom that said "Magnum Thin" and quickly rolled it on. While I was doing that, however, Aishe's look changed. "My God, Jerry – your cock is so thick – I...I...don't know if I can take it." Apparently Aishe saw the distressed look on my face and brightened up as she smiled and said "But I want to try – however, I'll have to be on top."

So I lay down on the cushions and Aishe grabbed ahold of my condom-covered cock with her tiny hand and positioned her pussy over it. She slowly and carefully lowered herself onto me. "Holy shit you're thick," she moaned on several occasions. By twisting her body and pushing down at the same time, however, we finally got into a position where we could fuck – and fuck we did, although I let her control the tempo because otherwise I was afraid that I might hurt her. I came quickly, and hard – her pussy was much tighter than Dawn's – and she came shortly after I did.

When we disengaged and she lay her head on my shoulder I was in heaven. It was better than I thought it possibly could be, better than with Dawn because I had an emotional attachment. We chatted and kissed as we lay together, and massaged each other. I was getting hard again and could easily have gone another round but Aishe begged off saying that I had stretched her too much and she was too sore. However, she had no objection to a sixty nine and we both got each other off again in that position.

*****************

And so my relationship with Aishe Loveridge started in earnest. The first thing that I had to do, once it became sexual, was to be sure that she was kept out of jail. Therefore I hired her an excellent attorney and made it clear to the assistant D. A. that I personally did not want to press charges. The combination of the two got her a pleas bargain of six months' probation with no jail time, an entirely acceptable result.

Things moved quickly after that. I made it clear to Aishe that I wanted a big family, and she seemed entirely on board with it. She made it just as clear that if we lived together she wanted her mother and Jaelle to live with us in my large house; I had no objection to it since they always treated me well and were excellent eye candy. After negotiating a few more things, we got engaged to be married – and soon.

I was already in preparation for the marriage when John Tipton, the general manager of my company, took me aside. He was older than the rest of my employees – in his early fifties. Although he wasn't as up to date on the technology as the rest of us I had hired him because he had excellent business acumen and was a good manager and everyone who had ever dealt with him completely respected what he had to say. He had met Aishe and her family, and one Friday after everyone else had left the building he came into my office.

"Jerry, you know that I rarely give unsolicited advice. However I really care about you, and this company, so I'm going to. If you intend to marry Aishe – and her family – you're going to need an iron clad prenup."