Chapter 1: Lisa
It was a beautiful summer evening in Cincinnati. I was really enjoying my new obsession of cycling and was all set to put twenty miles in to get me more than halfway to my weekly hundred miles goal. I’d been divorced for about a year and had just finished my angry dating period. A series of one night stands and two ongoing friends with benefits were starting to wear on me so I swore off women for a while and started focusing on myself. I didn’t have my kids as often as I would like, so I was trying to fill the time with healthier alternatives than going to bars.
I am 6’4” and 245 pounds. I was in the military after high school and kept my physique pretty much intact. I went to college in New England where I met the mother of my children, and moved to KY five years ago for a great job as an executive at a nearby company.
As I was loading the bike on the back of the truck, my buddy Mike called asking me to be his wingman that night. “Hey Steve, I need your help tonight. I am going to the waterfront concert to meet a 28-year-old redhead.” Mike was 38.
“Dude, I was just heading out for a ride. What time is this meet supposed to happen?” I asked
“Six-thirty. My ex-girlfriend set it up. She is a friend of hers.”
This got my interest. After the obvious questions, he explained to me that he’d dated this now ex-girlfriend a couple of times before they mutually decided that they were not compatible. So, Mike being Mike, he asked her to be his wingman when he went to bars to prowl for easy pussy. She apparently agreed to the scenario a few times and then stopped doing it. I didn’t ask why but probably because of the overall awkwardness of the situation. Instead, she agreed to introduce him to some of her single friends. Now Mike needed me there to occupy his ex while he made his moves on her friend.
I reluctantly decided to bail on my ride and go. I really wasn’t interested in meeting anyone but the bands were pretty good and he was buying the beer. So…
Mike introduced me to Lisa and I immediately saw why it didn’t work out between them. Mike is particular about a woman’s ass. If it isn’t big, he isn’t interested and he especially likes Latino women with big asses. Lisa had a nice tight slender ass and was not Latino.
While Lisa and I watched our friends start the dating ritual, we both knew within a few minutes that they were not going to hit it off. Mike was more traditional where the women needed to be home, barefoot and pregnant. Lisa’s friend was much more independent and, at age twenty-eight and a fiery redhead with matching personality, she was much more mature than Mike. It was funny watching the two battle back and forth.
Lisa provided some cutting play-by-play comments and showed me some of her wicked sense of humor. We lost interest in the battle going on and started talking to each other and soon we were hitting it off pretty good. I looked at her more closely. She was fit (I later found out that it was from years of Yoga) about 5’4”. Nice C-cup breasts fit her form perfectly and incredible brown eyes sparkled every time she smiled. When she stood up I could see the most amazing pair of long sexy legs. I am not a leg guy, so it was unusual for me to zero in on that. She was wearing a skirt, but I could see a slender athlete’s ass, which was fine by me.
As with most divorced people when dating, we talked about our exs to let the other person know what mistakes were made and provide good examples of what we want and don’t want in a relationship going forward. Basically an interview.
As we talked, we lost track of everything. Our friends ended up leaving and we stayed until the live concert ended. Then we went to a blues club and talked some more over a couple of drinks.
I found out that she and I divorced almost at the same time. Her triplets and my twins were the same age and we each had an older kid. She was a part-time schoolteacher working with special education. I was an executive at a large company in town.
Lisa was from the area. Her family was close-knit, much like mine. She had two sisters and her Dad helped take care of her after her husband of twelve years left her for another woman while she was pregnant with her triplets. Total dick move. She was devastated when she found out about the cheating. I could tell she really loved him, but it was not reciprocated.
My divorce wasn’t due to cheating. I was just tired of her bitching, lack of sex, and general non-support. She was great with the kids, but I had not felt love or even like for her in years. My family all told me after the fact that they never liked her. Could have used that advice twelve years earlier, but it is what it is. I love my kids and wouldn’t trade them for anything.
That night (really it was one-thirty in the morning) I walked her to her car and we kissed good night. It blew my socks off. It was one of those incredible first kisses that you remember for a long, long time. We made a date for the next Friday night.
The kids were with our respective exs so we decided on a movie at my place. Her idea. I was trying to be a gentleman, suggesting dinner and a comedy show somewhere else. I am like a lot of men and don’t take hints very well and this was a blatant enough hint that even I could get it. Needless to say I was really looking forward to Friday night.
When Friday night arrived she lightly knocked at the door to my bachelor apartment. When I opened the door I was greeted by that gorgeous but nervous smile. Lisa had on a cute sundress that showed the tone in her arms and the beautiful legs I remembered from our first meeting. I gave her an awkward hug in the doorway, invited her in and asked if she wanted some wine.
She followed me into the kitchen. I got the bottle out of the rack on the counter and turned around. She moved up close to me and I just could not help but stare deeply into those beautiful brown eyes. A split second later I put the wine on the table and forcefully took her face in my hands and kissed her passionately. For several minutes we stood there kissing. She started pushing her tits into my lower chest and squeezing me as she moved her hands all over my back. I had a raging hard-on in no time. We left the wine and the unwatched movie and kissed our way into the bedroom, occasionally bouncing off a wall on the way.
Once in the dimly lit bedroom, she had my shirt off and then sat on the end of the bed to start unbuckling my belt. She was looking straight at the tent I had in my pants. As soon as my dick came into the light I heard a gasp and a “Wow!” as she reached for it. She took my eight and a half inches in her hand and stroked it the or three times. I pulled her to her feet and unzipped the dress and removed the bra in quick succession. She kept hold of my cock while I undressed her.
She knelt before me and took my cock in her mouth. Her blowjob skills were okay. Not great, but God it felt good. I stared at her swaying c-cup breasts with quarter size areolas and pencil eraser nipples standing at full attention.
After a little while she kissed her way up my body and into a full embrace. I slid her panties over that perfect ass and amazing legs and laid her gently back on the bed. I started to kiss down her body, a dart of a soft tongue followed by a sensuous little suck with my lips. I got to her tits and she stopped me there.
“Fuck me now,” she said.
I quickly picked her up off of the bed and moved her up toward the pillows. As I placed her down while kissing her, she brought her legs up and I found her love hole quickly. This girl was literally hot. Her pussy was dripping wet. I got the head at the entrance and then slowly moved into her. I was in heaven.
“God you feel so good,” I told her. She moaned in return.
I finally got my cock all the way into her and could feel her cervix at the end of my cock. As I started moving in and out, she would jump everytime I bumped her there so I backed off a bit. We fucked missionary and then cowgirl. I was about to flip her over when she shuddered and screamed. Her pussy clamped down on my cock and I lost it. I had one of the best orgasms I had ever had. My legs started shaking and I let loose with rope after rope of cum deep into her pussy. She collapsed on my chest.
“I don’t normally do this,” she said while catching her breath.
“What?” I asked.
“Sleep with a guy on the first date,” she said.
She rolled off of me on to her side, releasing my softening cock from her pussy, and moved her head onto my shoulder and started caressing my chest. S gorgeous leg was strewn across my thighs.
“That was amazing,” she said. “I haven’t cum like that in years.”
“You have an amazing pussy,” I said with a smile. “When you tightened your pussy I just could not hold off any longer.”
She chuckled. “When I saw that thing, I wasn’t so sure…” she said as she lightly caressed my now flaccid cock. Her fingers touched it gingerly and felt the wetness that was our mutual cum. She raised her head and looked me in the eye. A sly grin came across her face.
“It’s such a mess down there,“ she said as she raised herself up and then moved down the bed. She slowly lowered her face to my cock. She looked up at me when she was close. “Needs a little cleaning,” she said in a hoarse whisper and took my cock into her mouth. My cock quickly came to life as she licked all around the base and my balls and took the shaft in her mouth again. She gripped the base of my cock and started stroking, keeping pace with her mouth.
My cock is always sensitive after sex and I started feeling that tickle sensation in the head of my cock. The kind where it borders on too intense and pleasurable. Soon she had me ready to pop…
“I’m going to cum,” I said.
She looked up at me with those gorgeous brown eyes of hers and moved her mouth up to the top of my cock and left her lips wrapped around the head while she continued to stroke it.
I put my head back on the pillow and came in her mouth. I could feel her swallowing quickly. A little leaked out of the corner of her mouth, but after the spurting subsided she found the droplet with her tongue.
“Wow!” I said. “Amazing. You are incredible.”
“I needed that,” she said as she crawled up the bed to start snuggling again.
“What, cum?” I asked.
She laughed, “Yes but no… I needed a real cock and everything that comes with it. It has been a long time since I have made love to a real man. The last few guys I dated were all shorter and definitely smaller, ” she said referring to my cock.
We talked for a while and made bathroom breaks. I got up to retrieve the wine and bring it into the bedroom with a couple of glasses. After an hour or so of talking, I started feeling more and more attracted to her by each passing minute. She was smart and funny. She was also quiet and meek at times. When we start talking about the exs again, the hurt and fragility were clearly visible on her face. I just wanted to wrap her up in a big hug and never let go.
As we talked by the light of the tv screen and sipped wine I started running my hand over her body. I came to her stomach and she quickly grabbed my hand.
“What?” I asked. “Is something wrong?”
She sighed and then pushed the covers back. She had stretch marks on her otherwise flat stomach. “My kids and I call it my elephant skin,” she said looking at me for a reaction.
“Sweetie, you are five foot four and a hundred pounds soaking wet and carried triplets to term.” I said. “I think you are amazing and this…” I reached over and rubbed her belly, “is part of who you are. And I am really liking who you are. Every bit of you.”
She reached over and kissed me gently and looked into my eyes as if to make sure I was serious about what I just told her. “Is that why you wouldn’t let me eat your pussy?” I asked with a smile.
She laughed. “Yes it is.”
“I just wanted to make sure it wasn’t a preference. Some girls don’t like it…”
“Oh, I am not one of those girls. My ex would never do it and the last few guys I had been with weren’t very good at it.”
As with any guy with an ego, I took that as a personal challenge. “I love eating pussy. I love the way it feels and tastes and I’m told I am prety good at it. “ I started moving down toward her cunt.
This was the first time I got a good look at the lushous folds that treated my cock so well a little while ago. She had these puffy outer labia that looked amazing. Her inner labia were rather large and sexy. There was a little landing strip on top of her mound. As I kissed around the area I got to take it all in. I was not joking, I truly love eating pussy.
Our eyes locked as I got closer to her pussy. I stuck my tongue out and flicked her clit a little bit. She rolled her head back with a moan and closed her eyes briefly.
I went right to work. I kissed her outer lips gently and then licked straight up her slit from the bottom right to her clit. I put my mouth over her little nub and started licking it gently. She started moving like it was uncomfortable. I changed tactics and flattened my tongue on her clit and put more pressure on it. That did the trick. She let out a long moan.
“That’s it,” she whispered.
I lowered my face down and started tongue fucking her opening. She tasted wonderful. Sweet and salty and so wet. I moved back up to her clit and added a finger. I curved it up toward the g-spot area and quickly found it as her reaction was almost as if she just received an electrical shock. As I started playing with it, Lisa’s hips started to gyrate. I knew from experience that the key was rhythm. I would keep the same tongue movement on her clit and finger movement on her g-spot and keep the same pace and sure enough, she had a nice long cum. I instantly felt more wetness coming from her hole and moved my face down to lap up as much as I could.
After a minute or so of recovery, she sat up and grabbed my face on either side of my head and coaxed me up for a kiss.
“Thank you. You were not bragging. You know what you are doing down there.”
“Thank you. I enjoyed your pussy very much.”
We talked a little bit more and then fucked one more time before she had to leave. We set another date for the next night.
