I was looking for a new apartment. They had continued to raise the rent at my current place. In fact it had gone up almost 50% in 2 years. A new owner had purchased the apartment a few months after I had moved in. Although they had made a number of cosmetic “improvements”, painting, carpeting, hallway lighting, etc.; they had done little to truly upgrade or improve the apartments or the buildings. I had done some checking around and narrowed had my choices down to 3. I had already visited 2 of them and had an appointment at the third this afternoon.
I arrived a few minutes early. I walked into the office. It was nicely decorated and was very clean. There was a young lady sitting with her back toward me looking for something in a file cabinet. When she turned around I was pleasantly surprised. I recognized her immediately as my high school crush, Jessie.
I had had a crush on Jessie since the first time I had seen her during our sophomore year. She was a cheerleader for the football and hockey teams. Unfortunately I was a basketball player, so she never really noticed me and I was too shy to ask her out or even talk to her. During our senior year she was runner-up for homecoming queen. She was extremely popular and I was not. I had only seen her once since high school. At our 5-year reunion I worked up the courage to go and talk to her. She surprised me when we called me by name as I walked up to her. We had a short conversation, just small-talk. She soon was distracted by others and I walked away. On my way home I took off my nametag and wondered if that was how Jessie knew my name and who I was.
“Hi Ben. How are you doing?” she asked. “You’re here to look at an apartment, correct?”
I recovered from my surprise and managed to answer, “Yes!”
“It’s good to see you again!” she said.
“It’s good to see you again too!” I responded.
She grabbed a key and said, “Let’s go see the apartment.”
We walked out the door of the office after flipping the sign over to “BE BACK SOON”, then locked the door behind her. We walked across a circle to the building on the other side. We went inside and took the elevator to the 3rd floor. We turned left down the hallway. Whatever scent she was wearing filled the elevator. It smelled wonderful. I followed her noticing her hair. It was brown with blonde streaked highlights. I noticed her body. She was taller than average, maybe 5′ 9” or 5′ 10”. She had the curves of a woman with a great looking rear end. Her pantsuit fit her well, definitely flattered her figure. She stopped at the second to last apartment in the left side. She unlocked the door and we went in. The apartment was nice, though not much different than the others I had looked at earlier. I walked around. The walls had recently been painted and the carpet looked new.
Suddenly Jessie said, “You keep looking around. I have to go next door to my apartment and get something.”
Whether she knew it or not she just rented an apartment. It was “my dream come true” to be living next door to Jessie.
When she returned she asked, “What do you think?”
I pretended to think for awhile then said, “Yes, I am interested.”
“Would you like this apartment or one on a different floor?” Jessie asked. “First floor apartments are less expensive.”
“This apartment will be fine,” I responded.
“Sounds good,” she said, smiling that wonderful smile I remembered from high school.
Her face was so beautiful. Her glistening brown eyes, long eyelashes, perfectly shaped nose, full lips, and lightly tanned skin set her apart from almost every woman I had ever seen.
She walked toward the door and I followed. I again was mesmerized by her hips and butt. There was a slight bounce, but she was trim and well toned. Soon we were back in the office and I was busty completing the paperwork. I noticed her set down a doll and blanket on the file cabinet behind her desk. My heart sank. She had a child and was probably married or had a man in her life.
“What type of work do you do?” she asked in the melodious voice she had. (Can you tell I was still was enamored with her?)
“I am a computer programmer for a food wholesaler. I work with procurement, inventory control, and merchandising systems,” I answered. “Do you have a little girl?”
I pointed to the doll she had just set down.
“Yes. Emily. She is 7 years old. I have a date tonight and she wanted her doll to take to the babysitter’s apartment. One of the residents has a 15 year-old daughter that watches Emily for me after school,” she explained.
We had been out of high school only 8 years so she had her daughter soon after we graduated. I wondered who the father was but was afraid to ask her about it.
“Do you remember Tony?” Jessie asked.
I nodded. Tony was the best wide receiver on the high school football team. Then she just opened up and told me the whole story.
“Tony and I dated during the last part of our senior year and then into the Summer. He didn’t get any scholarship offers, so he had decided to join the Air Force. On his last night before leaving we had our last date. Things got very emotional and we went all the way. A couple of months later I realized I was pregnant. I wrote to Tony and then he called and I had the hard conversation with him. He wanted me to have an abortion. In other words he didn’t want to be a father or be responsible for a child. That told me all I wanted to know. I told him I was going to have the baby and he did not have to be a father in any way. I sensed the relief in his voice. Soon the call ended and I have not heard from him since. All my future plans changed. College and career were out of the question, at least in the short term. Next I had the hard conversation with my parents. They were disappointed, but very supportive. They agreed that because of Tony’s attitude that I didn’t want him in my or my baby’s lives. I lived with my parents for a few years until I got the job here as property manager,” she said and paused.
I could see tears in her eyes. I felt so sorry for her. I then noticed a couple of pictures on her desk. One was a picture of a baby. The other was a picture of Jessie and a young girl. Obviously it was her daughter. She was also very cute and looked very much like Jessie.
“She is very beautiful,” I said pointing to the picture.
“Thank you! I think so too,” she said.
I finished the paperwork. She took the paperwork and looked through it.
“So there will only be one tenant?” she asked.
“Yes,” I answered.
“I will get back to you after I get positive responses to your credit and background checks. When would you be looking to move in?” she asked.
“My current lease expires at the end of June, so July 1st,” I replied.
“I’ll start the lease for July 1st, but set the move-in date for Saturday June 28th,” she stated.
“Thanks! I hadn’t thought about the day of the week,” I said.
I thanked her again. We shook hands, the first time I had touched her. Her hand was soft and warm.
“I’ll get back to you in a couple of days when the reports come back,” Jessie said.
I turned to leave. Jessie’s daughter was getting off the school bus in front of the office. Jessie and I walked out together. Emily came running over and gave her mother a huge hug. Emily started talking a mile a minute telling her mom about her day. I waved goodbye, got in my car and left.
3 days later I received a call from Jessie. Everything had come back fine and she asked when I would like to come in to sign the lease. I tried not to sound too excited, but told her I would be there the next day.
When I arrived Jessie greeted me with a high smile. When I was about to sign the lease I noticed the lease amount was less than I expected. I asked about the amount. Jessie responded that she had given me the lease rate for a first floor apartment. I thanked her and completed the process. She surprised me by giving a hug before I left. Her hair and perfume smelled so wonderful.
A few weeks later I moved in on a Saturday. Emily was in the hallway watching as I was moving in. She was interested in and asked about every box and item as it went into the apartment. At lunch time Jessie came over from the office to get lunch for Emily.
“Do you want something for lunch? We are just having some sandwiches and fruit,” Jessie asked me.
“Yes, that would be very nice,” I quickly agreed.
Jessie’s apartment was the same layout, but was a mirror image of mine. Emily took my hand and led me over to a chair at the table. She was quite the little hostess. She put out the plates, bowls, cups, and silverware. She put a carton of milk and a pitcher of ice water on the table. Jessie finished making the sandwiches as Emily put a bowl of fruit on the table. They both sat down. Emily took half of a peanut butter and jelly sandwich. Jessie nodded to me to take what I wanted.
I took half of the ham and cheese, and half of the peanut butter. I wanted to leave Jessie her choice. She took the other half of the ham and cheese, and half of the cheese sandwiches.
“Emily doesn’t like ham and cheese sandwiches,” Jessie said.
“Yuch!” exclaimed Emily.
“She lives on peanut butter and jelly,” Jessie teased. “Please take some fruit.”
I spooned a few scoops of the fruit into my bowl and put the bowl of fruit in front of Emily.
“I don’t like pineapple either,” Emily said as she carefully selected her desired fruits from the bowl.
“Emily you should take at least one piece of pineapple. You’ll learn to like it,” Jessie insisted.
Emily made a face, bit slowly scooped one piece of pineapple into her bowl.
“I’m going to the bathroom. I want to see that pineapple gone when I come back,” Jessie said as she got up from the table.
When the bathroom door closed Emily put the pineapple on her spoon, but did not move it toward her mouth. I pushed my bowl closer to Emily’s and pointed at my bowl. Emily slowly lifted her spoon and moved it toward my bowl. She looked at me and I nodded. She put the pineapple in my bowl and giggled. Soon the bathroom door opened. Jessie came out to see both of us enjoying our fruit. As Jessie sat down Emily smiled a mischievous grin at her mom.
“Did Emily put the pineapple back in the fruit bowl?” Jessie asked me.
“No! She did not put the pineapple back in the fruit bowl,” I answered.
Out of the corner of my eye I could see Emily trying to keep a straight face. She took the other half of the peanut butter and jelly sandwich and began eating it to help her control her reaction.
“I injured my knee playing basketball in college and it hurts to bend down or kneel on the floor. Do you know someone that could help me put stuff away in the lower cabinets and storage areas?” I asked looking at Jessie.
“Me! Mommy can I help him? Please!” Emily begged.
Jessie looked my way with an “are you sure” expression. I nodded.
“Ok Em. Be sure to do what Ben tells you to do and the way he wants it done,” Jessie stated firmly.
“Yes, mom! I will!” Emily responded.
Jessie looked at the clock and said, “I have to get back to the office. I will be home at 4.”
We cleared the table and walked out of the apartment. Emily and I went into my apartment and Jessie continued to the elevator.
Emily and I worked on putting things into their place. Emily was a very verbal and intelligent 7 year old. We had a good conversation about many things. About 3:00 she started asking about her mom and I.
“Mom said you went to school together,” Emily said.
“Yes, high school,” I affirmed.
She paused then asked, “Mom said she went to high school with my dad.”
I didn’t like where I knew this was heading.
She paused again before asking, “Are you my dad?”
I answered softly, “No, Emily, I am sorry. I am not your dad.”
Emily frowned, her face was crestfallen, and tears appeared in her eyes.
“I didn’t think so. Mom would have told me. I have never met my dad,” she said sniffling. “Did you know my dad?”
I hesitated and then said, “I may have, if he went to high school with your mom and I.”
“I don’t even know his name,” she said still sniffling.
I walked over to her and gave her a hug. She stayed motionless for several minutes.
“Let’s stop working. Do you want to see my high school yearbook? There are pictures of your mom and pictures of me,” I suggested.
She backed up, her eyes brightened, she smiled, looked at me, and nodded. I had just put these on a bookshelf a few minutes ago. I retrieved my yearbooks and we sat down on my sofa. We spent the time up to 4:00 looking at the pictures in the yearbooks. She liked the cheerleader pictures of her mom and the picture of her mom as part of the homecoming court. I had forgotten that Tony, Emily’s dad, was Jessie’s partner in the homecoming court. I tried to move off that page, but Emily kept going back to it.
“My mom sure is pretty,” Emily stated. “Don’t you think so?”
“Yes, I do Emily,” I responded. “It’s almost 4:00. You should go home. You can come back another time.”
Just then there was a knock on the door. I opened the door to see Jessie standing there.
“Time to come home,” she said to Emily.
Emily said, “Bye Mr. Ben. Thank you for letting me help and for showing me the pictures.”
“Stop over anytime when your mom says it is okay,” I said. “Thanks for your help.”
Jessie smiled and thanked me as she shut the door behind them.
I continued to unpack and put things away for almost two hours. I ordered a pizza. A couple minutes later there was a knock on the door. Too soon for the pizza to arrive. I opened the door. Again it was Jessie with a shy, humble expression. She was dressed very nicely. It showed off her shapely figure, without being revealing.
“I have a favor to ask,” she said and paused. “I have a date tonight. My babysitter came down sick. Would you possibly be willing to watch Emily?”
“Yes, I will,” I agreed. “I just ordered a pizza. Emily can share it with me. When will you be home?”
“I should be home around 10. Emily can stay up until I get home,” Jessie said.
I left the door open. Soon Emily walked in.
“Thank you!” said Jessie as she kissed Emily goodbye.
We ate the pizza, played a couple of card games, then sat on the couch and watched some cartoons. A little after nine Emily laid down and put her feet in my lap. In a few minutes she was asleep. I turned to the news. A couple of minutes after 10 there was a knock on the door.
“Come in,” I said.
Jessie opened the door and walked in. She smiled when she saw Emily fast asleep. She came over and gently woke Emily up enough to have her walk next door.
“Thank you!” Jessie said as she closed the door behind her.
I hadn’t expected to be paid, but somehow I had expected more than a simple thank you.
The next day Jessie saw me in the hall and asked if I could watch Emily on Wednesday night. I agreed. Wednesday night came and Jessie and Emily came by at 6:00. They were having a disagreement in the hallway.
“I don’t want Tom to babysit me. I don’t like Tom,” Emily said loudly.
“You and Tom need to spend some time together. You need to get to know each other. We have been dating for awhile and you have only seen and spoken to him twice,” Jessie stated firmly.
She smiled at me and apologized.
“Have a good night with Mr. Ben,” said Jessie patting Emily on the head before walking to the stairs.
Emily went into the apartment.
“It’s his fault. He never comes upstairs to get mom. Tom just sits in his car out front. He’s kind of creepy. He looks at me weird. I don’t think he likes me,” Emily stated.
“Emily some people are just uncomfortable children, especially if they don’t have kids of their own,” I offered.
“You don’t have kids, but you are fun to be around,” Emily countered. “I think mom likes Tom too much.”
“What do you want to do?” I asked changing the subject.
She suggested card games. We played several games of a couple different card games. Emily played very well for a seven year-old. She didn’t just play cards, she played with strategy. When she got tired of cards she wanted to look at the yearbook pictures again. From the prior time she knew to look at the index in the back to find the pages her mother was on. Then she wanted to see where I was pictured. I wasn’t pictured in as many places as Jessie, but Emily had to see them all.
“You played basketball and were good at math,” Emily stated.
Basketball was obvious because of the team picture.
“How do you know I was good at math,” I asked.
“You won a math award and two people wrote that you helped them with their math,” Emily replied matter of factly.
“Yes, I am good at math. That is what got me interested in computers,” I said.
“Do you have a computer here?” she asked.
“I do, but it is a little late to start it up tonight,” I explained.
“Oh, ok I guess it is,” she said without any argument or disappointment.
Emily yawned several times, then lay down on the couch and was sleeping in a couple of minutes. I watched the news until there was a knock on the door at 9:45. I walked over and opened the door. It was Jessie. Her eyes were red like she had been crying.
“What’s wrong?” I asked.
“N.nothing,” she said and walked past me toward the couch.
“Emily time to go home,” Jessie said.
Emily mumbled something.
“I guess I am going to have to carry her,” Jessie said with a sad tone.
I offered to carry Emily and Jessie quickly agreed. We went next door and I put Emily in her bed. Jessie pulled the sheet and blanket up over Emily. I turned and walked out of the bedroom and headed for the front door. I heard the bedroom door close.
“Goodnight,” I said.
“C.can you st.stay and t.talk for a few minutes?” Jessie asked stuttering with a sad tone in her voice.
“Sure,” I agreed.
She sat at the table and I sat to her left.
“T.Tom doesn’t like children. He doesn’t want to be around them. He refused to babysit Saturday night. Then unloaded his dislike of children on me. I’m dating with a goal, a long term relationship with the right person. All Tom was looking for is sex. No commitment, especially to a woman with a child. I dumped him and took a cab home. I didn’t want to spend any more time with him,” she said.
I didn’t say anything for a while.
Finally I said, “It’s his loss. Emily is a great kid and you are a terrific woman.”
My words kind of tailed off at the end. I didn’t want her to think I was hitting on her, because of the situation.
“What’s going on Saturday night, where you need someone to watch Emily?” I asked.
“One of my girlfriends is getting married. Her bachelorette party is Saturday night,” she answered.
“I can watch Emily. I promised to show her my computer,” I offered.
“Thanks!” she said. “Why can’t I find guys like you to date?”
She leaned over and gave me a hug, not letting go for several minutes. I wondered why she didn’t think of me as dating material. Maybe she had been waiting for me to ask her. Again with the current situation I didn’t think now was the right time to ask. Beside up to now she had been dating Tom on a regular, steady basis.
“Thanks again!” she said. “Saturday night you had probably better watch Emily over here. I might be pretty late.”
She released the hug and sat back in her chair.
“Are you all right?” I asked.
“Yeah, I’m ok. Break-ups are hard,” she said. “Thanks for listening.”
I took that as my signal to get up and leave. I walked to the door and down to my apartment. My thoughts were on when to ask Jessie on a date without her still being on the rebound.
Saturday finally came. I had to take some diphenhydramine for my summer allergies. I still hadn’t decided what the best timing would be to ask her for a date. But I had decided I was going to start with an activity for both Emily and Jessie in case she wasn’t really interested in me. I took some more diphenhydramine during the day and then again just before 5. I put the bottle of medication in my pants pocket. I was at her door at 5:15. I knocked and Emily opened the door.
She smiled a huge smile, “Come in mom is still getting ready.”
I walked in and sat on the couch.
“Emily, go get a game you want to play,” I requested.
Emily happily ran to her bedroom. Soon I heard someone coming from the hallway. I looked up and Jessie was standing there in her bra and panties with a towel over her head drying her hair. I couldn’t help but stare at the gorgeous body standing about 12 feet away. Her curves were close to the classic hourglass shape. Her breasts were large, but well proportioned. Her legs were well toned and sleek. I know it was over seven years ago, however you would have never known she had been pregnant. My penis began to instinctively respond to what I was seeing.
“Emily, Mr. Ben will be hear soon. I am going to get dressed, so let him in when he knocks,” Jessie said before removing the towel.
Emily had walked up to her mother’s side with a game in her hands. Emily was watching me.
“Oh, Ben, I didn’t realize that you were here! Sorry!” Jessie apologized now holding the towel in front of her. “Emily you should have told me Ben was here.”
Jessie backed down the hallway to her room. Emily smiled and giggled after the bedroom door closed.
“How about Monopoly?” Emily asked.
I shook my head yes, even though I was surprised at the choice. Emily put the game on the table and started setting it up. I moved to the table. Emily began handing out the money for each of us in the denominations suggested in the game instructions. She had obviously done this before, because she did this from memory.
“I am the racecar. What piece do you want?” Emily asked as Jessie walked out now fully dressed.
She was gorgeous. Her dress looked like it had been made for her. It wasn’t revealing, but was very sexy. Again I began to get a bulge in my pants.
“It looks like you two are ready for a fun evening. I am heading out,” she said as she gave Emily a kiss. “Thanks again, Ben! I am not sure when I will be home.”
She left and Emily and I got back to the game. I picked the dog as my piece. My hard-on didn’t subside for over an hour. My mind kept going back to what I had seen. Maybe my mind was not on the game or Emily kept getting the rolls of the dice that she needed. She ended up the monopolies on both sides of the “Free Parking” space. She systematically built up to hotels on all six properties. I went bankrupt soon after. Emily had handled the banking duties with ease throughout the game. I was impressed. We had eaten the pizza that I had ordered and was delivered during the game.
“Emily, what kind of places do you like to go to or what do you like to do outside?”, I asked.
“I liked going to the zoo with my class before school ended,” she said immediately.
I knew the zoo she was talking about. Over the years it had been updated. Aside from the animal displays there was a botanical garden, a small amusement park, mini-golf, and a lake with canoes and water bikes. This would be the perfect place to take Jessie and Emily without it seeming like a date. I would ask Jessie if she and Emily would like to go there some Saturday.
Emily and I played a few card games after she put Monopoly away. After that we watched some television. She started yawning and I told her to go get dressed for bed. She came back in a few minutes and watched television for a few more minutes. She was yawning again. I looked at her.
“I know. Time for bed,” she said giving me a kiss on the cheek and went to her bedroom.
I again felt my allergies getting the best of me and took another dose of my medication. The TV droned on.
I must have fallen asleep. I woke up sometime later. I was in bed in my underwear. I was covered with a sheet and a light blanket. How had I gotten there? After I opened my eyes and my vision cleared, I realized I was not in my bedroom. I then realized that there was someone else in the bed with me. They were pressed up against my back with an arm around my waist and fingers on my stomach. I turned my head to see Jessie laying in bed behind me. I realized that I must have fallen asleep on the couch after taking the last dose of diphenhydramine for my allergies. But, how had I ended up here? I stretched my legs slowly without moving too much. Jessie’s fingers and hand started moving. Her fingers slipped under the waistband of my underwear. I jerked slightly.
“Good morning Ben! It’s just me, Jessie. I have been waiting for you to wake up. You sure sleep soundly,” Jessie whispered in my ear.
“How did I get here?” I asked.
“Do you not want to be here?” she said giggling.
“That’s definitely not what I said!” I answered quickly.
Jessie started explaining, “Last night when I got home I found you sound asleep on the couch. I tried to wake you with no luck. I thought about leaving you there to sleep, but you did not look comfortable. I managed to get you to your feet. I considered taking you to your apartment, but after a couple steps I knew it would probably not be possible. I also didn’t want someone to see us in the hallway and start asking questions. With some struggle I got you to my bedroom and had you sitting on the bed. I removed your shirt before you collapsed to your back on the bed. I removed your shoes and then your pants to make you more comfortable. I covered you, then I undressed and got into bed with you.”
I was still groggy. It must have been from the allergy medication. Maybe it caught up to me or maybe I took an extra dose without thinking. However, my mind now focused on the fact the Jessie and I were in bed together. I in only my underwear and Jessie was “undressed” whatever that meant. Her free hand was in my underwear and her hand wrapped itself around my manhood. I hadn’t realized how hard I had become until she began slowly pumping up and down my manhood. I moaned softly as she continued with the slow steady pace she began with. For the first time I realized her bare breasts were pressed into my back. Her nipples had noticeably hardened. I reached my free hand back between out bodies. I found her navel.
Jessie giggled, “That tickles. I wondered when you were going to actively participate.”
I moved lower finding a well trimmed patch of hair. I continued lower. I touched the top of her pussy lips. She let out an “ahhh” as I caressed the outside of the complete length of pussy moving up and down. I felt the heat between her legs increase. Jessie quivered and adjusted her position to give me better access without losing her grip on my rod. I felt her other hand which I thought was trapped under her body moved across my rear end and down my crack. It didn’t stop there. It tried to push between my legs. I bent my leg to allow it to continue on its journey. Her fingertips touched my scrotum. I jerked slightly and let out an “ohhh”.
“This is too clumsy. Turn over and face me,” Jessie commanded.
I quickly complied. I got to see her bare, wonderful breasts. I stared approvingly and with desire. She gently squeezed my balls, bringing me out of my reverie. “Mmm” exited my lips. I restarted tracing my fingers along her pussy lips. One on each side and one along her slit. My middle finger became moistened from the fluid seeping between her lips. The musky smell quickly reached my nose. I found it entrancing and breathed deeply taking it in. With my middle finger moistened I pushed it between her pussy lips beginning at the bottom I moved it around in small circles making my way up to toward the top. I was slow, deliberate, and methodical. I could tell I was doing something right because of her soft moans and the occasional pause in her attention to my genitals.
I was still looking at Jessie’s breasts with a strong desire to get my mouth and tongue on them. I must have licked my lips, because soon her lips pressed into mine. Her lips were full, soft and supple. Her tongue pushed for entry into my mouth. I opened my mouth and our tongues battled for position. My finger made it to her love hole. I pushed it inside her continuing to move it in small circles. When I got up to the second knuckle, Jessie took in a deep breath and then slowly let it out. When I had in inserted to its full length She repeated her deep breath. She had been increasing her pace on my penis as the temperature inside her increased. I hooked my finger and explored inside her. I found that special spot. Jessie jerked and her mouth left mine.
“Yes, yes! That is the spot,” she said more loudly than I had expected. “More! More!”.
I continued with my finger inside her. I pushed my thumb to the top of her slit and began to rub. Jessie shrieked, but quickly closed her mouth and buried her face in her pillow. Her body shuddered, then stiffened before spasming uncontrollably for some time. She looked at me panting.
“I have never had an orgasm during foreplay. That one was intense. Give me a little time to recover,” she managed to get out. “Then I will get back to you.”
I rolled on my back. She quickly moved next to me putting her head on my shoulder and I wrapped my arm around her.
She whispered in my ear, “We have to be careful not to wake Emily. After I couldn’t get you to your apartment last night, I realized I had never paid you for watching Emily.”
I started to object but she put her fingers to my mouth.
“Shhh,” she said. “This is your payment. At least a partial payment.”
Jessie got up on her hands and knees. She began by kissing me on my neck and chest. Her luscious breasts just out reach of my mouth and because of our positions it would have been awkward to reach them with my hands. I just relaxed and concentrated on the feeling of her lips on me. She moved down my stomach and toward my penis. I felt her fingers in my pubic hair, lightly scratching my skin. I tingled as my rod hardened again. Her other hand reached under my ball sack and lifted them cradling them in the palm of her hand. She rolled them around and scratched the loose skin between my balls. My penis was now standing straight up and moving with each heartbeat. Jessie giggled as she watched it bumping against her hand that was still playing with my pubic hair. She then used it to grab the base of my swaying pole, then her lips touched it’s tip. “Oooo” exited my lips. I pushed up against her lips hoping to get into her mouth. She obliged and her lips closed around the head of my penis. Jessie used her tongue on the tip and head. I writhed around on the bed. The wonderful sensation was flooding over me. I again pushed up and she took more of me into her mouth. I could already feel the exquisite pressure building inside me. It had been sometime since I had had sex of any kind. I held off as best I could. Then I reached the back of her mouth as she sucked me in deeper.
“I am going to cum soon,” I warned her.
She didn’t back off, but became more energized and intense in her efforts. I groaned and exploded into her mouth. She swallowed and continued sucking until the pulsations of my penis subsided. Jessie continued sucking and licking until I began to soften. She laid back in the same place she had been before while we both recovered.
“I want you inside me,” Jessie said.
I started to move.
“Would you use your mouth on my nipples first.” She requested. “You have been looking at them with desire the whole time.”
Jessie rolled on her back. I rolled on my side and began to lightly caress her breasts and nipples. They hardened. They became longer than other nipples I had seen. I took the first nipple in my mouth. I kissed and gently sucked on it. I licked the top as I sucked harder and harder. Jessie moaned loader as I sucked harder. I repeated this on her other breast. Jessie responded with continuing moans. I reached down between her legs and quickly found her clitoris. I gently circled it with my finger. Jessie writhed on the bed and started breathing short quick breaths with an occasional deep breath. I moved my mouth down to replace my finger. I licked her clit and then sucked on it just as I had her nipples. Jessie’s movement became move intense and she pushed my head tight against her pussy. It felt like steam coming from inside her. I nibbled gently on her clit. She jerked and shrieked.
“We need to be quieter,” Jessie said. “P.please come inside me. I want you inside when I climax.”
I smiled in amusement. I had been quiet, she was making the louder sounds. I quickly moved between her spreading legs. I positioned myself to enter. Just as I pushed past her pussy lips we heard the toilet flush. Emily was awake.
“Keep going. She won’t come in when the door is shut,” Jessie said.
Having sex with Jessie is something I had dreamed about since high school. I had jerked off many times thinking of her and picturing her naked body in my mind. Now it was about to happen.
I pushed slowly into her pausing occasionally to enjoy the exquisite feeling surging through my body. Her pussy was tighter than I had hoped. When I had fully penetrated her she clamped around me like no woman had done before. I began moving in and out slowly with short strokes. As I lengthened my strokes and increased the speed I got the sound that is made when the suction is right and the body parts mesh together well.
“I wondered where the word fuck had come from,” Jessie said. “Now I know.”
I continued almost exiting her before pumping back deep inside her. Jessie started moving around under me. I was nearing my climax and increased my speed. Both of us were breathing heavily. Jessie’s eyes were closed and she had started panting. I felt by balls tightening warning of the upcoming explosion. Jessie was making a small grunt each time I injected my rod into her. I groaned and flooded her with my sperm. Jessie arched her back and yelped just before putting her hand over her mouth. I kept pumping for about a minute before I slammed into her and remained there. Jessie shook and shuddered for a little longer before going limp. I rolled off Jessie on to my back. I looked over at Jessie with a big smile on my face. Her eyes were still closed with a contented smile on her face. I moved and kissed her shoulder. She opened her eyes put her hand on the back of my head and pulled me over for a very passionate kiss.
“I have a request,” she said with an almost frightened, serious tone.
“What do you want to ask?” I responded curiously.
“Since I broke up with my boyfriend Tom, I don’t have anyone to go to my girlfriend’s wedding with Emily and I on Saturday 2 weeks from now. Would you go with us?” she asked.
I was caught off guard, but recovered to answer, “Yes.”
“Good, I hate to be single and alone at a wedding. You get hit on by every single guy there,” she explained.
“Would you and Emily go with me to the zoo next Saturday?” I asked.
“Emily and I would be happy to go. She loves the zoo,” Jessie answered immediately. “Maybe you and I can go out for dinner sometime too.”
That’s how my romantic relationship with Jessie started.