Staying with Mrs. Wentworth, Day 03

Janine rubbed my ass while I poured and reached over and squeezed my thigh again when I sat back down. Mrs. Wentworth looked annoyed at Janine and then got nervous when Anita asked if Lana and I were serious. I said, truthfully, "It was our first date, really so it's hard to say."

Mrs. Wentworth becamse more at ease and said to Anita "but they made a very cute couple so I hope they go out again." I smiled and thought about what that meant.

The second bottle was soon gone even though only three of them were drinking it and Mrs. Wentworth sent me for a third which she had also put in the fridge. I was surprised because it seemed like a lot of wine but maybe she was expecting to drink that much.

Janine didn't know I could hear everything when I was in the kitchen and I heard her ask Mrs. Wentworth the minute I left, "Doris, he's adorable. Can I take him upstairs and fuck him in your bed?" Kim giggled, Anita said "I don't think your husband would approve," and Mrs. Wentworth said "you're such a bitch, Janine." But then they all laughed.

Of course it made me hard as a rock. I was contained but my bulge while not poking out was outlined by shorts and I realized the waiter pants weren't loose enough and so they showed it off instead of hiding it. I realized this when Kim was staring at my leg while I was serving Mrs. Wentworth and kept staring. Janine touched my ass again while I was serving and then told me she thought Kim wanted more tea. While I gave it to her, she didn't giggle but just stared.

Mrs. Wentworth didn't seem to notice her one friend touching me and the other less bold one staring openly at my bulge. I sort of resented that the pants and shorts that Mrs. Wentworth decided on actually showed me off like that. But I guess she didn't think about that and she didn't seem to notice anyway. We stayed there talking for a while. Mrs. Wentworth and Janine had most of the third bottle. In fact, Mrs. Wentworth had a lot, Janine not quite as much and Anita very little.

When they finally left it was getting dark. I held the door. Kim gave me a hug and Janine accidentally pushed her into me so my bulge pressed into her. She giggled and left. Anita also hugged me but more normally. Janine grabbed both of my ass cheeks, pulled me close and kissed me passionately before whispering "I wish I could take you home. I could teach you a lot more than your old teacher could." Then she walked past and slapped my ass, leaving me staring.

Mrs. Wentworth came back in after seeing them off and I followed her into the other room where she turned around and said "Stephen, my darling, you were just wonderful. I was so proud of you and so grateful!" And then she put both arms around me and hugged me very tight. I was so surprised and actually very happy to have helped that I didn't pay any attention to how I was positioned and where my bulge was. I was still pretty hard from Janine's good bye but Mrs. Wentworth didn't seem to notice it pressing into her. At least that's my guess because of how long the hug lasted.

She pulled me next to her on the couch. Then said "wait a minute." And got up and brought back a new bottle of wine and two clean glasses and poured us each a glass. I don't usually have any but it made me feel pretty sophisticated to be sharing with her. She'd had a lot of the first three bottles so she was maybe a little bit drunk. Not stupid drunk like your friends in college might get but happy.

She stretched out her legs on the coffee table and then tuned and said "help me off with my heels you helpful man." I helped take both of them off. I think women's high heels are rel sexy so I kind of enjoyed it. Also I made her turn a little to get at them which is actually a pretty good angle if you were trying to peek up a very long skirt. I wasn't trying, at least not on purpose, but since I could see I thought I would at least look a little. Between seeing up her skirt and the fact that the first foot I had let out of the shoe was resting on the spot where my hardon and leg were held tight together, I couldn't help staying pretty hard.

Then I noticed she was talking. I heard "...so I don't usually wear this dress but with them I feel a need to keep up a look. After all, Janine is the one who...well it doesn't matter. Does the dress look OK, Stephen, or is it boring?" She stood up and stared at me.

I decided to be honest. "It looks fine. You look good, I mean. It is a little boring though but it isn't like you could wear that red dress you wore the other night here, right?" She playfully kicked me, still standing up. "I thought so. I knew you liked that dress. Oh well, help me change now." I must have looked funny because she said "it's OK, silly boy. I'm sure you help your mommy all the time dressing and changing and finding things. I just need that kind of help now. After all, you've been so very helpful to me and my friends today."

Then she turned around and held up her hair. I helped lower the zipper on her dress because that's what she wanted obviously. With her back to me, she wiggled her arms out and it fell first to her waist and then to the floor. She stepped out of it with her back to me still. She was wearing a white bra and her panties were visible through sheer pantyhose. She bent down to pick up the dress at her legs causing once again her ass to collide with me. I wasn't complaining though. Then she walked away and started going up the stairs and asked "are you coming?" I didn't know what was going on again but I followed.

In her room, she started going through the closet and drawers like she was looking for something. I just stayed in the doorway and enjoyed the view. After a few minutes she bent down with her back to me and took down her pantyhose and took them off and laughed a little like we were sharing a joke. I was confused of course but maybe her being a little bit drunk explained everything.

But I wondered what was next. It wasn't that late and the dinner was more like a late lunch but it was after 7:00. It wasn't bedtime but she was looking at pajamas and nightgowns. She had me hold a few short satin nightgowns and robes while she looked. Then she took the black lace pair of panties I liked out of the laundry basket that was still on her bed and set them down. Turning to me, she looked up and down like she was evaluating me. "Hmmm, I think we'll watch a movie before bed or something so I should probably be careful. I think shorts and a top are the right thing. OK set the pile on the bed." I turned to go but she called out "Wait!"

She reached out and held both my hands and looked at me. "Darling, You look so much like a waiter and I just know that our guests appreciated your service and how perfect you looked." And then she hugged me again. This time her beautiful body just in her underwear pressing warm and tight against me. It's amazing I didn't explode. But I might have throbbed a little.

After a few seconds she looked concerned and pulled back and stared at my leg. Then she touched the lump in my pants. "Oh dear, he's been cooped up all day hidden away nice and proper so no one notices him. That's fine but I'm sure you shouldn't wear the shorts all day. Why don't you change too?" Then she patted my bulge and sent me along. It was weirdly erotic but at the same time in a manner that wasn't exactly seducing. It was a weird combination of motherly or something like that and also sort of bold because she touched what obviously hard even though not in a date kind of way.

I almost closed her door but she wagged her finger and said "open doors, always."

It felt good to let everything hang out. I liked being held in but my cock and balls needed some breathing space. I just changed into some loose shorts and boxers and a not tight shirt and went downstairs. She had gone first and was sitting on the couch with two glasses of wine again and a tray with crackers and cheese. I noticed she was wearing green shorts and a matching long top that almost hid the shorts.

The whole thing seemed really very elegant and sophisticated and grown up. That was really nice. It was like she knew we were adults, equals sort of. And she was treating me just like it. I sat down where she patted a spot on the short couch. I liked the way she looked. The pajamas were sexy in a way even though they were shorts not a skirt and I couldn't look up them. Not that I spend my life trying to look up skirts. I'm not a total pervert all the time. But they were nice. Green satin was sexy and we were close on the couch like old friends.

I could kind of tell from the way her upper body was that she wasn't wearing a bra under her nightshirt because even though she was in good shape there was a sagging sometimes in her upper body that made it clear her breasts weren't held up. I did notice once when I got up and was about to sit down that her legs were stretched out on the coffee table and propped up. She was less careful I guess because she was wearing shorts so I could see the loose patch of satin that went between her legs not completely covering the layer underneath. That's how I could tell she had the black lace panties I had folded and looked at on underneath everything. The first time I noticed, it made me pretty hard. I managed to stay pretty hard for a long time because she kept doing things like reaching across and touching me on the leg when something was funny in the movie or turning and smiling and I would see almost a little cleavage. Or she would stand up to reach across the table for the wine bottle or other things and the way she bent made her gorgeous ass very noticeable and just a few inches from me. I wanted to reach out and grab it but of course I didn't.

Because the whole time was like a sort of long tease and I was just sitting there enjoying it, I didn't pay much attention to the movie. It was an old movie. Black and white with people I didn't know and I'm glad there wasn't a test because I wasn't watching the TV at all. At one point I completely stopped looking at the TV because I noticed something. Mrs. Wentworth's pajama shirt was long but it was a little tight in the chest. I could see bumps that told me she had hard nipples. Maybe because it was cold a little or I was hoping it was from just being with me or something like that.

A few minutes later, there was a commercial in the movie and she stood up and told me, "You know, my nightshirt is long enough that I don't have to have these shorts on. I think I'd be more comfortable without them." And she carefully removed them in a way I couldn't see anything. She was correct that when standing up her shirt covered her panties. But it wasn't by much and when she sat I saw a lot of leg because we weren't very far apart. Then she asked me to go get the remaining little bit of wine in the kitchen that was almost empty even though her glass was pretty full. When I came back, she still wasn't careful how she sat, forgetting she took her shorts off I guess, and I could see a lot. I tried hard not to stare but I saw all her panties and they were almost completely in the open. You have no idea how hard that made me. I almost wished I wasn't just wearing loose shorts with just boxers under them because I was really exposed.

I sat back down and continued staring at Mrs. Wentworth's breasts while she watched the TV. I couldn't exactly cover up myself but as long as she looked at the TV, I was OK. She stood up again and bent over causing her shirt to rise in back and expose the panties. They had a black lace back almost like netting. They looked better tightly covering her ass than when I folded them. If this was a movie I'd have jacked off and cum in about 10 seconds. But I tried to stay cool. She sat down again but closer. Our legs almost touched and she smiled at me and drank more wine. I'd had about one full glass but she had had over the last five hours a whole bunch more.

She looked directly at the pressing bulge in my pants and sighed and patted it. "Oh, my sweet Stephen, I feel so bad. The whole day must have been hard for you with that awful Janine just teasing you and you're still under pressure from it now! I feel terrible. You need some room. Now don't worry, sweetheart. Mrs. Wentworth understands how men and their parts work. Stand up and take off your shorts so you aren't pressed so much. Don't be shy. We're alone in our house and it's perfectly fine and natural. Right now, please."

What could I say? I sort of agreed. And I couldn't protest so I stood up and did it while she leaned forward a little like she was watching and almost staring. When I dropped the shorts, I only had on boxers and my cock was poking straight out. Dropping the shorts almost made it bounce. Fortunately, it was away from the fly opening so I didn't spring out. Mrs. Wentworth reached a finger out and poked the tip which was hidden but made a wet spot with pre-cum. "Oh, look. Poor thing is actually leaking. I'm glad we let him have some room." Then she leaned back and watched the movie.

Talk about mixed signals. Oh well, I sat back down, more comfortable even though I was sitting next to this older woman with a practically throbbing hardon almost visible. I was sure it would calm down with fewer peeks at her and a slower evening. It started to go down a lot pretty soon and she never looked directly at it. But when she stood again and bent, the tease of her panties was too much. It was worse when she twisted as she sat. Her shirt rose more than she probably thought and it was twisted so it was tight enough on her breast and facing me that I almost had to stare. And then she leaned and put her head against me like she was tired. I had to close my eyes for a second not to explode.

She was sort of whispering with her head against my neck, "it's terrible what they did to you and made you so frustrated all day long. I'm glad I was a perfect lady at dinner and didn't contribute to that!" I couldn't tell her that it wasn't just her friend at dinner but it more her and her awesome look all day that did this so I didn't say anything.

Then she looked down and poked my hard on and giggled. She actually giggled. It was weird. "Hmmm. It isn't healthy is it, darling? It's not good for a virile, handsome, fit young man to be so frustrated and backed up. And it was my friends so it's sort of my fault." I just kept quiet because her hand went down and reached in and pulled me out of my shorts. It was all happening in slow motion like a dream. I mean her hand actually had just pulled my throbbing cock out of my shorts. Then her head moved down and suddenly her tongue licked the tip and then I was in her mouth. I was almost shocked.

I looked down and only saw the back of her head but I could feel her warm and wet mouth all around it until I felt her head pop off with a smacking noise. "Yes," she whispered very roughly like she was suddenly hoarse, "the only proper thing to do is release the pressure." It was like she was talking to herself though.

I'd love to say I lasted for like a half an hour. But I didn't. This was the first time a woman, a real woman, had even thought about sucking on me. It was amazing and I had been so close to cumming off and on all day. I didn't know at the time if she was good or bad because it was my first blowjob ever but she was actually really good. It was less than five minutes before I was tense and started to spurt. Her hand encouraged it all out even when she popped off. When I was done, I sat there catching my breath but she stayed there with her head down.

After a minute or two, I heard her say very quietly, "I have to go to bed." The she stood up and turned around and said "good night dear, thank you for all your help today." It was as if nothing had happened except she had a few spots on her nightshirt and something on her chin. I didn't get a chance to say anything, she just hurried away and up to bed.

After a few minutes, I got up and started cleaning up things before going up. I was still in shock that it happened. Mrs. Wentworth had just given me a blowjob. I had no idea what I was going to say to her on the way to bed or in the morning.

It was about twenty minutes later when I went up. I went to her room to say good night but she was under her covers and obviously asleep so I just looked for a minute and finally went on to my room. For the first time there, I didn't masturbate before going to sleep. I just tried to think of what to say in the morning and how different everything was going to be tomorrow.